You are on page 1of 174

BIOCHEMISTRY

BIOCHEMISTRY
FILS
FILS
LECTURER: LECTURER:
Biochemist Dr. Bogdan ico!ae Mano!esc" Biochemist Dr. Bogdan ico!ae Mano!esc"
Fac"!t# o$ %&&!ied Chemistr# and Science o$ Fac"!t# o$ %&&!ied Chemistr# and Science o$
Materia!s Materia!s

Biochemistry: Biochemistry:

studies: studies:

the biomolecules the biomolecules

the reactions that take place in the living cells the reactions that take place in the living cells

branches: branches:

descriptive biochemistry: descriptive biochemistry:

presents the major classes of biomolecules and their chemical presents the major classes of biomolecules and their chemical
properties properties

metabolism: metabolism:

presents the reactions that take place in the living cells presents the reactions that take place in the living cells

in order to understand biochemistry we need some basic in order to understand biochemistry we need some basic
knowledge of: knowledge of:

organic chemistry organic chemistry

physiology physiology

cell biology cell biology

genetics genetics
Introduction Introduction

The main topics of the course The main topics of the course: :

carbohydrates carbohydrates

lipids lipids

nucleic acids nucleic acids

amino acids amino acids

proteins: proteins:

presentation of diferent types of proteins, including enzymes presentation of diferent types of proteins, including enzymes

vitamins vitamins

general presentation of metabolism: general presentation of metabolism:

carbohydrate metabolism carbohydrate metabolism

fatty acids metabolism fatty acids metabolism


Introduction Introduction

Biochemistry some landmarks: Biochemistry some landmarks:

riedrich ! riedrich !" "hler #$%&& $%%'(: hler #$%&& $%%'(:

)rst synthesis of an organic compound from an inorganic )rst synthesis of an organic compound from an inorganic
one #$%'%(: one #$%'%(:

denied * denied *the vitalist theory the vitalist theory* there is no * * there is no *vital force vital force* re+uired * re+uired
to e,plain life at molecular level to e,plain life at molecular level

-ouis .asteur #$%'' $%/0(: -ouis .asteur #$%'' $%/0(:

studied the fermentation of sugar to alcohol by yeasts studied the fermentation of sugar to alcohol by yeasts

coined the term * coined the term *ferments ferments* #arround $%0&(: * #arround $%0&(:

the conversion of sugar into alcohol could only occur in living yeast the conversion of sugar into alcohol could only occur in living yeast
cells #he belived in the e,istence of a *vital force*( cells #he belived in the e,istence of a *vital force*(
Introduction Introduction

Biochemistry some landmarks: Biochemistry some landmarks:

!ilhelm riedrich 1uhne #$%23 $/&&(: !ilhelm riedrich 1uhne #$%23 $/&&(:

coined the term * coined the term *enzyme enzyme* #greek: * #greek: en en, in 4 , in 4 zyme zyme, yeast( , yeast(

emphasized the fact that not the yeast cell catalyzes the emphasized the fact that not the yeast cell catalyzes the
conversion of sugar into alcohol, but rather something found inside conversion of sugar into alcohol, but rather something found inside
the cell the cell

5duard Buchner #$%6& $/$3(: 5duard Buchner #$%6& $/$3(:

obtained in $%/3 a free7cell yeast e,tract that could carry out the obtained in $%/3 a free7cell yeast e,tract that could carry out the
synthesis of alcohol from sugar #alcoholic fermentation( synthesis of alcohol from sugar #alcoholic fermentation(

demonstrated the this conversion is catalyzed by something which demonstrated the this conversion is catalyzed by something which
is located inside the yeast cells is located inside the yeast cells

was awarded the 8obel .rize for 9hemistry #$/&3( * was awarded the 8obel .rize for 9hemistry #$/&3( *for his for his
biochemical researches and his discovery of cell-free fermentation biochemical researches and his discovery of cell-free fermentation* *
Introduction Introduction

Biochemistry some landmarks: Biochemistry some landmarks:

:ermann 5mil -ouis ischer #$%0' $/$/(: :ermann 5mil -ouis ischer #$%0' $/$/(:

made studies concerning the chemistry of sugars, amino acids, made studies concerning the chemistry of sugars, amino acids,
purines purines

discovered that glycolytic enzymes can distinguish between discovered that glycolytic enzymes can distinguish between
stereoisomeric sugars stereoisomeric sugars

formulated * formulated *the lock-and-key hypothesis the lock-and-key hypothesis* of enzyme action: * of enzyme action:

the specifcity of an enzyme (the lock) for its substrate (the key) the specifcity of an enzyme (the lock) for its substrate (the key)
arises from their geometrically complementary shapes arises from their geometrically complementary shapes

was awarded 8obel .rize for 9hemistry #$/&'( * was awarded 8obel .rize for 9hemistry #$/&'( *in recognition in recognition
of the extraordinary services he has rendered by his work on of the extraordinary services he has rendered by his work on
sugar and purine synthesis sugar and purine synthesis* *
Introduction Introduction

Introduction Introduction

Biochemistry some landmarks: Biochemistry some landmarks:

crystalization of the frst enzyme crystalization of the frst enzyme: :

urease from jack bean urease from jack bean

was made by ;ames Batcheller <umner #$%%3 $/00(: was made by ;ames Batcheller <umner #$%%3 $/00(:

crystallized other enzymes: catalase, pepsin crystallized other enzymes: catalase, pepsin

was awarded the 8obel .rize for 9hemistry #$/=6( for was awarded the 8obel .rize for 9hemistry #$/=6( for
crystallization of enzymes crystallization of enzymes

determination of the complete sequence of a protein determination of the complete sequence of a protein: :

bovine insulin #$/0' $/02( bovine insulin #$/0' $/02(

was made by rederick <anger #$/$% '&$2(: was made by rederick <anger #$/$% '&$2(:

used for se+uencing $7>uoro7',=7dinitrobenzene # used for se+uencing $7>uoro7',=7dinitrobenzene #anger anger!s reagent !s reagent( (

was awarded twice the 8obel .rize for 9hemistry: was awarded twice the 8obel .rize for 9hemistry:

$/0% * $/0% *for his work on the structure of proteins" especially that of for his work on the structure of proteins" especially that of
insulin insulin* *

$/%& * $/%& *for###contributions concerning the determination of base for###contributions concerning the determination of base
sequences in nucleic acids sequences in nucleic acids* *
Introduction Introduction

Introduction Introduction

Biochemistry some landmarks: Biochemistry some landmarks:

determination of the $% structure of a protein (&-ray determination of the $% structure of a protein (&-ray
analysis) analysis): :

sperm whale myoglobin #;ohn 1endrew, $/03( sperm whale myoglobin #;ohn 1endrew, $/03(

human and horse hemoglobin #?a, .erutz, $/6%( human and horse hemoglobin #?a, .erutz, $/6%(

?a, .erutz #$/$= '&&'( and ;ohn 1endrew #$/$3 $//3( ?a, .erutz #$/$= '&&'( and ;ohn 1endrew #$/$3 $//3(
were awarded with the 8obel .rize for 9hemistry in $/6' were awarded with the 8obel .rize for 9hemistry in $/6'

identifcation of nucleic acids as informational molecules identifcation of nucleic acids as informational molecules: :

through the research made by @swald Theodor Avery #$%33 through the research made by @swald Theodor Avery #$%33
$/00(, 9olin ?unro ?ac-eod #$/&/ $/3'(, ?aclyn ?c9arty $/00(, 9olin ?unro ?ac-eod #$/&/ $/3'(, ?aclyn ?c9arty
#$/$$ '&&0(, Alfred :ershey #$/&% $//3(, ?artha 9hase #$/$$ '&&0(, Alfred :ershey #$/&% $//3(, ?artha 9hase
#$/'3 '&&2( #$/'3 '&&2(

two major e,periments: two major e,periments:

the Avery ?ac-eod ?c9arty e,periment the Avery ?ac-eod ?c9arty e,periment

the :ershey 9hase e,periment the :ershey 9hase e,periment


Introduction Introduction

Biochemistry some landmarks: Biochemistry some landmarks:

the Avery ?ac-eod ?c9arty e,periment: the Avery ?ac-eod ?c9arty e,periment:

used two strains of used two strains of treptococcus pneumoniae treptococcus pneumoniae: :

< #smooth( strain < #smooth( strain

B #rough( strain B #rough( strain

< strain characteristics: < strain characteristics:

the cells produce a gelatinous polysaccharide coating which the cells produce a gelatinous polysaccharide coating which
enables the bacterial cells to recognize and bind to host cells enables the bacterial cells to recognize and bind to host cells

can produce pneumonia # can produce pneumonia #virulent strain virulent strain( (

the colonies are big the colonies are big

B strain characteristics: B strain characteristics:

the cells do not produce the gelatinous polysaccharide coating the cells do not produce the gelatinous polysaccharide coating

can not produce pneumonia # can not produce pneumonia #nonvirulent strain nonvirulent strain( (

the colonies are very small the colonies are very small
Introduction Introduction

Biochemistry some landmarks: Biochemistry some landmarks:

the Avery ?ac-eod ?c9arty e,periment: the Avery ?ac-eod ?c9arty e,periment:

mi,ing B cells with a cell7free e,tract of < cells, the B cells mi,ing B cells with a cell7free e,tract of < cells, the B cells
became virulent # became virulent #' cells were transformed into cells ' cells were transformed into cells( (

+uestion: +uestion: ()*+ (* +), -*+.', /0 +), +'*-0/'1I-2 ()*+ (* +), -*+.', /0 +), +'*-0/'1I-2
*2,-+3 *2,-+3

C8A was the transforming agent because: C8A was the transforming agent because:

it had all the characteristics of C8A it had all the characteristics of C8A

contained no detectable proteins #proteins were removed with contained no detectable proteins #proteins were removed with
proteases( proteases(

it was unafected by enzymes which catalyze the hydrolysis of it was unafected by enzymes which catalyze the hydrolysis of
proteins and B8A proteins and B8A

it was sensitive to enzyme that hydrolyze C8A #C8Ases( it was sensitive to enzyme that hydrolyze C8A #C8Ases(

%-* I +), 4*''I,' /0 +), 2,-,+I4 I-0/'1*+I/-5 %-* I +), 4*''I,' /0 +), 2,-,+I4 I-0/'1*+I/-5
Introduction Introduction

Biochemistry some landmarks: Biochemistry some landmarks:

the :ershey 9hase e,periment: the :ershey 9hase e,periment:

used the bacteriophage T' grown on used the bacteriophage T' grown on ,scherichia coli ,scherichia coli

the the ,# coli ,# coli cells were grown on a medium containing the cells were grown on a medium containing the
radioactive isotopes: radioactive isotopes:
2' 2'
. #only the nucleic acids contain .( . #only the nucleic acids contain .(
20 20
< #only the proteins contain <( < #only the proteins contain <(
Introduction Introduction

Biochemistry some landmarks: Biochemistry some landmarks:

the :ershey 9hase e,periment: the :ershey 9hase e,periment:

these phages were added to an unlabeled these phages were added to an unlabeled ,# coli ,# coli culture culture

after a time the culture was put in a blender: after a time the culture was put in a blender:

the phage ghosts were removed from the bacterial cells the phage ghosts were removed from the bacterial cells

the phage ghosts were separated from the bacterial cells through the phage ghosts were separated from the bacterial cells through
centrifugation centrifugation

the distribution of the isotopes: the distribution of the isotopes:


2' 2'
. was located inside the bacterial cells . was located inside the bacterial cells
20 20
< was located in the phage ghosts < was located in the phage ghosts

2&D of the 2&D of the


2' 2'
. isotope located inside 5E coli cells appeared in . isotope located inside 5E coli cells appeared in
the progeny phages the progeny phages

%-* I +), 4*''I,' /0 +), 2,-,+I4 I-0/'1*+I/-5 %-* I +), 4*''I,' /0 +), 2,-,+I4 I-0/'1*+I/-5
Introduction Introduction

Introduction Introduction
4,-+'I0.2*+I/-
0I'+ 2,-,'*+I/- /0 6)*2,

Biochemistry some landmarks: Biochemistry some landmarks:

determination of the $% structure of %-* determination of the $% structure of %-*: :

through F7ray difraction analysis: through F7ray difraction analysis:

Bosalind ranklin #$/'& $/0%( Bosalind ranklin #$/'& $/0%(

the double7helical model of the C8A molecule was proposed the double7helical model of the C8A molecule was proposed
by: by:

;ames !atson #$/'% ( ;ames !atson #$/'% (

rancis 9rick #$/$6 '&&%( rancis 9rick #$/$6 '&&%(

;ames !atson, rancis 9rick and ?aurice !ilkins were ;ames !atson, rancis 9rick and ?aurice !ilkins were
awarded the 8obel .rize in .hysiology and ?edicine #$/6'( awarded the 8obel .rize in .hysiology and ?edicine #$/6'(
for * for *their discoveries concerning the molecular structure of their discoveries concerning the molecular structure of
nucleic acids and its signifcance for information transfer in nucleic acids and its signifcance for information transfer in
living material living material* *
Introduction Introduction

Introduction Introduction
F7ray photograph made by BE ranklin
The double7heli, of the C8A proposed by !atson and 9rick

The chemical elements of life: The chemical elements of life:

elemental composition of the human body: elemental composition of the human body:

abundant elements: abundant elements:

9, :, 8, @, . and < 9, :, 8, @, . and <

account for about /3D of the dry weight account for about /3D of the dry weight

less abundant elements: less abundant elements:

'2 elements present as ions #8a '2 elements present as ions #8a
4 4
, 1 , 1
4 4
, ?g , ?g
'4 '4
, 9a , 9a
'4 '4
, 9l , 9l
7 7
, etc( , etc(

trace elements: trace elements:

G, 9r, ?o, H, <e etc G, 9r, ?o, H, <e etc

biochemical reactions: biochemical reactions:

involve the same functional groups as in organic chemistry involve the same functional groups as in organic chemistry

are similar to the reactions that take place are similar to the reactions that take place in vitro in vitro #in the organic #in the organic
chemistry lab( chemistry lab(

are catalyzed by enzymes are catalyzed by enzymes


Introduction Introduction

@bservations: @bservations:

red the most abundant elements red the most abundant elements

purple less abundant, but essential for all cells purple less abundant, but essential for all cells

dark and light blue trace elements #more common and less dark and light blue trace elements #more common and less
common, respectively( common, respectively(
Introduction Introduction

Introduction Introduction

The cell the basic unit of life: The cell the basic unit of life:

the cell is the morphological unit of all livings: the cell is the morphological unit of all livings:

a concept introduced in $%2% #?atthias <chleiden, Theodor a concept introduced in $%2% #?atthias <chleiden, Theodor
<chwann( <chwann(

classi)cation of cells: classi)cation of cells:

prokaryotic cells prokaryotic cells: :

greek: greek: pro pro, before 4 , before 4 karyon karyon, kernelInut , kernelInut

lack a true nucleus lack a true nucleus

very simple cells very simple cells

eukaryotic cells eukaryotic cells: :

greek: greek: eu eu, goodItrue 4 , goodItrue 4 karyon karyon, kernelInut , kernelInut

have a true nucleus have a true nucleus

very comple, cells very comple, cells


+he cell +he cell

.rokaryotic cells: .rokaryotic cells:

small cells: small cells:

$ $& $ $& J Jm m

K K &,$D the size of a typical animal cell &,$D the size of a typical animal cell

three basic shapes: three basic shapes:

spheroidal cells # spheroidal cells #cocci cocci( (

rodlike cells # rodlike cells #bacilli bacilli( (

helically coiled cells # helically coiled cells #spirilla spirilla( (

general design of a prokaryotic cell: general design of a prokaryotic cell:

cell membrane #plasma membrane(: cell membrane #plasma membrane(:

lipid bilayer that contains embeded proteins lipid bilayer that contains embeded proteins

cell wall: cell wall:

rigid structure rigid structure

provides strength and keep the cell provides strength and keep the cellLs shape Ls shape

enables the cells to live in a hypotonic environment enables the cells to live in a hypotonic environment
+he cell +he cell

.rokaryotic cells: .rokaryotic cells:

general design of a prokaryotic cell: general design of a prokaryotic cell:

cytosolIcytoplasm: cytosolIcytoplasm:

a+ueous milieu a+ueous milieu

contains all the enzymes and proteins of the cell contains all the enzymes and proteins of the cell

nucleoid: nucleoid:

the genetic material of the cell the genetic material of the cell

one circular chromosome condensed with proteins one circular chromosome condensed with proteins

ribosomes: ribosomes:

responsible for proteins synthesis responsible for proteins synthesis

bacterial appendages: bacterial appendages:

>agella #singular, >agellum( locomotion >agella #singular, >agellum( locomotion

pili involved in the transfer of C8A between cells # pili involved in the transfer of C8A between cells #sexual sexual
con7ugation con7ugation( (
+he cell +he cell

+he cell +he cell

.rokaryotic cells: .rokaryotic cells:

the outer membrane: the outer membrane:

Mram7positive bacteria: Mram7positive bacteria:

lack an outer membrane lack an outer membrane

the cell wall is thick # the cell wall is thick #K K '0& '0& N N( (

Mram7negative bacteria: Mram7negative bacteria:

have an outer membrane have an outer membrane

the cell wall is thin # the cell wall is thin #K K 2& 2& N N( (

the Mram stain: the Mram stain:

developed by 9hristian Mram #$%%=( developed by 9hristian Mram #$%%=(

principle of the method: principle of the method:

2ram-positive bacteria 2ram-positive bacteria the dye used reach the cell wall because the dye used reach the cell wall because
of the lack of the outer membrane of the lack of the outer membrane

2ram-negative bacteria 2ram-negative bacteria the dye used do not reach the cell wall the dye used do not reach the cell wall
because of the presence of the outer membrane because of the presence of the outer membrane
+he cell +he cell

5ukaryotic cells: 5ukaryotic cells:

large cells: large cells:

diameter of $& $&& diameter of $& $&& J Jm m

shape of the cells: shape of the cells:

enormous diversity enormous diversity

the shape of a cell is the conse+uence of its functional the shape of a cell is the conse+uence of its functional
specialization specialization

general design of an eukaryotic cell: general design of an eukaryotic cell:

cell membraneIplasma membrane cell membraneIplasma membrane

cytosolIcytoplasm cytosolIcytoplasm

organelles: organelles:

nucleus nucleus

Molgi apparatus Molgi apparatus

mitochondria mitochondria

lysosomes lysosomes

endoplasmic reticulum endoplasmic reticulum

ribosomes ribosomes
+he cell +he cell

+he cell +he cell

5ukaryotic cells: 5ukaryotic cells:

organelles have diferent functions: organelles have diferent functions:


+he cell +he cell

Types of organisms: Types of organisms:

prokaryotes: prokaryotes:

only single7celled organisms only single7celled organisms

have two major advantages: have two major advantages:

simplicity simplicity

miniaturization miniaturization

classi)cation: classi)cation:

bacteria bacteria

cyanobacteria cyanobacteria

rapid growth rate adaptability to ecological niches in which rapid growth rate adaptability to ecological niches in which
there can be drastic >uctuations of the nutrients there can be drastic >uctuations of the nutrients
+he cell +he cell

Types of organisms: Types of organisms:

eukaryotes: eukaryotes:

in respect to the number of cells: in respect to the number of cells:

unicellular organisms unicellular organisms

pluricellular organisms pluricellular organisms

advantage: advantage:

comple,ity comple,ity

can adapt to stable environments with limited nutrients can adapt to stable environments with limited nutrients

classi)cation: classi)cation:

plants plants

animals animals

fungi fungi

protists protists
+he cell +he cell

The principle of hierarchical organization of life: The principle of hierarchical organization of life:

living things #uni7 and pluricellular( are enormously comple, living things #uni7 and pluricellular( are enormously comple,

there are several levels of organization: there are several levels of organization:

atoms atoms

molecules molecules

macromolecules macromolecules

organelles organelles

cells cells

tissues tissues

organs organs

organism organism

the properties of one level can not be predicted only by the the properties of one level can not be predicted only by the
properties of the previous level properties of the previous level

some organisms lack certain levels of organization some organisms lack certain levels of organization
+he cell +he cell
C
O
M
'
L
E
(
I
T
Y


9arbohydrates: 9arbohydrates:

the most abundant compounds on 5arth: the most abundant compounds on 5arth:

K K 0&D of the dry weight of the biomass 0&D of the dry weight of the biomass

$& $&
$= $=
$& $&
$0 $0
kg celuloseIyear kg celuloseIyear

diferent terminology for these compounds: diferent terminology for these compounds:

carbohydrates carbohydrates: :

makes reference to the general formula 9 makes reference to the general formula 9
n n
#: #:
' '
@( @(
m m
#n #n O 2, n O m( O 2, n O m(

the term *carbohydrates* it is not fully correct as these compounds the term *carbohydrates* it is not fully correct as these compounds
are not * are not *hydrates of carbon hydrates of carbon* #do not contain intact : * #do not contain intact :
' '
@ molecules( @ molecules(

there are compunds that belong to this class but do not have the there are compunds that belong to this class but do not have the
9 9
n n
#: #:
' '
@( @(
m m
general formula #C7glucosamine P 9 general formula #C7glucosamine P 9
6 6
: :
$2 $2
@ @
0 0
8( 8(

sugars sugars: :

makes reference to the sweet taste of some compounds from this makes reference to the sweet taste of some compounds from this
class class

not all compounds belonging to this class have this property not all compounds belonging to this class have this property

unrelated compounds have a sweet taste 7 unrelated compounds have a sweet taste 7 (,,+,-,' (,,+,-,'

saccharides saccharides: :

greek: greek: sakkharon sakkharon sugarcane sugarcane


4arbohydrates 4arbohydrates

!here came from carbohydratesQ !here came from carbohydratesQ

carbohydrates are synthesized through carbohydrates are synthesized through 6)/+/8-+),I 6)/+/8-+),I: :

conversion of 9@ conversion of 9@
' '
and : and :
' '
@ into glucose and @ @ into glucose and @
' '

light reactions light reactions: :

use light energy to produce 8AC.: and AT. use light energy to produce 8AC.: and AT.

convert light energy into chemical energy #AT., 8AC.:( convert light energy into chemical energy #AT., 8AC.:(

dark reactions dark reactions: :

do not take place in dark, but are not directly dependent on light do not take place in dark, but are not directly dependent on light

enables the conversion of 9@ enables the conversion of 9@


' '
into glucose with the energy from into glucose with the energy from
AT. and 8AC.: AT. and 8AC.:

9alvin cycle #9 9alvin cycle #9


2 2
pathway( pathway(
4arbohydrates 4arbohydrates

4arbohydrates 4arbohydrates

9arbohydrates classi)cation: 9arbohydrates classi)cation:

simple carbohydrates: simple carbohydrates:

?@8@<A99:ABHC5< ?@8@<A99:ABHC5<

comple, carbohydrates: comple, carbohydrates:

CH<A99:ABHC5< ' sugar units CH<A99:ABHC5< ' sugar units

@-HM@<A99:ABHC5< 2 to $& sugar units @-HM@<A99:ABHC5< 2 to $& sugar units

.@-R<A99:ABHC5< more than $& sugar units .@-R<A99:ABHC5< more than $& sugar units

classi)cation of polysaccharides #glycans(: classi)cation of polysaccharides #glycans(:

:@?@.@-R<A99:ABHC5<: :@?@.@-R<A99:ABHC5<:

through hydrolysis gave rise to just one monosaccharide through hydrolysis gave rise to just one monosaccharide

e,amples: glycogen, starch, cellulose e,amples: glycogen, starch, cellulose

:5T5B@.@-R<A99:ABHC5<: :5T5B@.@-R<A99:ABHC5<:

through hydrolysis gave rise to two ore more diferent through hydrolysis gave rise to two ore more diferent
monosaccharides monosaccharides

e,amples: glycosaminoglycans e,amples: glycosaminoglycans


4arbohydrates 4arbohydrates

Types of formulas used in the chemistry of carbohydrates: Types of formulas used in the chemistry of carbohydrates:

4ram representations 4ram representations: :

usefull only for carbohydrates with one chiral carbon usefull only for carbohydrates with one chiral carbon

0ischer pro7ections 0ischer pro7ections: :

used very fre+uent used very fre+uent

can be open7chain representations and cyclic can be open7chain representations and cyclic

)aworth pro7ections )aworth pro7ections: :

used very fre+uent used very fre+uent

1ills representations 1ills representations: :

used not so fre+uent used not so fre+uent

conformational representations conformational representations: :

indicate the real 2C structure of a carbohydrate molecule indicate the real 2C structure of a carbohydrate molecule
4arbohydrates 4arbohydrates

?onosaccharides: ?onosaccharides:

de)nition: de)nition:

aldehydes or ketone derivatives of straight-chain polyhydroxy aldehydes or ketone derivatives of straight-chain polyhydroxy
alcohols containing at least three carbon atoms alcohols containing at least three carbon atoms

classi)cation according to carbonyl group: classi)cation according to carbonyl group:

aldoses polyhydro,y aldehydes #* aldoses polyhydro,y aldehydes #*aldo aldo* is for aldehyde( * is for aldehyde(

ketoses polyhydro,y ketones #* ketoses polyhydro,y ketones #*keto keto* is for ketone( * is for ketone(

classi)cation according to the number of carbon atoms: classi)cation according to the number of carbon atoms:

trioses 2 carbon atoms trioses 2 carbon atoms

tetroses = carbon atoms tetroses = carbon atoms

pentoses 0 carbon atoms pentoses 0 carbon atoms

he,oses 6 carbon atoms he,oses 6 carbon atoms


4arbohydrates 4arbohydrates

?onosaccharides how to make their namesQ ?onosaccharides how to make their namesQ

we need the following informations: we need the following informations:

carbonyl group: carbonyl group:

pre),es pre),es aldo7 aldo7I Iketo7 keto7

number of carbon atoms: number of carbon atoms: 7tri7 7tri7, , 7tetr7 7tetr7, , 7pent7 7pent7, , 7he,7 7he,7

suS, suS, 7ose 7ose #indicates that the compound is a carbohydrate( #indicates that the compound is a carbohydrate(
4arbohydrates 4arbohydrates

?onosaccharides the CI- convention: ?onosaccharides the CI- convention:

glyceraldehyde: glyceraldehyde:

it is the simplest aldose #more speci)c it is the simplest aldose #more speci)c aldotriose aldotriose( (

it has a chiral carbon atom it has two enantiomers it has a chiral carbon atom it has two enantiomers

we use the ischer projections: we use the ischer projections:

horizontal lines bonds coming out of the plane horizontal lines bonds coming out of the plane

vertical lines bonds going into the plane vertical lines bonds going into the plane
4arbohydrates 4arbohydrates

?onosaccharides the CI- convention: ?onosaccharides the CI- convention:

how to move ischer projections: how to move ischer projections:

rotation with $%& rotation with $%&T T in the plane is allowed: in the plane is allowed:

the same substituents go into and come out of the plane the same substituents go into and come out of the plane

rotation with /& rotation with /&T T and '3& and '3&T T is forbiden: is forbiden:

e,change the groups that go into and come out of the plane e,change the groups that go into and come out of the plane
4arbohydrates 4arbohydrates

?onosaccharides the CI- convention: ?onosaccharides the CI- convention:

ischer projections of glyceraldehyde: ischer projections of glyceraldehyde:

C7glyceraldehyde the 7@: at 9 C7glyceraldehyde the 7@: at 9


' '
is placed on the right is placed on the right

-7glyceraldehyde the 7@: at 9 -7glyceraldehyde the 7@: at 9


' '
is placed on the left is placed on the left

ischer projections of other carbohydrates: ischer projections of other carbohydrates:

the most o,idized 9 atom is drawn at the top of the ischer the most o,idized 9 atom is drawn at the top of the ischer
projection projection

9 9
$ $
for aldoses for aldoses

9 9
' '
for ketoses for ketoses

for each new 9 atom the 7@: group can be placed on the right for each new 9 atom the 7@: group can be placed on the right
or on the left or on the left
4arbohydrates 4arbohydrates

?onosaccharides con)gurational families: ?onosaccharides con)gurational families:

con)gurational families: con)gurational families:

%-sugars %-sugars have the same con)guration as C7glyceraldehyde at have the same con)guration as C7glyceraldehyde at
the farthest chirality center the farthest chirality center

9-sugars 9-sugars have the same con)guration as -7glyceraldehyde at have the same con)guration as -7glyceraldehyde at
the farthest chirality center the farthest chirality center

naturally occuring monosaccharides belong to the % naturally occuring monosaccharides belong to the %
confgurational family (except for 9-fucose) confgurational family (except for 9-fucose)
4arbohydrates 4arbohydrates

?onosaccharides con)gurational families: ?onosaccharides con)gurational families:

for a compound with for a compound with n n chirality carbons there are ' chirality carbons there are '
n n
possible possible
optical isomers: optical isomers:

' aldotrioses $ pair of enantiomers #CI-7glyceraldehyde( ' aldotrioses $ pair of enantiomers #CI-7glyceraldehyde(

= aldotetroses ' pairs of enantiomers = aldotetroses ' pairs of enantiomers

% aldopentoses = pairs of enantiomers % aldopentoses = pairs of enantiomers

$6 aldohe,oses % pairs of enantiomers $6 aldohe,oses % pairs of enantiomers

half of these compounds belong to the % confgurational family" half of these compounds belong to the % confgurational family"
while the other half belong to the 9 confgurational family while the other half belong to the 9 confgurational family

all the chiral carbons of a C7sugar have the e,act opposite all the chiral carbons of a C7sugar have the e,act opposite
con)guration in the corresponding -7sugar con)guration in the corresponding -7sugar
4arbohydrates 4arbohydrates

4arbohydrates 4arbohydrates

4arbohydrates 4arbohydrates

?onosaccharides: ?onosaccharides:

humans need % monosaccharides and derivatives: humans need % monosaccharides and derivatives:

2 aldohe,oses C7glucose, C7galactose, C7mannose 2 aldohe,oses C7glucose, C7galactose, C7mannose

$ aldopentose C7,ylose $ aldopentose C7,ylose

$ deo,y sugar -7fucose #the only -7sugar( $ deo,y sugar -7fucose #the only -7sugar(

' amino sugars ' amino sugars - -7acetylglucosamine and 7acetylglucosamine and - -7 7
acetylgalactosamine acetylgalactosamine

- -7acetylneuraminic acid precursor of sialic acids 7acetylneuraminic acid precursor of sialic acids

sources for the % monosaccharides: sources for the % monosaccharides:

diet diet

synthesis from C7glucose synthesis from C7glucose


4arbohydrates 4arbohydrates

4arbohydrates 4arbohydrates

?onosaccharides CI- versus #4(I#7(: ?onosaccharides CI- versus #4(I#7(:

%:9 is 7ust a convention and %:9 are 7ust %:9 is 7ust a convention and %:9 are 7ust descriptors descriptors used to used to
describe the confguration of a chiral carbon atom relative to describe the confguration of a chiral carbon atom relative to
the confguration of the chiral carbon atom from the confguration of the chiral carbon atom from
glyceraldehyde glyceraldehyde

optical rotation, melting and boiling points are physical optical rotation, melting and boiling points are physical
properties properties

rotation of the plane7polarized light: rotation of the plane7polarized light:

clockwise direction de,trorotatory compound #4( clockwise direction de,trorotatory compound #4(

counterclockwise direction levorotatory compound #7( counterclockwise direction levorotatory compound #7(

e,amples from carbohydrates: e,amples from carbohydrates:

C7glucose de,trorotatory C7glucose de,trorotatory

C7fructose levorotatory C7fructose levorotatory

C7glyceraldehyd de,trorotatory C7glyceraldehyd de,trorotatory


4arbohydrates 4arbohydrates

?onosaccharides con)gurations: ?onosaccharides con)gurations:

alcohols react with carbonyl compounds #nucleophilic alcohols react with carbonyl compounds #nucleophilic
addition( giving: addition( giving:

hemiacetals: hemiacetals:

alcohol 4 aldehyde alcohol 4 aldehyde

hemi hemiket ketals: als:

alcohol 4 alcohol 4 ket ketone one

=7hydro,y and 07hydro,y aldehydesIketones e,ist mainly in =7hydro,y and 07hydro,y aldehydesIketones e,ist mainly in
the cyclic form of hemiacetalsIhemiketals #intramolecular the cyclic form of hemiacetalsIhemiketals #intramolecular
nucleophilic addition( nucleophilic addition(
4arbohydrates 4arbohydrates

?onosaccharides con)gurations: ?onosaccharides con)gurations:

there are two types of cyclic forms: there are two types of cyclic forms:

pyranoses pyranoses: :

contain a si,7membered ring with an @ atom contain a si,7membered ring with an @ atom

speci)c for aldohe,oses speci)c for aldohe,oses

furanoses furanoses: :

contain a )ve7membered ring with an @ atom contain a )ve7membered ring with an @ atom

speci)c for aldopentoses and ketohe,oses speci)c for aldopentoses and ketohe,oses

the cyclization has the following conse+uences: the cyclization has the following conse+uences:

apparition of a new chiral carbon apparition of a new chiral carbon the anomeric carbon the anomeric carbon

apparition of a new 7@: group apparition of a new 7@: group the glycosidic hydroxyl the glycosidic hydroxyl
4arbohydrates 4arbohydrates

?onosaccharides con)gurations: ?onosaccharides con)gurations:

the con)gurations of the new chiral carbon atom #anomeric the con)gurations of the new chiral carbon atom #anomeric
carbon(: carbon(:

; ; anomer anomer: :

the glycosidic hydro,yl is drawn down the glycosidic hydro,yl is drawn down

the glycosidic hydro,yl and the 79: the glycosidic hydro,yl and the 79:
' '
@: are in @: are in trans trans

in the case of C7glucose the correct name is in the case of C7glucose the correct name is ; ;-%-glucopyranose -%-glucopyranose

< < anomer anomer: :

the glycosidic hydro,yl is drawn up the glycosidic hydro,yl is drawn up

the glycosidic hydro,yl and the 79: the glycosidic hydro,yl and the 79:
' '
@: are in @: are in cis cis

in the case of C7glucose the correct name is in the case of C7glucose the correct name is < <-%-glucopyranose -%-glucopyranose
4arbohydrates 4arbohydrates

?onosaccharides con)gurations: ?onosaccharides con)gurations:

the case of C7ribose #aldopentose(: the case of C7ribose #aldopentose(:

the case of C7fructose #ketohe,ose(: the case of C7fructose #ketohe,ose(:


4arbohydrates 4arbohydrates

?onosaccharides mutarotation: ?onosaccharides mutarotation:

in solution the open7chain form of C7glucose is in e+uilibrium in solution the open7chain form of C7glucose is in e+uilibrium
with the two pyranose formes: with the two pyranose formes:

open7chain form traces open7chain form traces

U U7C7glucopyranose 23D 7C7glucopyranose 23D

V V7C7glucopyranose 62D 7C7glucopyranose 62D

the phenomena of the phenomena of 1.+*'/+*+I/- 1.+*'/+*+I/-: :

when crystals of pure when crystals of pure ; ;-%-glucopyranose -%-glucopyranose are dissolved in water, are dissolved in water,
the speci)c rotation decreases from the speci)c rotation decreases from = >>?#? = >>?#?@ @ to = A?#B to = A?#B@ @

when crystals of pure when crystals of pure < <-%-glucopyranose -%-glucopyranose are dissolved in water, are dissolved in water,
the speci)c rotation increases from the speci)c rotation increases from = >C#B = >C#B@ @ to = A?#B to = A?#B@ @

this phenomena is the conse+uence of the e+uilibrium this phenomena is the conse+uence of the e+uilibrium
established between the two anomeric forms through the established between the two anomeric forms through the
open7chain form open7chain form
4arbohydrates 4arbohydrates

?onosaccharides conformations: ?onosaccharides conformations:

disadvantages of :aworth projections: disadvantages of :aworth projections:

suggest valence angles of $'& suggest valence angles of $'&T T between the carbon atoms between the carbon atoms

suggest valence angles of /& suggest valence angles of /&T T between : and 9 atoms between : and 9 atoms

suggest that the molecules are planar suggest that the molecules are planar

the real 2C structure of carbohydrates molecules are the real 2C structure of carbohydrates molecules are
depicted using conformational representations depicted using conformational representations
4arbohydrates 4arbohydrates
AFHA- AFHA-
59WAT@BHA- 59WAT@BHA-

The glycosidic hydro,yl how we representQ The glycosidic hydro,yl how we representQ

U U anomer: anomer:

:aworth projection down #under the plane of the molecule( :aworth projection down #under the plane of the molecule(

chair conformational representation a,ial chair conformational representation a,ial

V V anomer: anomer:

:aworth projection up #above the plane of the molecule( :aworth projection up #above the plane of the molecule(

chair conformational representation ecuatorial chair conformational representation ecuatorial


4arbohydrates 4arbohydrates

9onformations of C7glucose: 9onformations of C7glucose:

each of the two pyranose anomers e,ist as a mi,ture each of the two pyranose anomers e,ist as a mi,ture
between two conformations: between two conformations:

U U7C7glucopyranose: 7C7glucopyranose:

V V7C7glucopyranose: 7C7glucopyranose:

+), 1/', +*D9, 4/-0/'1,' I +), /-, (I+) *99 +), 1/', +*D9, 4/-0/'1,' I +), /-, (I+) *99
2'/.6 69*4,% I- ,4.*+/'I*9 6/I+I/-5 2'/.6 69*4,% I- ,4.*+/'I*9 6/I+I/-5
4arbohydrates 4arbohydrates

?onosaccharides types of isomers: ?onosaccharides types of isomers:

constitutional isomers: constitutional isomers:

difer in how the atoms are attached one to another difer in how the atoms are attached one to another

stereoisomers: stereoisomers:

atoms are connected in the same manner atoms are connected in the same manner

there are diferences in their spatial arrangement there are diferences in their spatial arrangement

diferent types: diferent types:

enantiomers enantiomers

diastereoisomers diastereoisomers

epimers epimers

anomers anomers
4arbohydrates 4arbohydrates

?onosaccharides types of isomers: ?onosaccharides types of isomers:

enantiomers enantiomers: :

are in relation of object mirror image are in relation of object mirror image

the two enantiomers can not be superimposed through the two enantiomers can not be superimposed through
operations of rotation and translation in the same plan operations of rotation and translation in the same plan

diastereoisomers diastereoisomers: :

stereoisomers that are not in relation of object mirror image stereoisomers that are not in relation of object mirror image

epimers epimers: :

diastereoisomers that difer in the con)guration at one chiral diastereoisomers that difer in the con)guration at one chiral
carbon carbon

anomers anomers: :

diastereoisomers that difer in the con)guration at the diastereoisomers that difer in the con)guration at the
anomeric carbon anomeric carbon
4arbohydrates 4arbohydrates

4arbohydrates 4arbohydrates
58A8TH@?5B< 58A8TH@?5B<
CHA<T5B5@H<@?5B< CHA<T5B5@H<@?5B<

?onosaccharides biochemically relevant reactions: ?onosaccharides biochemically relevant reactions:

oxidation of the hydroxyl group at 4 oxidation of the hydroxyl group at 4


E E
(primary alcohol group) (primary alcohol group): :

takes place under the action of speci)c enzymes takes place under the action of speci)c enzymes

give rise to uronic acids: give rise to uronic acids:

C7glucose C7glucuronic acid C7glucose C7glucuronic acid

C7galactose C7galacturonic acid C7galactose C7galacturonic acid

C7mannose C7mannuronic acid C7mannose C7mannuronic acid

biochemical importance of uronic acids: biochemical importance of uronic acids:

components of glycosaminoglycans: components of glycosaminoglycans:

C7glucuronic acid C7glucuronic acid

-7iduronic acid -7iduronic acid

C7glucuronic acid as a conjugation agent: C7glucuronic acid as a conjugation agent:

glucuronidation catalyzed by glucuronidation catalyzed by 29.4.'/-/89 +'*-0,'*, 29.4.'/-/89 +'*-0,'*,

increases the solubility of diferent endo7 and e,ogene compounds increases the solubility of diferent endo7 and e,ogene compounds

the conjugated compunds can be e,creted through urine and feces the conjugated compunds can be e,creted through urine and feces
4arbohydrates 4arbohydrates

<ynthesis and utilization of C7glucuronic acid: <ynthesis and utilization of C7glucuronic acid:

synthesis is a two step process synthesis is a two step process: :

conversion of C7glucose7$7phosphate to WC. conversion of C7glucose7$7phosphate to WC.K Kglucose glucose

o,idation of WC. o,idation of WC.K Kglucose to WC. glucose to WC.K Kglucuronate glucuronate

observation: observation:

WC. WC.K Kglucose metabolically active form of C7glucose glucose metabolically active form of C7glucose

WC. WC.K Kglucuronate metabolically active form of C7glucuronic acid glucuronate metabolically active form of C7glucuronic acid

utilization of %-glucuronic acid utilization of %-glucuronic acid: :

WC. WC.K Kglucuronate is substrate for glucuronosyl transferases glucuronate is substrate for glucuronosyl transferases

used to conjugate: used to conjugate:

endogenous compounds: bilirubin, steroid hormones endogenous compounds: bilirubin, steroid hormones

e,ogenous compounds: drugs e,ogenous compounds: drugs


4arbohydrates 4arbohydrates

Bilirubin neonates and icterus: Bilirubin neonates and icterus:

s s
4arbohydrates 4arbohydrates

4arbohydrates 4arbohydrates

4arbohydrates 4arbohydrates

?onosaccharides biochemically relevant reactions: ?onosaccharides biochemically relevant reactions:

reduction reduction: :

chemically reduction chemically reduction: :

reductive agent is 8aB: reductive agent is 8aB:


= =

enzymatically reduction enzymatically reduction: :

reductive agent is 8AC.: reductive agent is 8AC.:

process catalyzed by process catalyzed by ',%.4+*, ',%.4+*,

gives rise to polyhydro,y alcohols #polyols(: gives rise to polyhydro,y alcohols #polyols(:

C7glucose C7glucitol #C7sorbitol( C7glucose C7glucitol #C7sorbitol(

C7mannose C7mannitol C7mannose C7mannitol

C7fructose C7mannitol 4 C7sorbitol C7fructose C7mannitol 4 C7sorbitol


4arbohydrates 4arbohydrates

Biochemically relevant polyols: Biochemically relevant polyols:

%-ribitol %-ribitol: :

produced from C7ribose produced from C7ribose

component of the vitamin B component of the vitamin B


' '
#ribo>avin( #ribo>avin(

%-sorbitol %-sorbitol: :

produced from C7glucose and C7fructose produced from C7glucose and C7fructose

present in fruits and berries present in fruits and berries

used as a sweetener used as a sweetener

%-xylitol %-xylitol: :

produced from C7,ylose produced from C7,ylose

used as a sweetener in *sugarless* gum and candies used as a sweetener in *sugarless* gum and candies

glycerol glycerol: :

component of acylglycerols #mono7, di7, triacylglycerol( component of acylglycerols #mono7, di7, triacylglycerol(

myo-inositol myo-inositol: :

component of some glycerophospholipids component of some glycerophospholipids


4arbohydrates 4arbohydrates

?onosaccharides biochemically relevant reactions: ?onosaccharides biochemically relevant reactions:

esterifcation with Fphosphoric acidF (phosphorylation) esterifcation with Fphosphoric acidF (phosphorylation): :

gives rise to phosphoric esters gives rise to phosphoric esters

the process is catalyzed by 1H8A<5<: the process is catalyzed by 1H8A<5<:

posphoric esters are metabolic intermediates posphoric esters are metabolic intermediates
4arbohydrates 4arbohydrates

?onosaccharides derivatives deo,y sugars: ?onosaccharides derivatives deo,y sugars:

one 7@: group is replaced by 7: one 7@: group is replaced by 7:

biologically relevant deo,y sugars: biologically relevant deo,y sugars:

?-deoxy-%-ribose ?-deoxy-%-ribose: :

e,ists as a furanose form #'7deo,y7 e,ists as a furanose form #'7deo,y7V V7C7ribofuranose( 7C7ribofuranose(

component of C8A component of C8A

9-fucose 9-fucose: :

67deo,y7 67deo,y7U U7 7C7galactopyranose C7galactopyranose

component of diferent glycoproteins #see the AB@ blood groups component of diferent glycoproteins #see the AB@ blood groups
system( system(
4arbohydrates 4arbohydrates

?onosaccharides derivatives amino sugars: ?onosaccharides derivatives amino sugars:

one 7@: group is replaced by an 78: one 7@: group is replaced by an 78:
' '
group group

usually the 78: usually the 78:


' '
group is acetylated group is acetylated

biologically relevant amino sugars: biologically relevant amino sugars:

%-glucosamine %-glucosamine: :

e,ists in pyranose form #'7amino7'7deo,y7 e,ists in pyranose form #'7amino7'7deo,y7U UI IV V7C7glucopyranose( 7C7glucopyranose(

%-galactosamine %-galactosamine: :

e,ists in pyranose form #'7amino7'7deo,y7 e,ists in pyranose form #'7amino7'7deo,y7U UI IV V7C7galactopyranose( 7C7galactopyranose(

%-mannosamine %-mannosamine: :

component of the neuraminic acid component of the neuraminic acid

the acylated derivatives of neuraminic acids are called the acylated derivatives of neuraminic acids are called sialic acids sialic acids

present in glycosaminoglycans and glycoproteins present in glycosaminoglycans and glycoproteins


4arbohydrates 4arbohydrates

4arbohydrates 4arbohydrates

?onosaccharides derivatives glycosides: ?onosaccharides derivatives glycosides:

treatment of a monosaccharide with an alcohol #9: treatment of a monosaccharide with an alcohol #9:
2 2
@:( in @:( in
acid catalysis #:9l( gives rise to glycosides acid catalysis #:9l( gives rise to glycosides

naming glycosides: naming glycosides:

the name of the aglycone the name of the aglycone

replace the suS, X7ose* with X7oside* replace the suS, X7ose* with X7oside*

properties of the glycosides: properties of the glycosides:

do not e,hibit mutarotation do not e,hibit mutarotation

undergo hydrolysis in acid catalysis undergo hydrolysis in acid catalysis

biologically relevant glycosides: biologically relevant glycosides:

nucleosides: ribonucleosides #B8A(, deo,yribonucleosides #C8A( nucleosides: ribonucleosides #B8A(, deo,yribonucleosides #C8A(

cardiotonic glycosides: digo,in #from fo,glove, cardiotonic glycosides: digo,in #from fo,glove, %igitalis lanata %igitalis lanata( (
4arbohydrates 4arbohydrates

4arbohydrates 4arbohydrates

Cisaccharides: Cisaccharides:

compounds that contain two monosaccharide units bonded compounds that contain two monosaccharide units bonded
through an acetal linkage between: through an acetal linkage between:

glycosidic hydro,yl of one unit glycosidic hydro,yl of one unit

any hydro,yl of the second unit any hydro,yl of the second unit

classi)cation of disaccharides: classi)cation of disaccharides:

based on the chemical composition: based on the chemical composition:

disaccharides containing two identical units #maltose, isomaltose, disaccharides containing two identical units #maltose, isomaltose,
trehalose( trehalose(

disaccharides containing two diferent units #lactose, sucrose( disaccharides containing two diferent units #lactose, sucrose(

based on their reducing properties: based on their reducing properties:

reducing disaccharides: maltose, isomaltose, lactose reducing disaccharides: maltose, isomaltose, lactose, cellobiose , cellobiose

non7reducing disaccharides: trehalose, sucrose non7reducing disaccharides: trehalose, sucrose


4arbohydrates 4arbohydrates

:ow to make the systematic name of disaccharidesQ :ow to make the systematic name of disaccharidesQ

we must specify the following informations: we must specify the following informations:

the atoms involved in the glycosidic bond the atoms involved in the glycosidic bond

$7= $7=L #the most fre+uent( L #the most fre+uent(

$76L #less fre+uent( $76L #less fre+uent(

$7$L #e,tremely rare( $7$L #e,tremely rare(

the con)guration of the glycosidic bond the con)guration of the glycosidic bond # #U UI IV V( (

the names of the two monosaccharides the names of the two monosaccharides

the ring type: the ring type:

pyranose pyranose

furanose furanose

maltose: maltose:

=7 =7/ /7# 7#U U7C7glucoryranosyl(7C7glucopyran 7C7glucoryranosyl(7C7glucopyranose ose

U U7C7glucopyranosyl7#$7=(7C7glucopyran 7C7glucopyranosyl7#$7=(7C7glucopyranose ose


4arbohydrates 4arbohydrates

?altose: ?altose:

released during the hydrolysis of starch released during the hydrolysis of starch

present in malt, germinated grains #barley( present in malt, germinated grains #barley(

it is a reducing disaccharide e,hibits mutarotation it is a reducing disaccharide e,hibits mutarotation


9ellobiose: 9ellobiose:

released during the hydrolysis of cellulose released during the hydrolysis of cellulose

it is a reducing disaccharide e,hibits mutarotation it is a reducing disaccharide e,hibits mutarotation

systematic names: systematic names:

Y Y

Y Y
4arbohydrates 4arbohydrates

-actose: -actose:

the major carbohydrate in milk the major carbohydrate in milk

it contains: C7galactose 4 C7glucose it contains: C7galactose 4 C7glucose

it is a reducing disaccharide e,hibits mutarotation it is a reducing disaccharide e,hibits mutarotation

systematic names: systematic names:

Y Y

Y Y

metabolism in humans: metabolism in humans:

synthesized in the mammary gland during lactation period synthesized in the mammary gland during lactation period

it is hydrolyzed in the lumen of small intestine by it is hydrolyzed in the lumen of small intestine by 9*4+*, 9*4+*,: :

-A9TA<5 P -A9TA<5 P V V7C7galactosidase 7C7galactosidase

lactase levels decrease at about the age of 073 years #milk is no lactase levels decrease at about the age of 073 years #milk is no
longer the major source of nourishment( longer the major source of nourishment(

lactase levels do not decrease 8orthern 5uropean populations lactase levels do not decrease 8orthern 5uropean populations
#Canes 2D lactase deScient, Thais /3D lactase deScient( #Canes 2D lactase deScient, Thais /3D lactase deScient(
4arbohydrates 4arbohydrates

-actose intolerance: -actose intolerance:

primary lactose intolerance: primary lactose intolerance:

due to the lack of the enzyme due to the lack of the enzyme

secondary lactose intolerance: secondary lactose intolerance:

due to the loss of the enzyme as a conse+uence of some due to the loss of the enzyme as a conse+uence of some
pathological conditions afecting the small intestine pathological conditions afecting the small intestine

conse+uences: conse+uences:

lactose is converted in the colon through bacterial lactose is converted in the colon through bacterial
fermentation into 9@ fermentation into 9@
' '
, : , :
' '
, 9: , 9:
= =
and diferent organic acids and diferent organic acids

diarrhea, >atulence, pain diarrhea, >atulence, pain

therapeutic approaches: therapeutic approaches:

consumption of lactose7free milk and fermented products consumption of lactose7free milk and fermented products
#yogurt, aged cheeses( #yogurt, aged cheeses(

consumption of tablets that contain the lactase enzyme consumption of tablets that contain the lactase enzyme
4arbohydrates 4arbohydrates

<ucrose: <ucrose:

the most abundant disaccharide found in nature the most abundant disaccharide found in nature

synthesized only by plants #sugar cane( synthesized only by plants #sugar cane(

it contains: C7glucose 4 C7fructose it contains: C7glucose 4 C7fructose

it is a non7reducing disaccharide does not e,hibit it is a non7reducing disaccharide does not e,hibit
mutarotation mutarotation

systematic names: systematic names:

Y Y

Y Y

sucrose hydrolysis: sucrose hydrolysis:

catalyzed by catalyzed by I-G,'+*, I-G,'+*,

the e+uimolar mi,ture of C7glucose and C7fructose has the the e+uimolar mi,ture of C7glucose and C7fructose has the
following characteristics: following characteristics:

is levorotatory #7 ''E& is levorotatory #7 ''E&T( #sucrose is de,trorotatory 4 66E0T( T( #sucrose is de,trorotatory 4 66E0T(

is sweeter than sucrose #due to C7fructose( is sweeter than sucrose #due to C7fructose(
4arbohydrates 4arbohydrates

The taste a matter of chemistry and biochemistry: The taste a matter of chemistry and biochemistry:

the the sensation of sensation of taste: taste:

is the conse+uence of the binding of a molecule to a speci)c is the conse+uence of the binding of a molecule to a speci)c
receptor located in taste buds receptor located in taste buds

the the *taste* sensation is formed in the brain *taste* sensation is formed in the brain

the sense of taste has two major functions: the sense of taste has two major functions:

rejection of undesirable #even lethal( foods rejection of undesirable #even lethal( foods

selection of the foods according to the needs of a person selection of the foods according to the needs of a person

there are 0 primary sensations of taste: there are 0 primary sensations of taste:

sour taste caused by acids sour taste caused by acids

salty taste caused by salts salty taste caused by salts

sweet taste caused by many diferent substances sweet taste caused by many diferent substances

bitter taste caused by alkaloids bitter taste caused by alkaloids

umami #japanese, umami #japanese, delicious delicious( taste caused by -7glutamate ( taste caused by -7glutamate
containing foods containing foods
4arbohydrates 4arbohydrates

4arbohydrates 4arbohydrates

<ynthetic sweeteners: <ynthetic sweeteners:

noncarbohydrate molecules that mimic the taste of sucrose noncarbohydrate molecules that mimic the taste of sucrose

saccharin: saccharin:

the )rst synthetic sweetener the )rst synthetic sweetener

it is not metabolized by the human body has no caloric value it is not metabolized by the human body has no caloric value

aspartame: aspartame:

aspartylphenylalanine methyl ester aspartylphenylalanine methyl ester

it is hydrolyzed in the small intestine it is hydrolyzed in the small intestine

has a caloric value due to the two amino acids has a caloric value due to the two amino acids

it is forbiden for people with .:58R-15T@8WBHA #inability to it is forbiden for people with .:58R-15T@8WBHA #inability to
metabolize phenylalanine( metabolize phenylalanine(
4arbohydrates 4arbohydrates

.olysaccharides: .olysaccharides:

contain contain O $& monosaccharide or derivatives units O $& monosaccharide or derivatives units

classi)cation: classi)cation:

according to chemical composition: according to chemical composition:

homopolysaccharides #homoglycans( starch, glycogen, cellulose, homopolysaccharides #homoglycans( starch, glycogen, cellulose,
chitin chitin

heteropolysaccharides #heteroglycans( glycosaminoglycans heteropolysaccharides #heteroglycans( glycosaminoglycans

according to biological function: according to biological function:

storage polysaccharides starch, glycogen storage polysaccharides starch, glycogen

structural polysaccharides cellulose, chitin structural polysaccharides cellulose, chitin


4arbohydrates 4arbohydrates

<tarch: <tarch:

storage polysaccharide in plants storage polysaccharide in plants

particles of 27$&& particles of 27$&& J Jm found in the cytoplasma of the vegetal m found in the cytoplasma of the vegetal
cells: cells:

amylose amylose: :

about '&D of the particle about '&D of the particleLs mass Ls mass

unbranched polymer # unbranched polymer #contains contains $&& $&&& C7glucose residues( $&& $&&& C7glucose residues(

the units are linked through the units are linked through U U $7= glycosidic bonds $7= glycosidic bonds

has a conformation of a left7handed heli, has a conformation of a left7handed heli,

amylopectin amylopectin: :

about %&D of the particleLs mass about %&D of the particleLs mass

branched polymer #contains up to $& branched polymer #contains up to $&


6 6
C7glucose residues( C7glucose residues(

the units are linked through: the units are linked through:

U U $7= glycosidic bonds $7= glycosidic bonds

U U $76 glycosidic bonds branching points $76 glycosidic bonds branching points

has @85 B5CW9H8M 58C and ?A8R 8@87B5CW9H8M 58C< has @85 B5CW9H8M 58C and ?A8R 8@87B5CW9H8M 58C<
4arbohydrates 4arbohydrates

4arbohydrates 4arbohydrates

Mlycogen: Mlycogen:

storage polysaccharide in animals and fungi storage polysaccharide in animals and fungi

has a structure very similar to that of amylopectin: has a structure very similar to that of amylopectin:

the C7glucose units are linked through: the C7glucose units are linked through:

U U $7= glycosidic bonds $7= glycosidic bonds

U U $76 glycosidic bonds branching points $76 glycosidic bonds branching points

fre+uency of rami)cations: fre+uency of rami)cations:

amylopectin '= 2& C7glucose residues amylopectin '= 2& C7glucose residues

glycogen $& C7glucose residues glycogen $& C7glucose residues

glycogen has: glycogen has:

/-, ',%.4I-2 ,-% /-, ',%.4I-2 ,-%

1*-8 -/--',%.4I-2 ,-% 1*-8 -/--',%.4I-2 ,-% all the enzymes involved in the all the enzymes involved in the
degradation of glycogen and glycogen synthesis act at these ends degradation of glycogen and glycogen synthesis act at these ends
in order to ensure a fast metabolisation rate in order to ensure a fast metabolisation rate
4arbohydrates 4arbohydrates

9ellulose: 9ellulose:

structural polysaccharide in plants structural polysaccharide in plants

linear polymer: linear polymer:

contains up to $0&&& C7glucose units contains up to $0&&& C7glucose units

the units are linked through the units are linked through V V $7= glycosidic bonds $7= glycosidic bonds

structural features: structural features:

each C7glucose unit is rotated $%& each C7glucose unit is rotated $%&T relative to its neighbors T relative to its neighbors

there are two types of hydrogen bonds in cellulose: there are two types of hydrogen bonds in cellulose:

intrachain bonds intrachain bonds between the 7@: group from 9 between the 7@: group from 9
2 2
and the @ ring of and the @ ring of
the ne,t residue the ne,t residue

interchain bonds interchain bonds between @'7:Y@6 and @67:Y@2 between @'7:Y@6 and @67:Y@2

due to the intra7 and interchain hydrogen bonds, cellulose is due to the intra7 and interchain hydrogen bonds, cellulose is
water insoluble despite its hydrophilicity water insoluble despite its hydrophilicity
4arbohydrates 4arbohydrates

4arbohydrates 4arbohydrates

9ellulose: 9ellulose:

the the V V $7= glycosidic bonds of cellulose are hydrolyzed by $7= glycosidic bonds of cellulose are hydrolyzed by
4,99.9*, 4,99.9*,: :

V V7glucosidases 7glucosidases

humans do not produce these enzymes humans can not digest humans do not produce these enzymes humans can not digest
cellulose #alimentary )ber( cellulose #alimentary )ber(

are produced by: are produced by:

bacteria found in the rumen of ruminants #cows, sheep( bacteria found in the rumen of ruminants #cows, sheep(

bacteria found in the digestive tract of termits bacteria found in the digestive tract of termits

plant cell walls contain: plant cell walls contain:

cellulose )bers cellulose )bers

other polysaccharides other polysaccharides

lignins lignins

diferent proteins diferent proteins


4arbohydrates 4arbohydrates

9hitin: 9hitin:

structural polysaccharide found in the e,oscheleton of structural polysaccharide found in the e,oscheleton of
invertebrates #crustaceans, insects, spiders( invertebrates #crustaceans, insects, spiders(

structural features: structural features:

the unit is the unit is - -7acetyl7C7glucosamine 7acetyl7C7glucosamine

each unit is rotated with $%& each unit is rotated with $%&T relative to its neighbors T relative to its neighbors

the units are linked through the units are linked through V V $7= glycosidic bonds $7= glycosidic bonds

it has a similar structure with that of cellulose it has a similar structure with that of cellulose
4arbohydrates 4arbohydrates

9hitosan: 9hitosan:

results through alkaline hydrolysis of chitin results through alkaline hydrolysis of chitin

structural features: structural features:

the unit is C7glucosamine the unit is C7glucosamine

the units are linked through the units are linked through V V $7= glycosidic bonds $7= glycosidic bonds

applications: applications:

agriculture #biopesticed( agriculture #biopesticed(

food industry to protect the fruits food industry to protect the fruits

medicine: medicine:

antibacterial agent antibacterial agent

for the treatment of wounds for the treatment of wounds

drug carrier drug carrier


4arbohydrates 4arbohydrates

Mlycosaminoglycans: Mlycosaminoglycans:

unbranched heteropolysaccharides unbranched heteropolysaccharides

structural features: structural features:

the unit is a disaccharide containing: the unit is a disaccharide containing:

uronic acid: C7glucuronic, -7iduronic uronic acid: C7glucuronic, -7iduronic

amino sugar: C7glucosamine, C7galactosamine amino sugar: C7glucosamine, C7galactosamine

several types of glycosidic bonds: several types of glycosidic bonds:

V V $72 $72

V V $7= $7=

the amino7 and hydro,yl7 groups can be modi)ed through: the amino7 and hydro,yl7 groups can be modi)ed through:

acetylation acetylation

sulfatation sulfatation

the presence of uronic acids and sulfate groups the presence of uronic acids and sulfate groups
glycosaminoglycans have many anionic charges (polyanionic) glycosaminoglycans have many anionic charges (polyanionic)
4arbohydrates 4arbohydrates

4arbohydrates 4arbohydrates

:yaluronic acid: :yaluronic acid:

s structural features: tructural features:

one disaccharide unit contains: one disaccharide unit contains:

C7glucuronic acid C7glucuronic acid

- -7acetyl7C7glucosamine 7acetyl7C7glucosamine

the two sugars are bonded through a the two sugars are bonded through a V V $72 glycosidic bond $72 glycosidic bond

the consecutive disaccharide units are bonded through a the consecutive disaccharide units are bonded through a V V $7= $7=
glycosidic bond glycosidic bond

contains '0& '0&&& disaccharide units contains '0& '0&&& disaccharide units

it is an e,tended, left7handed heli, that binds cations #1 it is an e,tended, left7handed heli, that binds cations #1
4 4
, 8a , 8a
4 4
, ,
9a 9a
'4 '4
( (
4arbohydrates 4arbohydrates

:yaluronic acid: :yaluronic acid:

characteristics: characteristics:

it is the only glycosaminoglycan: it is the only glycosaminoglycan:

which is not sulfated which is not sulfated

which is not covalently linked to proteins which is not covalently linked to proteins

physical properties: physical properties:

hyaluronate solutions have hyaluronate solutions have GI4/,9*+I4 6'/6,'+I, GI4/,9*+I4 6'/6,'+I,: :

low shear stress the >ow is blocked low shear stress the >ow is blocked

high shear stress the molecules >ow #diminished resistance( high shear stress the molecules >ow #diminished resistance(

biological functions: biological functions:

major component of the connective tissues, synovial >uid act major component of the connective tissues, synovial >uid act
as biological absorber and lubricant as biological absorber and lubricant

major component of the vitreous humor of the eye major component of the vitreous humor of the eye
4arbohydrates 4arbohydrates

Mlycoconjugates: Mlycoconjugates:

comple, molecules that contain: comple, molecules that contain:

peptidesIproteins peptidesIproteins

polysaccharides covalently linked to the peptidesIproteins polysaccharides covalently linked to the peptidesIproteins

the sugar content vary between $7/&D of the weight the sugar content vary between $7/&D of the weight

many diverse biological functions: many diverse biological functions:

enzymes enzymes

hormones hormones

antibodies antibodies

structural function structural function

three main classes: three main classes:

proteoglycans proteoglycans

peptidoglycans peptidoglycans

glycoproteins glycoproteins
4arbohydrates 4arbohydrates

.roteoglycans: .roteoglycans:

components of the e,tracellular matri, of tissues components of the e,tracellular matri, of tissues

structural features: structural features:

core protein core protein

multiple oligosaccharides: multiple oligosaccharides:

- -7linked through an Asn residue 7linked through an Asn residue

/ /7linked through a <er residue 7linked through a <er residue

multiple chains of glycosaminoglycans: multiple chains of glycosaminoglycans:

/ /7linked through diferent small oligosaccharides 7linked through diferent small oligosaccharides

many proteoglycans associate non-covalently with a many proteoglycans associate non-covalently with a
hyaluronic acid macromolecule giving rise to bottle-brush hyaluronic acid macromolecule giving rise to bottle-brush
aggregates aggregates
4arbohydrates 4arbohydrates

4arbohydrates 4arbohydrates
9@B5 .B@T5H8 9@B5 .B@T5H8

.eptidoglycans: .eptidoglycans:

components of the bacterial cell wall components of the bacterial cell wall

structural features: structural features:

heteroglycan component heteroglycan component: :

- -7acetyl7C7glucosamine #8AM( 7acetyl7C7glucosamine #8AM(

- -7acetylmuramic acid #8A?( 7acetylmuramic acid #8A?(

8AM and 8A? are linked through a 8AM and 8A? are linked through a V V $7= glycosidic bond $7= glycosidic bond

peptide component peptide component: :

the tetrapeptide -7Ala C7Hsoglu -7-ys C7Ala the tetrapeptide -7Ala C7Hsoglu -7-ys C7Ala

each 8A? residue is covalently linked to one tetrapeptide each 8A? residue is covalently linked to one tetrapeptide

cross7linking of tetrapeptides: cross7linking of tetrapeptides:

is made through pentaglycine bridges is made through pentaglycine bridges

links a -7-ys residue from a tetrapeptide with the C7Ala residue links a -7-ys residue from a tetrapeptide with the C7Ala residue
from a neighbor tetrapeptide from a neighbor tetrapeptide
4arbohydrates 4arbohydrates

4arbohydrates 4arbohydrates

Hnhibition of peptidoglycan biosynthesis: Hnhibition of peptidoglycan biosynthesis:

the cell wall: the cell wall:

its synthesis in blocked by its synthesis in blocked by 6,-I4I99I- 6,-I4I99I-

.enicillin M: .enicillin M:

$/'% <ir Ale,ander leming observed that the mold $/'% <ir Ale,ander leming observed that the mold 6enicillium 6enicillium
notatum notatum which contaminated a bacterial culture lysed the bacteria which contaminated a bacterial culture lysed the bacteria
the mold produces an the mold produces an antibiotic substance antibiotic substance

$/2% the antibiotic substance was isolated by :oward lorey and $/2% the antibiotic substance was isolated by :oward lorey and
5rnest 9hain as .enicillin M 5rnest 9hain as .enicillin M

$/== .enicillin M available for the use of civilian population $/== .enicillin M available for the use of civilian population

mechanism of action of .enicillins: mechanism of action of .enicillins:

the the < <7lactam ring is higly reactive 7lactam ring is higly reactive

acylate a hydro,yl group of the enzyme involved in the acylate a hydro,yl group of the enzyme involved in the
transpeptidation #step re+uired for the cell wall synthesis( transpeptidation #step re+uired for the cell wall synthesis(
+he cell +he cell

.enicillinases: .enicillinases:

some bacteria produce some bacteria produce 6,-I4I99I-*, 6,-I4I99I-*,: :

these enzymes hydrolyzes the these enzymes hydrolyzes the < <7lactam ring to produce 7lactam ring to produce
penicillinoic acids penicillinoic acids

these enzymes confer resistance to .enicillins these enzymes confer resistance to .enicillins
+he cell +he cell

Mlycoproteins: Mlycoproteins:

structural features: structural features:

the carbohydrate chains vary in lengh #$ 2& the carbohydrate chains vary in lengh #$ 2&
monosaccharides( monosaccharides(

the carbohydrate chains are branched the carbohydrate chains are branched

there are two types of covalent links to the polypeptide chain: there are two types of covalent links to the polypeptide chain:

/ /7linked oligosaccharides through <erIThr residues 7linked oligosaccharides through <erIThr residues

- -7linked oligosaccharides through Asn residues 7linked oligosaccharides through Asn residues

enormous structural diversity of the oligosaccharide chains of enormous structural diversity of the oligosaccharide chains of
the same glycoprotein: the same glycoprotein:

combination of diferent monosaccharides #C7Mlc, C7Mal, C7?an, C7 combination of diferent monosaccharides #C7Mlc, C7Mal, C7?an, C7
Fyl, amino sugars( Fyl, amino sugars(

two types of glycosidic bonds: two types of glycosidic bonds: U U or or V V

variability of the glycosidic bonds: 9$ from one sugar and 9', 92, variability of the glycosidic bonds: 9$ from one sugar and 9', 92,
9=, 96 from another sugar 9=, 96 from another sugar
4arbohydrates 4arbohydrates

- -7linked oligosaccharides: 7linked oligosaccharides:

the chain is linked through a residue of Mlc8Ac # the chain is linked through a residue of Mlc8Ac #V V linked( linked(

there are three subclasses: there are three subclasses:

high mannose high mannose

comple, comple,

hybrid hybrid

all have a common core pentasaccharide: Mlc8Ac all have a common core pentasaccharide: Mlc8Ac
' '
?an ?an
2 2
/ /7linked oligosaccharides: 7linked oligosaccharides:

there are several ways to make the link: there are several ways to make the link:

through a residue of Mal8Ac through a residue of Mal8Ac

through the trisacchar: C7Mal C7Mal C7Fyl through the trisacchar: C7Mal C7Mal C7Fyl
4arbohydrates 4arbohydrates

4arbohydrates 4arbohydrates

AB@ blood groups a matter of glycoproteins: AB@ blood groups a matter of glycoproteins:

discovered in $/&$ by 1arl -andsteiner #8obel .rize in discovered in $/&$ by 1arl -andsteiner #8obel .rize in
.hysiology and ?edicine $/2&( .hysiology and ?edicine $/2&(

on the surface of our cells there are diferent on the surface of our cells there are diferent
oligosaccharide: oligosaccharide:

they are components of glycoproteins and glycolipids they are components of glycoproteins and glycolipids

*D/ blood groups antigens *D/ blood groups antigens: :

type * type *: :

A antigens on cells A antigens on cellsL surface L surface

a anti7B antibodies in nti7B antibodies in the the blood blood

type D type D: :

B antigens on cells B antigens on cellsL surface L surface

anti7A antibodies in anti7A antibodies in the the blood blood

type *D type *D: :

A 4 B antigens A 4 B antigens on cellsL surface on cellsL surface

no anti7A and anti7B antibodies no anti7A and anti7B antibodies in the blood in the blood

type / type /: :

no antigens no antigens on cellsL surface on cellsL surface

both anti7A and anti7B antibodies in the blood both anti7A and anti7B antibodies in the blood
4arbohydrates 4arbohydrates

4arbohydrates 4arbohydrates

AB@ blood groups a matter of glycoproteins: AB@ blood groups a matter of glycoproteins:

composition characteristics of the antigens: composition characteristics of the antigens:

type @ persons: type @ persons:

have an inactive glycosyl transferase have an inactive glycosyl transferase

have the : antigen have the : antigen

type A persons: type A persons:

have an active glycosyl transferase which adds Mal8Ac to the : have an active glycosyl transferase which adds Mal8Ac to the :
antigen antigen

type B persons: type B persons:

have an active glycosyl transferase which adds Mal to the : antigen have an active glycosyl transferase which adds Mal to the : antigen

type AB persons: type AB persons:

both glycosyl transferases are active both glycosyl transferases are active

observations: observations:

type AB universal blood acceptor type AB universal blood acceptor

type @ universal blood donor type @ universal blood donor


4arbohydrates 4arbohydrates

-ipids: -ipids:

compounds with a great structural variety which are compounds with a great structural variety which are
de)ned on the basis of a physical property water solubility de)ned on the basis of a physical property water solubility

in respect to their structure lipids are: in respect to their structure lipids are:

hydrophobic water7insoluble hydrophobic water7insoluble

amphipatic can form micelle amphipatic can form micelle

biological functions of lipids: biological functions of lipids:

essential components of the biological membranes essential components of the biological membranes

energy7storage form energy7storage form

thermal insulation and protection of diferent organs thermal insulation and protection of diferent organs

hormones hormones

intracellular messengers intracellular messengers


9ipids 9ipids

9ipids 9ipids

-ipids clasiScation: -ipids clasiScation:

hydrolyzable lipids: hydrolyzable lipids:

non7hydrolyzable lipids: non7hydrolyzable lipids:


9ipids 9ipids

atty acids: atty acids:

fatty acids P monocarbo,ylic acids with long hydrocarbon fatty acids P monocarbo,ylic acids with long hydrocarbon
chain chain #$'7 '& carbon atoms( #$'7 '& carbon atoms(

clasiScation of fatty acids clasiScation of fatty acids: :

saturated fatty acids saturated fatty acids: :

do not have 9P9 bonds do not have 9P9 bonds

unsaturated fatty acids unsaturated fatty acids: :

do have one or more 9P9 bonds with do have one or more 9P9 bonds with 4I 4I con)guration con)guration

the double bonds are separated by methylene groups # the double bonds are separated by methylene groups #the double the double
bonds are not con7ugated bonds are not con7ugated( (

clasiScation: clasiScation:

monounsaturated fatty acids monounsaturated fatty acids

p poly olyu unsaturated nsaturated f fatty atty a acids #.WA( cids #.WA(

the p1 the p1
a a
of the carbo,yl group is =E0 0E& #at physiological p: of the carbo,yl group is =E0 0E& #at physiological p:
fatty acids are ionized( fatty acids are ionized(
9ipids 9ipids


atty acids properties: atty acids properties:

physical properties depend upon: physical properties depend upon:

the length of the hydrocarbon chain the length of the hydrocarbon chain

the degree of unsaturation the degree of unsaturation

saturated fatty acids: saturated fatty acids:

melting points increase with the molecular weight melting points increase with the molecular weight

increases the number of van der !aals interactions increases the number of van der !aals interactions

unsaturated fatty acids: unsaturated fatty acids:

due to the due to the cis cis con)guration of the 9P9 bonds, the molecules con)guration of the 9P9 bonds, the molecules
bend bend

the molecules can not pack very tightly as saturated fatty the molecules can not pack very tightly as saturated fatty
acids acids

melting points decrease as the number of 4H4 bonds increase melting points decrease as the number of 4H4 bonds increase
9ipids 9ipids

atty acids properties: atty acids properties:

detergent properties: detergent properties:

are a conse+uence of the amphipatic molecules of fatty acids: are a conse+uence of the amphipatic molecules of fatty acids:

the hydrocarbon tails interact with hydrophobic compounds #oil( the hydrocarbon tails interact with hydrophobic compounds #oil(

the carbo,ylate group interact with water molecules the carbo,ylate group interact with water molecules

in vivo in vivo free fatty acids can damage cells due to their free fatty acids can damage cells due to their
detergent properties free fatty acids are bind by diferent detergent properties free fatty acids are bind by diferent
proteins: proteins:

blood serum albumin blood serum albumin

intracellular space AB.s # intracellular space AB.s #f fatty atty a acid cid b binding inding
p proteins( roteins(
9ipids 9ipids

atty acid nomenclature: atty acid nomenclature:

common names common names: :

do not ofer informations about the length of the hydrocarbon tail do not ofer informations about the length of the hydrocarbon tail

fre+uently used in biochemistry fre+uently used in biochemistry

e,amples: lauric acid, palmitic acid, arachidonic acid, behenic e,amples: lauric acid, palmitic acid, arachidonic acid, behenic
acid acid

I.6*4 nomenclature I.6*4 nomenclature: :

the carbo,yl carbon is labeled 9 the carbo,yl carbon is labeled 9


$ $

the remaining carbons are numbered conse+uentially the remaining carbons are numbered conse+uentially

unsaturated acids 9P9 bond#s( position#s( is speci)ed by unsaturated acids 9P9 bond#s( position#s( is speci)ed by Z Z
n n
# #n n, ,
carbon atom number( carbon atom number(

I IomegaF nomenclature omegaF nomenclature: :

[ [ designates the carbon atom farthest of the carbo,yl group designates the carbon atom farthest of the carbo,yl group

does not ofer informations about the number of carbon atoms does not ofer informations about the number of carbon atoms
nor the double bonds nor the double bonds

it is another way for unsaturated fatty acids clasiScation it is another way for unsaturated fatty acids clasiScation
9ipids 9ipids

atty acids atty acids [ [ clasiScation system: clasiScation system:

J J K $ fatty acids K $ fatty acids: :

U U7linolenic acid #$%: 7linolenic acid #$%:2 2Z Z


/,$',$0 /,$',$0
( vegetal oils ( vegetal oils

eicosapentaenoic acid #5.A, '&:0 eicosapentaenoic acid #5.A, '&:0Z Z


0,%,$$,$=,$3 0,%,$$,$=,$3
( )sh products ( )sh products

docosahe,aenoic acid #C:A, '':6 docosahe,aenoic acid #C:A, '':6Z Z


=,3,$&,$2,$6,$/ =,3,$&,$2,$6,$/
( )sh products ( )sh products

J J K E fatty acids K E fatty acids: :

arachidonic acid #'&:= arachidonic acid #'&:=Z Z


0,%,$$,$= 0,%,$$,$=
( (

linoleic acid #$%:' linoleic acid #$%:'Z Z


/,$' /,$'
( (

J J K L fatty acids K L fatty acids: :

oleic acid #$%:$ oleic acid #$%:$Z Z


/ /
( (
9ipids 9ipids

atty acids essential fatty acids: atty acids essential fatty acids:

fatty acids that can not be synthesized by the human body fatty acids that can not be synthesized by the human body

humans lack the enzymes that introduce 9P9 bonds humans lack the enzymes that introduce 9P9 bonds
beyond 9 beyond 9
$& $&
# #%,*+.'*, %,*+.'*,( (

they must be supplied through the diet: they must be supplied through the diet:

U U7linolenic acid #$%:2 7linolenic acid #$%:2Z Z


/,$',$0 /,$',$0
( (

linoleic acid #$%:' linoleic acid #$%:'Z Z


/,$' /,$'
( (

these acids are starting point for the synthesis of other fatty these acids are starting point for the synthesis of other fatty
acids by the human body: acids by the human body:

U U7linolenic acid 5.A, C:A 7linolenic acid 5.A, C:A

linoleic acid linoleic acid \ \7linolenic, arachidonic acid 7linolenic, arachidonic acid
9ipids 9ipids

Acylglycerols: Acylglycerols:

esters of glycerol with: esters of glycerol with:

one fatty acid monoacylglycerol #?AM( one fatty acid monoacylglycerol #?AM(

two fatty acids diacylglycerols #CAM( two fatty acids diacylglycerols #CAM(

three fatty acids triacylglycerols #TAM( three fatty acids triacylglycerols #TAM(

acylglycerols can be: acylglycerols can be:

amphipatic ?AM, CAM amphipatic ?AM, CAM

hydrophobic TAM hydrophobic TAM

triacylglycerols are classi)ed as: triacylglycerols are classi)ed as:

fats: fats:

solids or semisolids at room temperature solids or semisolids at room temperature

contain just saturated fatty acids or monounsaturated fatty acids contain just saturated fatty acids or monounsaturated fatty acids

oils: oils:

li+uids at room temperature li+uids at room temperature

contain polyunsaturated fatty acids contain polyunsaturated fatty acids


9ipids 9ipids

Acylglycerols: Acylglycerols:

TAM represent the bodyLs energy reservoir because: TAM represent the bodyLs energy reservoir because:

fatty acids are less o,idized than carbohydrates or proteins fatty acids are less o,idized than carbohydrates or proteins

TAM are hydrophobic and are stored in an anhydrous form TAM are hydrophobic and are stored in an anhydrous form

TAM are stored in specialized cells P TAM are stored in specialized cells P *%I6/48+, *%I6/48+, #adipose #adipose
tissue( tissue(

a sample of naturally occurring +*2 is a mixture of ?M K $M a sample of naturally occurring +*2 is a mixture of ?M K $M
chemical species that diNer according to their composition chemical species that diNer according to their composition
in fatty acids in fatty acids

?AM and CAM are intermediates in the catabolism and ?AM and CAM are intermediates in the catabolism and
biosynthesis of TAM biosynthesis of TAM
9ipids 9ipids

9ipids 9ipids

Mlycerophospholipids: Mlycerophospholipids:

major components of the cellular membranes major components of the cellular membranes

structural features: structural features:

contain glycerol as backbone contain glycerol as backbone

the hydro,yl groups from 9 the hydro,yl groups from 9


$ $
and 9 and 9
' '
are esteri)ed with fatty acids: are esteri)ed with fatty acids:

9 9
$ $
saturated fatty acids saturated fatty acids

9 9
' '
unsaturated fatty acids unsaturated fatty acids

the hydro,yl group from 9 the hydro,yl group from 9


2 2
is esteri)ed with phosphoric acid is esteri)ed with phosphoric acid

the phosphate group is involved in a second ester bond with the phosphate group is involved in a second ester bond with
a compound that contain a 7@: group: ethanolamine, a compound that contain a 7@: group: ethanolamine,
choline, serine, choline, serine, myo myo7inositol 7inositol

glycerophospholipids have: glycerophospholipids have:

a polar head a polar head

two hydrophobic tails two hydrophobic tails


9ipids 9ipids

9ipids 9ipids
polar head polar head
hydrophobic tails hydrophobic tails

Mlycerophospholipids: Mlycerophospholipids:

each type of glycerophospholipid is a mi,ture of compounds each type of glycerophospholipid is a mi,ture of compounds
that contain the same polar head and diferent fatty acyl that contain the same polar head and diferent fatty acyl
chains chains

glycerophospholipids are sensitive to diferent glycerophospholipids are sensitive to diferent


6)/6)/9I6*, 6)/6)/9I6*,: :

phospholipase A phospholipase A
' '
is present in the venom of bees and snakes is present in the venom of bees and snakes
9ipids 9ipids

Mlycerophospholipids a matter of stereochemistry: Mlycerophospholipids a matter of stereochemistry:

s s
9ipids 9ipids

<phingolipids: <phingolipids:

major components of the cellular membranes major components of the cellular membranes

derivatives of the amino alcohol derivatives of the amino alcohol 6)I-2/I-, 6)I-2/I-,: :

9 9
$% $%
unbranched carbon chain unbranched carbon chain

9 9
= =
has a has a trans trans 9P9 bond 9P9 bond

9 9
' '
amino group amino group

9 9
$ $
and 9 and 9
2 2
hydro,yl groups hydro,yl groups

9 9
' '
and 9 and 9
2 2
are asymmetric atoms are asymmetric atoms

the the - -7acyl fatty acid derivatives of sphigosine are called 7acyl fatty acid derivatives of sphigosine are called
4,'*1I%, 4,'*1I%,

clasiScation of shingolipids clasiScation of shingolipids: :

sphingomyelins sphingomyelins

cerebrosides cerebrosides

gangliosides gangliosides
9ipids 9ipids

<phingolipids: <phingolipids:

sphingomyelins: sphingomyelins:

the only class of sphingolipids that contains . the only class of sphingolipids that contains .

the 7@: from 9 the 7@: from 9


$ $
is bonded to: is bonded to:

phosphocholine phosphocholine

phosphoethanolamine phosphoethanolamine

major components of the myelin sheaths that insulate the major components of the myelin sheaths that insulate the
nerve )bers nerve )bers

cerebrosides: cerebrosides:

the 7@: from 9 the 7@: from 9


$ $
is bonded to a monosaccharide through a is bonded to a monosaccharide through a V V
glycosidic bond glycosidic bond

galactocerebrosides: galactocerebrosides:

have a single have a single V V7C7galactopyranosyl residue 7C7galactopyranosyl residue

glucocerebrosides: glucocerebrosides:

have a single have a single V V7C7glucopyranosyl residue 7C7glucopyranosyl residue


9ipids 9ipids

9ipids 9ipids
4ross section of myelinated
nerve fbers#

<phingolipids: <phingolipids:

gangliosides: gangliosides:

contains comple, chains of oligosaccharides contains comple, chains of oligosaccharides

the only class of sphingolipids that contain one or more the only class of sphingolipids that contain one or more
residues of sialic acid residues of sialic acid

particular system of nomenclature: particular system of nomenclature:

M M
?$ ?$
? indicates the presence of only one sialic acid residue ? indicates the presence of only one sialic acid residue

M M
C$ C$
C indicates the presence of two sialic acid residues C indicates the presence of two sialic acid residues

all shingolipids have amphipatic molecules all shingolipids have amphipatic molecules
9ipids 9ipids

9ipids 9ipids

<teroidsI<terols: <teroidsI<terols:

compounds found mostly in eukaryotic cells compounds found mostly in eukaryotic cells

derivatives of derivatives of >"?-4849/6,-+*-/6,')8%'/6),-*-+)',-, >"?-4849/6,-+*-/6,')8%'/6),-*-+)',-,

cholesterol: cholesterol:

component of animal plasma membranes component of animal plasma membranes

it is the precursor of all steroid hormones: it is the precursor of all steroid hormones:

glucocorticoids glucocorticoids cortisol cortisol

mineralocorticoids mineralocorticoids aldosterone aldosterone

sex hormones sex hormones androgens #testosterone( and estrogens # androgens #testosterone( and estrogens #V V7estradiol( 7estradiol(

the only way to catabolize cholesterol is to convert it to bile acids the only way to catabolize cholesterol is to convert it to bile acids
#animal cells are not able to open the =7rings structure( #animal cells are not able to open the =7rings structure(
9ipids 9ipids

9ipids 9ipids

5icosanoids: 5icosanoids:

collective term used to describe a large group of compounds collective term used to describe a large group of compounds
with '& carbon atoms #greek: with '& carbon atoms #greek: eikosi eikosi, twenty( , twenty(

general features: general features:

contain o,ygen atoms contain o,ygen atoms

are biologically active at very low concentrations are biologically active at very low concentrations

act as local mediators: act as local mediators:

paracrine mediators paracrine mediators

autocrine mediators autocrine mediators

they are not stored inside cells but rather are synthesized when they are not stored inside cells but rather are synthesized when
needed needed

in>uence a variety of physiological processes: in>uence a variety of physiological processes:

in>ammation in>ammation

blood pressure and blood clotting blood pressure and blood clotting

fever fever

pain pain

labor induction labor induction


9ipids 9ipids

5icosanoids: 5icosanoids:

clasiScation: clasiScation:

classic eicosanoids: classic eicosanoids:

prostaglandins #.M( prostaglandins #.M(

.rostacyclins .rostacyclins #.MH( #.MH(

thrombo,anes #T,( thrombo,anes #T,(

leukotrienes #-T( leukotrienes #-T(

non7classic eicosanoids: non7classic eicosanoids:

resolvins resolvins

hepo,ilins hepo,ilins

isofurans isofurans

isoprostanes isoprostanes
9ipids 9ipids

5icosanoids: 5icosanoids:

precursors of eicosanoids are the following fatty acids: precursors of eicosanoids are the following fatty acids:

dihomo- dihomo-O O-linolenic acid -linolenic acid: :

contains 2 9P9 double bonds contains 2 9P9 double bonds

precursor of X precursor of Xseries-> series->* prostaglandins #contain $ 9P9 double bond( * prostaglandins #contain $ 9P9 double bond(

arachidonic acid arachidonic acid: :

contains = 9P9 double bonds contains = 9P9 double bonds

precursor of X precursor of Xseries-? series-?* prostaglandins #contain ' 9P9 double bonds( * prostaglandins #contain ' 9P9 double bonds(

eicosapentaenoic acid eicosapentaenoic acid: :

cotains 0 9P9 double bonds cotains 0 9P9 double bonds

precursor of X precursor of Xseries-$ series-$* prostaglandins #contain 2 9P9 double bonds( * prostaglandins #contain 2 9P9 double bonds(

in humans the most prevalent eicosanoid precursor is in humans the most prevalent eicosanoid precursor is
arachidonic acid arachidonic acid
9ipids 9ipids

5icosanoids: 5icosanoids:

nomenclature of prostaglandins: nomenclature of prostaglandins:

two7letter abbreviation #.M( two7letter abbreviation #.M(

letter indicating the ring type #A H( letter indicating the ring type #A H(

subscript indicating the number of 9P9 bonds subscript indicating the number of 9P9 bonds

U UI IV V indicating the con)guration of two 7@: groups in certain .Ms indicating the con)guration of two 7@: groups in certain .Ms

<une Bergstr <une Bergstr"m, "m, Bengt Hngemar <amuelsson, ;ohn Bobert Bengt Hngemar <amuelsson, ;ohn Bobert
Gane #8obel .rize in ?edicine and .hysiology $/%'( Gane #8obel .rize in ?edicine and .hysiology $/%'(
9ipids 9ipids

5icosanoids: 5icosanoids:

biosynthesis re+uires two diferent enzymes: biosynthesis re+uires two diferent enzymes:

cyclooxygenase cyclooxygenase (4/&) (4/&): :

involved in the synthesis of involved in the synthesis of .Ms, T,s, .MHs( .Ms, T,s, .MHs(

it involves a transient carbon radical it involves a transient carbon radical

it has two enzymatic activities: it has two enzymatic activities:

cycloo,ygenase cycloo,ygenase

hydropero,idase hydropero,idase

inhibited by aspirin inhibited by aspirin

lipoxygenase lipoxygenase: :

involved in the synthesis of leukotrienes involved in the synthesis of leukotrienes

it is not inhibited by aspirin it is not inhibited by aspirin


9ipids 9ipids

9ipids 9ipids

5icosanoids 5icosanoids some practical aspects some practical aspects: :

how does aspirin relieve pain and reduce in>ammationQ how does aspirin relieve pain and reduce in>ammationQ

aspirin #acetylsalicylic acid( blocks 9@F activity aspirin #acetylsalicylic acid( blocks 9@F activity

the acetyl group is transfered from aspirin to the 7@: group of the acetyl group is transfered from aspirin to the 7@: group of
a serine residue of the enzyme # a serine residue of the enzyme #irreversibile covalent irreversibile covalent
modifcation modifcation( (

as a result the synthesis of proin>ammatory .Ms is inhibited as a result the synthesis of proin>ammatory .Ms is inhibited

from a chemical point of view P from a chemical point of view P transesterifcation reaction transesterifcation reaction
9ipids 9ipids

5icosanoids some practical aspects: 5icosanoids some practical aspects:

CH8@.B@<T@85: CH8@.B@<T@85:

generic name of .M5 generic name of .M5


' '

induces smooth muscle rela,ation induces smooth muscle rela,ation

it is used to induce labor and abortion it is used to induce labor and abortion

?H<@.B@<T@-: ?H<@.B@<T@-:

it is a synthetic analogue of .M5 it is a synthetic analogue of .M5


$ $

it is sold as a mi,ture of stereoisomers it is sold as a mi,ture of stereoisomers

it is used to prevent gastric ulcers #blocks the :9l secretion it is used to prevent gastric ulcers #blocks the :9l secretion
into stomac by specialized cells( into stomac by specialized cells(
9ipids 9ipids

Biological membranes: Biological membranes:

amphipatic molecules can form: amphipatic molecules can form:

monolayers monolayers: :

polar groups are oriented toward the water polar groups are oriented toward the water

hydrocarbon tails e,tend into the air hydrocarbon tails e,tend into the air

micelles micelles: :

hydrocarbon tails associates towards the center of the structure hydrocarbon tails associates towards the center of the structure

polar groups are oriented toward the e,terior #water( polar groups are oriented toward the e,terior #water(

are formed at a speci)c concentration # are formed at a speci)c concentration #414 414, , c critical ritical m micelle icelle
c concentration( oncentration(

only compounds with one hydrophobic tail form micelles # only compounds with one hydrophobic tail form micelles #fatty acids salts fatty acids salts( (

bilayers bilayers: :

are made by compounds that contain two hydrophobic tails are made by compounds that contain two hydrophobic tails
# #glycerophospholipids glycerophospholipids, , sphingolipids sphingolipids( (

contain two monolayers: contain two monolayers:

the hydrocarbon tails point toward the interior of the bilayer the hydrocarbon tails point toward the interior of the bilayer

the polar groups are in contact with water environment the polar groups are in contact with water environment
9ipids 9ipids

9ipids 9ipids

Biological membranes Biological membranes the >uid mosaic model the >uid mosaic model: :

proposed by <E;onathan <inger and Marth -E 8icolson #$/3'( proposed by <E;onathan <inger and Marth -E 8icolson #$/3'(

describes the arrangement of lipids and proteins into a describes the arrangement of lipids and proteins into a
membrane membrane

a membrane is a dynamic structure in which both lipids and a membrane is a dynamic structure in which both lipids and
proteins can do some movements proteins can do some movements: :

movements of lipids: movements of lipids:

lateral difusion a rapid process lateral difusion a rapid process

transverse difusion a slow process transverse difusion a slow process


#!:RQ]( #!:RQ](

movements of proteins: movements of proteins:

lateral difusion lateral difusion


9ipids 9ipids

9ipids 9ipids

Biological membranes the >uid mosaic model: Biological membranes the >uid mosaic model:

the >uidity of a lipid bilayer depends on several factors: the >uidity of a lipid bilayer depends on several factors:

lipid composition lipid composition: :

saturated fatty acids great tendency to aggregate # saturated fatty acids great tendency to aggregate #Puidity decreases Puidity decreases( (

unsaturated fatty acids disrupt the regulated packing # unsaturated fatty acids disrupt the regulated packing #Puidity increases Puidity increases( (

cholesterol interferes with the motion of fatty acid tails # cholesterol interferes with the motion of fatty acid tails #Puidity Puidity
decreases decreases( (

structure of the hydrophobic tails structure of the hydrophobic tails: :

saturated versus unsaturated fatty acids saturated versus unsaturated fatty acids

short versus long fatty acids short versus long fatty acids

temperature temperature: :

there is a there is a transition phase temperature transition phase temperature

below transition phase temperature the lipid bilayer becomes a gel7like below transition phase temperature the lipid bilayer becomes a gel7like
solid solid

above transition phase temperature the lipid bilayer becomes more >uid above transition phase temperature the lipid bilayer becomes more >uid

there is a variation of the bilayerLs thickness during the transition phase there is a variation of the bilayerLs thickness during the transition phase
9ipids 9ipids

Biological membranes the >uid mosaic model: Biological membranes the >uid mosaic model:

in vivo in vivo, the lipid composition of the membrane bilayer , the lipid composition of the membrane bilayer
addapts in order to keep the membranesL >uidity: addapts in order to keep the membranesL >uidity:

bacteria grown at low temperatures increase the proportion of bacteria grown at low temperatures increase the proportion of
unsaturated fatty acids in their membrane lipids unsaturated fatty acids in their membrane lipids

gold)sh in low temperature waters increase the proportion of gold)sh in low temperature waters increase the proportion of
unsaturated fatty acids in their membrane lipids unsaturated fatty acids in their membrane lipids

polar bears have a higher proportion of unsaturated fatty acids polar bears have a higher proportion of unsaturated fatty acids
in their membrane lipids in their membrane lipids

these adaptations enable the membranes to keep their these adaptations enable the membranes to keep their
Puidity and the biological functions Puidity and the biological functions
9ipids 9ipids

Biological membranes the proteins: Biological membranes the proteins:

there are three types of membrane proteins: there are three types of membrane proteins:

integral membrane proteins: integral membrane proteins:

contain a hydrophobic region embedded in the lipid bilayer contain a hydrophobic region embedded in the lipid bilayer

the membrane7spanning segment contains the membrane7spanning segment contains U U heli, or a heli, or a V V7barrel 7barrel
segments segments

peripheral membrane proteins: peripheral membrane proteins:

located either on the outer or the inner face of a membrane located either on the outer or the inner face of a membrane

associated with membraneLs lipids and proteins through ionic associated with membraneLs lipids and proteins through ionic
interactions and hydrogen bonds interactions and hydrogen bonds

lipid anchored membrane proteins: lipid anchored membrane proteins:

fatty acid anchor fatty acid anchor myristicIpalmitic acid bound covalently through an myristicIpalmitic acid bound covalently through an
esterIamide bond to an amino acid residue of the protein esterIamide bond to an amino acid residue of the protein

prenyl anchor prenyl anchor isoprenoid chain bound covalently through the sulfur isoprenoid chain bound covalently through the sulfur
atom of a cysteine residue of the protein atom of a cysteine residue of the protein

26I anchor 26I anchor the protein is linked through a the protein is linked through a
glycosylphosphatidylinositol molecule #the most fre+uent in glycosylphosphatidylinositol molecule #the most fre+uent in
eukaryotic cells( eukaryotic cells(
9ipids 9ipids

9ipids 9ipids
fatty acid anchor fatty acid anchor
prenyl anchor prenyl anchor
26I anchor 26I anchor

8ucleotides: 8ucleotides:

major biomolecules major biomolecules: :

components of the nucleic acids: components of the nucleic acids:

C8A #deo,yribonucleic acid( encodes the hereditary information C8A #deo,yribonucleic acid( encodes the hereditary information

B8A #ribonucleic acid( B8A #ribonucleic acid(

components of diferent coenzymes: components of diferent coenzymes:

8AC 8AC
4 4
I8AC:, 8AC. I8AC:, 8AC.
4 4
I8AC.: I8AC.:

ACIAC: ACIAC:
' '
, ?8I?8: , ?8I?8:
' '

coenzyme A coenzyme A

phosphorylating agents: AT. phosphorylating agents: AT.

nucleotides contain three components: nucleotides contain three components:

a nitrogenous compound BA<5 a nitrogenous compound BA<5

a )ve7carbon sugar a )ve7carbon sugar

one or more #2( phosphate groups one or more #2( phosphate groups
-ucleotides and nucleic acids -ucleotides and nucleic acids

8itrogenous compounds the bases: 8itrogenous compounds the bases:

structural features of the bases: structural features of the bases:

heterocyclic molecules heterocyclic molecules

planar molecules planar molecules

aromatic compounds aromatic compounds derivatives of derivatives of: :

purine purine

pyrimidine pyrimidine

classi)cation of bases: classi)cation of bases:

purines: purines:

adenine #67aminopurine( adenine #67aminopurine(

guanine #'7amino767o,opurine( guanine #'7amino767o,opurine(

pyrimidines: pyrimidines:

uracil #',=7dio,opyrimidine( uracil #',=7dio,opyrimidine(

thymine #',=7dio,o707methylpyrimidine( thymine #',=7dio,o707methylpyrimidine(

cytosine #'7o,o7=7aminopyrimidine( cytosine #'7o,o7=7aminopyrimidine(


-ucleotides and nucleic acids -ucleotides and nucleic acids

8itrogenous compounds the tautomerism: 8itrogenous compounds the tautomerism:

tautomers K isomers that diNer in the location of a double tautomers K isomers that diNer in the location of a double
bond and a hydrogen atom bond and a hydrogen atom

purines tautomers: purines tautomers:

amino imino tautomers which are in e+uilibria amino imino tautomers which are in e+uilibria

at physiological p: the e+uilibria lies in the direction of the at physiological p: the e+uilibria lies in the direction of the
amino form amino form

pyrimidines tautomers: pyrimidines tautomers:

lactam lactim tautomers which are in e+uilibria lactam lactim tautomers which are in e+uilibria

this is a form of keto7enol tautomerism this is a form of keto7enol tautomerism

at physiological p: the e+uilibria lies in the direction of the at physiological p: the e+uilibria lies in the direction of the
lactam form lactam form

the tautomers enables the base pairing in nucleic acids the tautomers enables the base pairing in nucleic acids
-ucleotides and nucleic acids -ucleotides and nucleic acids

-ucleotides and nucleic acids -ucleotides and nucleic acids

8ucleosides: 8ucleosides:

compounds containing: compounds containing:

a base a base

an aldopentose: an aldopentose:

C7ribose # C7ribose #V V7C7ribofuranose( B8A 7C7ribofuranose( B8A

'7deo,y7C7ribose #'7deo,y7 '7deo,y7C7ribose #'7deo,y7V V7C7ribofuranose( C8A 7C7ribofuranose( C8A

the the V V7 7- -7glycosidic bond connects: 7glycosidic bond connects:

the anomeric carbon atom of the pentose the anomeric carbon atom of the pentose

the 87$ of the pyrimidines the 87$ of the pyrimidines

the 87/ of the purines the 87/ of the purines

the designation of atoms in nucleosides: the designation of atoms in nucleosides:

the atoms of the bases are numbered $, ', 2 etc the atoms of the bases are numbered $, ', 2 etc

the atoms of the pentose are numbered $L, 'L, 2L etc the atoms of the pentose are numbered $L, 'L, 2L etc
-ucleotides and nucleic acids -ucleotides and nucleic acids

-ucleotides and nucleic acids -ucleotides and nucleic acids

8ucleosides: 8ucleosides:

naming the nucleosides: naming the nucleosides:

the name of a nucleoside derives from the corresponding base the name of a nucleoside derives from the corresponding base

systematic name: systematic name:

diScult to use: adenosine #/7 diScult to use: adenosine #/7V V7C7ribofuranosyladenine( 7C7ribofuranosyladenine(

working names working names: :

are use in biochemical routine: adenosine #B8A(Ideo,yadenosine are use in biochemical routine: adenosine #B8A(Ideo,yadenosine
#C8A(, cytidine #B8A(Ideo,ycytidine #C8A( #C8A(, cytidine #B8A(Ideo,ycytidine #C8A(

rotation around the rotation around the - -7glycosidic bond give rises to: 7glycosidic bond give rises to:

syn syn conformation conformation: :

the base lies directly above the sugar the base lies directly above the sugar

anti anti conformation conformation: :

the base lies away from the sugar the base lies away from the sugar

the predominant conformation the predominant conformation in vivo in vivo


-ucleotides and nucleic acids -ucleotides and nucleic acids

-ucleotides and nucleic acids -ucleotides and nucleic acids

8ucleotides: 8ucleotides:

phosphorylated derivatives of nucleosides phosphorylated derivatives of nucleosides

characteristics of nucleotides: characteristics of nucleotides:

have $, ' or 2 phosphate groups attached usually to the 0L have $, ' or 2 phosphate groups attached usually to the 0L
position: position:

8?. nucleoside monophosphate 8?. nucleoside monophosphate

8C. nucleoside diphosphate 8C. nucleoside diphosphate

8T. nucleoside triphosphate 8T. nucleoside triphosphate

are anions at physiological p: are anions at physiological p:

8C. and 8T. contain one and two phosphoanhydride bonds 8C. and 8T. contain one and two phosphoanhydride bonds
-ucleotides and nucleic acids -ucleotides and nucleic acids

8ucleic acids: 8ucleic acids:

classi)cation of nucleic acids: classi)cation of nucleic acids:

deo,yribonucleic acid #C8A( encodes the hereditary information deo,yribonucleic acid #C8A( encodes the hereditary information

ribonucleic acid #B8A( produced through the transcription of C8A ribonucleic acid #B8A( produced through the transcription of C8A

C8A was isolated in $%6/ from the nuclei of white blood cells: C8A was isolated in $%6/ from the nuclei of white blood cells:

nucleus nucleus nucleic nucleic

acidic compound acidic compound acid acid

general characteristics: general characteristics:

polynucleotides the succesive nucleosides are linked through polynucleotides the succesive nucleosides are linked through
phosphodiester bonds phosphodiester bonds between: between:

0L hydro,yl group of one nucleoside 0L hydro,yl group of one nucleoside

2L hydro,yl group of the ne,t nucleoside 2L hydro,yl group of the ne,t nucleoside

macromolecules with directionality: macromolecules with directionality:

0L7end usually has a phosphate group attached to the 0L of the 0L7end usually has a phosphate group attached to the 0L of the
pentose pentose

2L7end has a free hydro,yl group at 2L 2L7end has a free hydro,yl group at 2L
-ucleotides and nucleic acids -ucleotides and nucleic acids

-ucleotides and nucleic acids -ucleotides and nucleic acids

Ceo,yribonucleic acid #C8A(: Ceo,yribonucleic acid #C8A(:

large molecules: large molecules:

up to '=0 million nucleotides up to '=0 million nucleotides

molecular weights up to 30 bilion Ca #Caltons( molecular weights up to 30 bilion Ca #Caltons(

represents the represents the 2,-/1, 2,-/1, of a cell of a cell

contains: contains:

'7deo,y7C7ribose '7deo,y7C7ribose

bases: A, 9, M and T bases: A, 9, M and T

primary structure primary structure: :

indicates the se+uence of bases in a strand indicates the se+uence of bases in a strand

writing convention writing convention: : the se+uence is written from left to right the se+uence is written from left to right
#from 0L to 2L end( #from 0L to 2L end(

secondary structure secondary structure: :

indicates the association of two strands forming a indicates the association of two strands forming a double-helix double-helix
-ucleotides and nucleic acids -ucleotides and nucleic acids

Ceo,yribonucleic acid the 9hargafLs rules: Ceo,yribonucleic acid the 9hargafLs rules:

the 9hargaf the 9hargafLs Ls rules rules: :

proposed by 5rwin 9hargaf in late $/=&s proposed by 5rwin 9hargaf in late $/=&s

the )rst +uantitative relationships between the bases in C8A: the )rst +uantitative relationships between the bases in C8A:

^A_ P ^T_ ^A_ P ^T_

^M_ P ^9_ ^M_ P ^9_

^purines_I^pyrimidines_ P $ ^purines_I^pyrimidines_ P $

these quantitative relations" the known structures of these quantitative relations" the known structures of
nucleotides and the &-ray diNraction patterns ('osalind nucleotides and the &-ray diNraction patterns ('osalind
0ranklin" 1aurice (ilkins) enables (atson and 4rick to propose 0ranklin" 1aurice (ilkins) enables (atson and 4rick to propose
in >LA$ the %/.D9,-),9I& +'.4+.', /0 %-* in >LA$ the %/.D9,-),9I& +'.4+.', /0 %-*

the 4hargaN!s rules are explained by the base-pairing the 4hargaN!s rules are explained by the base-pairing
through hydrogen bonds through hydrogen bonds
-ucleotides and nucleic acids -ucleotides and nucleic acids

-ucleotides and nucleic acids -ucleotides and nucleic acids

Ceo,yribonucleic acid the double7heli, model: Ceo,yribonucleic acid the double7heli, model:

the major features of the !atson79rick model of C8A: the major features of the !atson79rick model of C8A:

two polynucleotide chains wind around a common a,is #double two polynucleotide chains wind around a common a,is #double
heli,( heli,(

the two chains are antiparallel: the two chains are antiparallel:

run in opposite directions #0L 2LI2L 0L( run in opposite directions #0L 2LI2L 0L(

each chain forms a left7handed heli, each chain forms a left7handed heli,

the bases occupy the core of the heli, the bases occupy the core of the heli,

the sugars7phosphate chains run along the periphery, the sugars7phosphate chains run along the periphery,
minimizing the repulsions between the charged phosphate minimizing the repulsions between the charged phosphate
groups groups

each base is hydrogen bonded to a base in the opposite strand each base is hydrogen bonded to a base in the opposite strand
# #the two chains are complementary the two chains are complementary( (
-ucleotides and nucleic acids -ucleotides and nucleic acids

Ceo,yribonucleic acid the double heli, model: Ceo,yribonucleic acid the double heli, model:

the structural features of the !atson79rick model of C8A: the structural features of the !atson79rick model of C8A:

the bases are planar and parallel the bases are planar and parallel

the bases are almost perpendicular on the sugar7phosphate the bases are almost perpendicular on the sugar7phosphate
backbone backbone

the heli, is '& the heli, is '& N wide N wide

there are $& basesIturn there are $& basesIturn

one turn is 2= N in length one turn is 2= N in length

the double7heli, has: the double7heli, has:

a major groove $' a major groove $' N wide N wide

a minor groove 6 N wide a minor groove 6 N wide

these grooves enable the interaction of the C8A with: these grooves enable the interaction of the C8A with:

diferent proteins involved in replication, transcription and reparation diferent proteins involved in replication, transcription and reparation

diferent drugs with antibacterial and anticancer activity diferent drugs with antibacterial and anticancer activity
-ucleotides and nucleic acids -ucleotides and nucleic acids

-ucleotides and nucleic acids -ucleotides and nucleic acids

Ceo,yribonucleic acid the forces that stabilize the double7heli,: Ceo,yribonucleic acid the forces that stabilize the double7heli,:

weak interactions weak interactions: :

stacking interactions stacking interactions: :

purines and pyrimidines tend to form e,tended stacks of planar parallel purines and pyrimidines tend to form e,tended stacks of planar parallel
molecules molecules

probably there are van der !aals interactions probably there are van der !aals interactions

hydrogen bonds hydrogen bonds: :

between bases from the two strands #AIT, MI9( between bases from the two strands #AIT, MI9(

hydrophobic eNect hydrophobic eNect: :

the hydrophobic bases are buried in the interior of the double7heli, the hydrophobic bases are buried in the interior of the double7heli,

the surface area of the non7polar residues e,posed to water decreases the surface area of the non7polar residues e,posed to water decreases
increases the entropy of the surrounding water mollecules increases the entropy of the surrounding water mollecules

ionic interactions ionic interactions: :

the negative charges of the phosphate groups belonging to the sugar7 the negative charges of the phosphate groups belonging to the sugar7
phosphate backbone are opposed by cations #?g phosphate backbone are opposed by cations #?g
'4 '4
( or positive charged ( or positive charged
proteins proteins
-ucleotides and nucleic acids -ucleotides and nucleic acids

Ceo,yribonucleic acid the forces that stabilize the double7heli,: Ceo,yribonucleic acid the forces that stabilize the double7heli,:

t the he interactions that stabilize the interactions that stabilize the double7heli, can be broken: double7heli, can be broken:

in vivo in vivo enzymes #helicases( enzymes #helicases(

in vitro in vitro temperature temperature

the disruption of these forces is needed the disruption of these forces is needed in vivo in vivo during: during:

C8A replication C8A replication

C8A repair C8A repair

B8A synthesis #transcription( B8A synthesis #transcription(

melting temperature # melting temperature #+ +


m m
(: (:

the temperature at which half the C8A has become single the temperature at which half the C8A has become single
stranded stranded

absorption at '6& nm increases during the e,periment # absorption at '6& nm increases during the e,periment #melting melting
curve curve( (

the value depends on basesL composition #:@!Q( the value depends on basesL composition #:@!Q(
-ucleotides and nucleic acids -ucleotides and nucleic acids

-ucleotides and nucleic acids -ucleotides and nucleic acids
hyperchromic efect hyperchromic efect

Bibonucleic acid #B8A(: Bibonucleic acid #B8A(:

smaller molecules: smaller molecules:

as few as '$ nucleotides as few as '$ nucleotides

molecular weights up to 3&&& Ca molecular weights up to 3&&& Ca

contain: contain:

C7ribose C7ribose

bases: A, M, 9, and W bases: A, M, 9, and W

primary structure primary structure: :

indicates the se+uence of bases in a strand #same convention indicates the se+uence of bases in a strand #same convention
as for C8A( as for C8A(

secondary structure secondary structure: :

indicates the regions which associate to form intramolecular indicates the regions which associate to form intramolecular
double7heli,es double7heli,es

tertiary structure tertiary structure: :

indicates the 2C structure of the molecule indicates the 2C structure of the molecule
-ucleotides and nucleic acids -ucleotides and nucleic acids

-ucleotides and nucleic acids -ucleotides and nucleic acids
Secondary and tertiary structures of tRNA molecule. Secondary and tertiary structures of tRNA molecule.

Bibonucleic acid classi)cation: Bibonucleic acid classi)cation:

ribosomal '-* (r'-*) ribosomal '-* (r'-*): :

small B8A molecules small B8A molecules

components of the ribosomes components of the ribosomes

involved in translation #protein synthesis( involved in translation #protein synthesis(

transfer '-* (t'-*) transfer '-* (t'-*): :

activates amino acids for protein synthesis #translation( activates amino acids for protein synthesis #translation(

contains some unusual nucleosides #ribothymidine, contains some unusual nucleosides #ribothymidine,
pseudouridine, dihydrouridine( pseudouridine, dihydrouridine(

messenger '-* (m'-*) messenger '-* (m'-*): :

encodes the se+uence of amino acids in proteins encodes the se+uence of amino acids in proteins

X Xcarry* the genetic information from C8A to ribosomes for carry* the genetic information from C8A to ribosomes for
protein synthesis protein synthesis
-ucleotides and nucleic acids -ucleotides and nucleic acids

8ucleic acids the >ow of genetic information: 8ucleic acids the >ow of genetic information:

the >ow of genetic information in a cell: the >ow of genetic information in a cell:

was described by rancis 9rick as X was described by rancis 9rick as X4,-+'*9 %/21* /0 4,-+'*9 %/21* /0
1/9,4.9*' 2,-,+I4 1/9,4.9*' 2,-,+I4* *

C8A stores the genetic information C8A stores the genetic information

B8A decodes the information from C8A and enables the B8A decodes the information from C8A and enables the
synthesis of proteins synthesis of proteins

the >ow of genetic information in a cell makes reference to the >ow of genetic information in a cell makes reference to
three biochemical processes: three biochemical processes:

replication synthesis of C8A replication synthesis of C8A

transcription synthesis of B8A transcription synthesis of B8A

translation synthesis of proteins translation synthesis of proteins


-ucleotides and nucleic acids -ucleotides and nucleic acids

-ucleotides and nucleic acids -ucleotides and nucleic acids

Beplication: Beplication:

s s
-ucleotides and nucleic acids -ucleotides and nucleic acids