Chemistry of Carbohydrates

By:- Behailu Tsegaye

 Topic to be covered under this chapter

Carbohydrate: Structure, properties, functions and

reactivity

 Classification of Carbohydrates

Monosaccharides
Oligosaccharides
Polysaccharides 2
By the end of this lecture you are able to
• Mention Structure, properties, functions and reactivity
of Carbohydrate

• Classifies Carbohydrates

• list some Qualitative and quantitative test for

carbohydrates

• Distinguish chiral from achiral molecules

• Identify stereo-chemistry in carbohydrates

• Create simple Fisher Projections, identify Haworth

projections
• Name and identify all members of the3
aldose and ketose
carbohydrate families
 Introduction
Definition

Carbohydrates (sugars) are organic compounds

containing carbon, hydrogen and oxygen with the
general formula CnH2nOn, where, hydrogen and
oxygen are present in 1:2 ratio like that in water.

They may be regarded as hydrates of carbons with

one molecule of water for each carbon atom, i.e.,
Cn(H2O)n.
4
 Introduction Cont.…….
 Some of the substances classified as carbohydrates may
not fullfill the above formula with ratio of carbon, oxygen
and hydrogen, e.g., Rhamnose (C6H12O5), amino sugars
(Glucosamine, C6H13O5N) and deoxy sugars like
deoxyribose (C5H10O4).

 In
addition, certain other carbohydrates are now known to
possess nitrogen (e.g., glucosamine, C6H13O5N),
phosphorus or sulfur also and obviously do not coincide
5

with the above general formula.

 Introduction Cont.….
whereas there are some non-carbohydrate compounds which
have the same formula as defined for carbohydrates, i.e.
CnH2nOn.

Examples :- acetic acid (CH3COOH, C2H4O2) and lactic

acid (C3 H6 O3) formaldehyde (CH2O), that are not
carbohydrates.

Carbohydrates are also known as “saccharides”

(sakcharon in Greek means = sugar or sweetness) since
many of those of relatively small molecular weight have a
6
sweet taste, although this is not true of those with large
molecules.
 Introduction Cont.…
 Generally Carbohydrate defined as
It is Polyhydroxy aldehydes or ketones or compounds
that yield these derivatives on hydrolysis.

7
 Property of carbohydrate
Existence of at least one & often two or more asymmetric
centers (chiral) carbon (a carbon atom attached to four
chemically different groups) and are, therefore, optically
active.

Ability to exist either in linear or ring structures.

Capacity to form polymeric structures via glycosidic bonds.

Potential to form multiple hydrogen bonds with water or
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other molecules in their environment.
 Functions of carbohydrates
 Carbohydrate oxidation provides energy, 4.2kcal/gm). Brain
cells and RBCs are almost wholly dependent on
carbohydrates as the energy source.

 Carbohydrate stored in the form of glycogen, provides a

short-term energy reserve. Relatively ease to be stored, when
in excess, and mobilized, when needed, makes them
excellent energy storage molecules.

 Serve as structural component of some cells and tissues

 Uses as Dietary fibers
 Carbohydrates
form part of the structural framework of DNA
and RNA molecules & metabolic precursors of 9 all
other biomolecules
 Function of Carbohydrate Cont.…

 Participate in the structure of cell membrane & cellular functions

(cell growth, adhesion and fertilization).
 Carbohydrates are precursors for many organic compounds by
supplying carbon atoms for the synthesis of other biochemical
substances (proteins, lipids, and nucleic acids)
 Lubricate skeletal joints and participate in recognition and
adhesion between cells

 Carbohydrates linked to lipids are structural components of cell

membranes.

 Carbohydrates linked to proteins function in a variety of cell–cell

and cell–molecule recognition processes etc.….. 10
 Carbohydrates
FUNCTION Biological roles Cont.
CONT…..

Carbohydrates
. produced in plants,
 such as glucose are
synthesized from
CO2, H2O, and energy
from the sun.
 .are oxidized in living
cells to produce CO2,
H2O, and energy.
11
 Occurrence of carbohydrates
 Carbohydrates are the most abundant class of bioorganic
molecules on planet Earth
 In the human body about 2% of Carbohydrates present
 Carbohydrates constitute about 75% by mass of dry plant
materials
 Green plants produce carbohydrates via photosynthesis

 Plants have two main uses for the carbohydrates they

produce.
 In the form of cellulose, serve as structural elements
 In the form of starch, they provide energy reserves for 12

them selves
 Sources
 In plants
 glucose is synthesized from CO2 and H2O and
stored as starch or converted to cellulose of
plant frame work.

Photosynthesis
6CO2 + 6H2O + Energy C6H12O6 + 6O2
Respiration

 Animals Can synthesize carbohydrate

 from protein and indirectly from fats

 but the primary sources are plants(dietary
staple)
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14
CLASSIFICAIONT OF CARBOHYDRATES

Monosaccharides

Oligosaccharides

Polysaccharides

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 CLASSIFICAIONT OF CARBOHYDRATES

According to the number of sugar units and the size of the molecule, they
could be grouped into three types:

 Monosaccharides: (simple sugars): They are simplest form of sugars,

which cannot be further hydrolyzed. They represent the building units and
hydrolytic end products of the more complex carbohydrates.
 It crystalline, water soluble substances
 Oligosaccharides: These are the conjugates of carbohydrates where 2-10
monosaccharide units are linked to each other.
 A disaccharide: are the most common type of oligosaccharide that
contains two monosaccharide units covalently bonded to each other.
Like monosaccharides, disaccharides are crystalline, water soluble
substances
 Polysaccharides: These are higher polymers of carbohydrates and contain
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more than 10 monosaccharide units per molecule.
Monosaccharides
Single polyhydroxy aldehyde or ketone
unit

Pure monosaccharides are water-

soluble, white and crystalline solids

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 Monosaccharaides
 Represent the building units and hydrolytic end products of the
more complex carbohydrates.
 All except dihydroxyacetone contain at least one asymmetrical
(chiral) carbon and it is optically active.

 They exist in either of the two conformations, D or L, based on the

position of the OH group asymmetric carbon furthest from the
carbonyl carbohydrate

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 Classification of monosaccharides

Monosaccharides with three to seven carbon atoms are

commonly found in nature.
 Classified by their number of carbon atoms

Name Formula
trios e C3 H6 O 3
tetrose C4 H8 O 4
pentose C 5 H 1 0 O5
hexose C 6 H 1 2 O6
heptose C 7 H 1 4 O7
octose C 8 H 1 6 O8
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 Classification Cont…
Classified on the basis of type of O
carbonyl group as aldoses or ║
ketoses C─H aldose
Aldoses are │
monosaccharides H─ C─OH
• with an aldehyde group │
H─ C─OH
• with many hydroxyl (-OH)
│
groups. CH2OH
triose (3C atoms)
tetrose (4C atoms) Erythose, an
aldotetrose
pentose (5 C atoms)
hexose (6 C atoms) 20
 D-Aldoses
(pentose)
(triose) (tetrose)

( stereoisomers of the hexoses)

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 Ketoses
Ketoses are
monosaccharides CH2OH
• with a ketone group │
C=O ketose
• with many hydroxyl (- │
OH) groups. H─ C─OH
│
H─ C─OH
│
H─C─OH
│
CH2OH
Fructose, a ketohexose
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 D-ketoses

Note:
Ketoses have one
fewer asymmetric
center than do
aldoses with the
same number of
carbons

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 Classification Cont…

Classified by both their number of carbon atoms and their

functional group
 A six-carbon monosaccharide with an aldehyde
functional group is an aldohexose; a five-carbon
monosaccharide with a ketone functional group is a
ketopentose.

Monosaccharides are also often called sugars.

 Hexoses are six-carbon sugars, pentoses five-carbon

sugars, and so on.
25
 NAMING OF MONOSACCHARIDES

Based on the number Based on the

of carbon atom functional group

Note: the suffix – ulose is for ketone group, rose for aldehyde group
26
 Naming of monosaccharides
1. According to the presence of aldehyde or ketone group:
Aldose Vs ketose
2. According to the presence number of carbon atoms:
Trioses, tetroses, pentoses, Hexoses, heptoses
3. According to both the presence of aldehyde or ketone groups and
number of carbon atoms:
Aldotrioses Vs ketotrioses, aldohexoses Vs ketohexoses etc.

4. According to positions of hydroxyl groups on asymmetrical carbon

atoms (stereoisomers like D or L configuration, epimers,
anomers..)

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28
 IMPORTANCE OF MONOSACCHARIDES
 GLUCOSE
Energy source for cells in the body
Brain cells, RBCs cells that have not Mitochondria and
the growing embryo only utilize glucose as a source of
energy
Cells such as eyeballs have limited oxygen supply and
use large amount of glucose to generate energy
The storage energy in humans in the form of glycogen
 Building block of disaccharides and polysachharides
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Important monosaccharides Cont...

A 5% (m/v) glucose solution is often

used in hospitals as an intravenous
source of nourishment for patients
who cannot take food by mouth

The body can use it as an energy

source without digesting it

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 Important monosaccharides Cont.…
 Glucose is the building unit and end product of hydrolysis of
starch, dextrin, glycogen, sucrose, maltose and lactose.

 It is the major blood and body sugar; all monosaccharides ingested

may be converted into glucose in the body and all can be
synthesized from it, since mainly absorbed into the blood stream or
into which it is converted in the liver is glucose

 Inborn and acquired impairment of glucose metabolism is

associated with a number of human diseases, such as diabetes
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mellitus, glycosuria etc...
 Important monosaccharides Cont.….
 Fructose
Dietary sources: fruit juices, honey and sugar cane.
 Sweetest sugar and is reducing keto-sugar
 It is called the semen sugar, since it is present is seminal
fluid and is the source of energy for the spermatozoa
In the seminiferous tubular epithelial cells, fructose is
formed from glucose
It is obtained from inulin and sucrose hydrolysis.
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 Important monosaccharides Cont.…

 GALACTOSE

Dietary source: diary products

 less sweet than glucose
 used in the synthesis of milk sugar in mammary glands

 It is a constituent of glycolipids and glycoproteins

 It is required for the development of brain and nervous
tissue in infants.
Inborn errors of its metabolism are connected with the
disease known as galactosemia.
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 Important monosaccharides

 MANNOSE

 Mannose is a subunit in glycoproteins and neuraminic acid

 It is obtained by hydrolysis of the plant mannosans and gums

 It does not occur free in nature

 In the human body, it is found as a constituent of

glycoproteins

 Its reduction product that is mannitol is important clinically in

cerebral edema.
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 Important monosaccharides

 D-glyceraldehyde and dihydroxyacetone are aldo- and keto-

trioses, respectively, that are intermediary compounds in
carbohydrate in the process of glycolysis and lipid metabolism

D-Ribose is the most important pentose obtained from Nucleic

acids hydrolysis, component of RNA, DNA, ATP, GTP etc. and a
number of coenzymes. It is a reducing aldo-sugar synthesized in
the body from glucose.
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 Structure of monosaccharide

Fisher Haworth X-ray

projection projection diffraction
• The straight • Cyclic analysis
chain formula or • Boat and chair
structural ring form
formula structure

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Three Representations of Glucose Structure

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 Straight chain

Ring structure

Chair form

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39
 Cyclic Structures of monosaccarides

Monosaccharides of five, six or seven carbons are often more stable

in aqueous solution as cyclic structures than they are as open chains.

Cyclic monosaccharides form spontaneously through a covalent

linkage of the carbonyl carbon with a hydroxyl group in the same
molecule/ intramolecular reaction

The formation of these ring structures is the result of:

 The aldehyde or ketone group spontaneously reacts with alcohol

groups on the 4th or the 5th downstream carbon to form an intramolecular
 Hemiacetals or Hemiketals
 Which contain an additional asymmetric carbon atom;
 Anomeric carbon 40
Hemiacetal & Hemiketal formation
An aldehyde can react with an alcohol to form Hemiacetal

A ketone can react with an alcohol to form  Hemiketal

41 41
42
43
 Isomerism
of
Carbohydrate

44
 Physical Properties of Monosaccharides

1. Isomerism
• The compounds possessing identical molecular
formula but different structures are called
isomers.

Various types of isomerism

1. Structural isomerism
2. Stereoisomerism

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 Structural isomerism
• Same molecular formula but differ from each other by distribution
of the atoms into functional groups
• Functional group isomerism:- Isomers that have the same carbon
skeleton but differ in the nature of the main functional group, e.g.,
aldo-/keto- isomers such as glucose and fructose.

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Ring isomerism: Isomers that differ only in the nature of
their ring forms, e.g., pyran/furan forms of the same sugar,
such as glucopyranose and glucofuranose.

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 Stereoisomerism

• Same molecular formula and same structure but they

differ in spatial arrangement of these groups around
their similar carbons or differ only in the three-
dimensional orientations of their atoms in space.

• That is arrangement of their atoms in space.

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 Stereoisomerism

• There are four types of stereoisomers that can be

associated with glucose are

D and L isomerism
Optical isomerism
Epimerism
α and β anomerism

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 Asymmetric carbon atom
• Asymmetric carbon means that four different groups
are attached to the same carbon.

• The reference molecule is glyceraldehyde which has

a single asymmetric carbon atom.

• The number of possible stereoisomer depends on

the number of asymmetric carbon atoms by the the
Vont Hoff’s rule, i.e., "2n“ formula where n is the
number of asymmetric carbon atoms.

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 Reference Carbon Atom of Sugars

• All monosaccharide can be considered as molecules

derived from glyceraldehyde by successive addition of
carbon atoms. Therefore, penultimate carbon atom is the
reference carbon atom for naming the mirror images

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 D and L isomerism (ENANTIOMERS)

• A special type of isomerism found in pairs of structures

that are mirror images of each other. The mirror
images are termed as enantiomers and the two members
are designated as D- and L- sugar.

• D-sugars are naturally occurring sugars and body can

metabolize only D-sugars and L-sugars are not
metabolize in our body.

• D-glucose is dextrorotatory. In clinical practice, it is

often called as dextrose

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D and L isomerism

53
 Enantiomers vs diastereomers
• Enantiomers: stereoisomers that are mirror images
– example: D-erythrose and L-erythrose are
enantiomers
• Diastereomers: stereoisomers that are not mirror
images
– example: D-erythrose and D-threose are
diastereomers

Mirror Mirror
plane plane

CHO CHO CHO CHO

H OH HO H HO H H OH
H OH HO H H OH HO H
CH2 OH CH2 OH CH2 OH CH2 OH
D-Erythrose L-Erythrose D-Threose L-Threose 54
 Anomerism
• These are isomers obtained from the change of position of
hydroxyl group attached to the anomeric carbon after 1st
carbon in mono saccharide, aldehyde group is condensed
with the hydroxyl group of the 5th carbon to form ring.

• These are isomers that differ in distribution of H and OH

groups around the asymmetric anomeric carbon atom after
cyclization of the molecule

• e.g.  and  glucose are 2 anomers, also  and  fructose are

2 anomers.
• Glucose exists in biological systems not as a rectangle, but as
a pyranose ring.
•  -D-glucopyranose is the predominant form
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 Epimerism
• Epimerism is the stereoisomerism if two
monosaccharides differ from each other in their
configuration around a single specific
carbon(other than anomeric) atom.

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 Geometric isomers

These are isomers that differ in distribution of atoms or

groups around the axis of a double bond in space,
It is differ by position of the hydroxyl group on one or more
of their asymmetric carbons in Glucose.
e.g., cis-form of a compound that has groups on the same side
of the double bond and trans-form that has the groups on
opposite sides of the double bond.

HOOC C H HOOC C H

HOOC C H H C COOH
Malate (cis-isomer) Fumarate
Cis-fumaric acid (trans-isomer)acid
Trans-fumaric
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 2. Optical isomerism
• Optical activity is the capacity of a substance to rotate the plane
polarized light passing through it.
• The presence of asymmetrical carbon atom causes optical activity.
When a beam of plane-polarized light is passed through a solution
of carbohydrates, it will rotate the light either to right or to left.
Clockwise direction
• Dextrorotatory(d) or (+), glucose, galactose and starch

Counterclockwise direction
• Levorotatory(l)or (-), fructose and invert sugar

Equal direction ( No net rotation)

• Racemic mixture
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Optical isomerism

59
 Mutarotaion
• Mutarotaion is defined as the change in the specific
optical rotation by the interconversion of α and β forms
of D glucose to an equilibrium mixture

• It is the spontaneous change in the specific degree of

optical rotation of a freshly prepared sugar solution -
particularly in dilute alkaline solutions.

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 Mutarotaion

Eg. freshly prepared -glucose has a specific rotation of +112 that

decreases gradually till it stabilizes at +52.5. Similarly, freshly
prepared -glucose has a specific rotation of +19 that gradually
increases till getting stabilized at +52.5, known for glucose.

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 Chemical Properties of Monosaccharides

A. Susceptibility to oxidation:

Oxidation of the aldehyde and/or the terminal alcoholic groups of

monosaccharides results in production of the corresponding sugar
acids.

Enzymatically, the sugar-acids are produced by dehydrogenases using

NAD+ or NADP+ as coenzymes in our body.

62
There are 3 types of Sugar acids depending on nature of the
oxidized group

1. The aldehyde group is oxidized into an aldonic acid catalyzed

by a specific dehydrogenase or a mild oxidizing reagent, such
as bromine water and O2.
Examples: glyceraldehyde gives glyceric acid, glucose gives
gluconic acid and galactose gives galactonic acid

63
2. The terminal -CH2OH group is oxidized into uronic acid catalyzed
by a specific dehydrogenases or a moderate oxidizing reagent such as
H2O2 or diluted HNO3. Dehydrogenase catalyzed oxidation of terminal
CH2OH group of glucose is common in the liver.

CH2OH COOH
O O
H H H H
H H
OH H OH H
OH OH
OH OH
H OH H OH
-D-Glucose -D-Glucuronic acid

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 Biomedical importance of D-Glucuronic acid

 In the body D-Glucuronic acid is formed from Glucose

in liver by uronic acid pathway, an alternative pathway
for glucose oxidation.

 It is of importance in that it conjugates toxic substances,

drugs, hormones and even bilirubin (a break down product
of Hb) and converts them to a soluble non-toxic substance,
a glucuronide, which is excreted in urine.

65
3. Both of the aldehyde and the terminal -CH2OH groups are
oxidized into a saccharic acid/aldaric acid catalyzed by a strong
oxidizing reagent, such as concentrated nitric acid..

For example glucose gives water-soluble glucaric acid and, galactose

gives the water-insoluble galactaric acid (or mucic acid).

This reaction can be used to differentiate between glucosuria

(presence of glucose in the urine as in diabetes mellitus) and
galactosuria (presence of galactose or lactose in the urine as in
pregnancy and galactose intolerance)

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 Oxidation to Produce Acidic Sugars

Weak oxidizing agents, such as Tollens and Benedict’s solutions,

oxidize the aldehyde end of an aldose to give an aldonic acid

Tollens solution, glucose reduces Ag+ ion to Ag, and with

Benedict’s solution, glucose reduces Cu2+ ion to Cu+ ion
A reducing sugar is a carbohydrate that gives a positive test with
Tollens and Benedict’s solutions 67
 Oxidation to Produce Acidic Sugars

• Tollens and Benedict’s solutions can be used to test for glucose in

urine, a symptom of diabetes.
• Using Benedict’s solution, if no glucose is present in the urine (a
normal condition), the Benedict’s solution remains blue.
• If the presence of glucose is indicated in urine it can form a red
precipitate

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 B. Reduction to Produce Sugar Alcohols
 The carbonyl group present in a monosaccharide (either an aldose
or a ketose) can be reduced to a hydroxyl group using hydrogen
(H2SO4).
• D-Glucose yields D-Sorbitol by tissue specific sorbitol reductase enzyme
• D-Galactose yields D-Dulcitol.
• D-Mannose yields D-Mannitol.
• Ketosugar D-Fructose yields D-Mannitol and D-Sorbitol

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 Susceptibility to reduction

D-Glucitol (D-sorbitol) have properties similar to those of the

trihydroxy alcohol glycerol.

 Used as moisturizing agents in foods and cosmetics because of their

affinity for water
 Used as a sweetening agent in chewing gum; bacteria that cause tooth
decay cannot use poly-alcohols as food sources

 It is an intermediate in the conversion of glucose into fructose in the

seminal vesicles for sperm nutrition

 Sorbitol is an abnormal product from the hyperglycemia associated

with diabetes mellitus and its intracellular accumulation causes
cellular damage in the formation of Cataract
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Mannose gives rise to mannitol that is injected intravenously to
reduce intracranial hypertension in cases of meningitis, cerebral
hemorrhage or thrombosis and has been used for the assessment of
kidney function.

Inositol is a hexahydric cyclic sugar alcohol containing 6-OH groups.

Such inositol is present in high concentration in heart and muscle
tissues; therefore, it is called muscle sugar. It is precursor for inositol
triphosphate which is a secondary messenger of hormones

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 Inositol-hexa-phosphate Can Cause Mineral Deficiency

• Bran (outer coat of wheat seeds) contain an inositol-hexa-

phosphate, named phytic acid.

• Phytic acid reacts at the six phosphate groups with several

minerals (e.g., calcium, magnesium and iron) in the intestine
to give un-absorbable insoluble salts that are lost with
stools.

• This leads to deficiency of these minerals in people with

bran-base body weight loss formulas.

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C. Caramelization
It is the reaction of sugars/starch on heating in alkaline
solution that breaks the sugar into small fragments, which
condense to form a yellow/brown material with a
characteristic odor called caramel.

D. Reducing properties of monosaccharides

Monosaccharides and disaccharides with free aldehyde or ketone

group can reduce the cupric salts, bismuth, silver and picric acid.

For example, addition of alkaline CuSO4 (called Fehling’s solution)

to an aldose sugar produces a red cuprous oxide (Cu2O) precipitate
and converts the aldose to an aldonic acid, such as gluconic acid.
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Reaction of Reducing sugar

74
E. Formation of osazone

The C1 and C2 of reducing sugars (mono- and

disaccharides) react with three molecules of phenyl
hydrazine in three steps; condensation, oxidation and
condensation.
This results in the formation of the precipitatable
characteristic osazone crystals that are used to identify
different sugars.
Crystals of glucose, fructose and mannose are of the same
shape, i.e., needle- or broom-shaped because they differ at
C1 and C2; a difference that is cancelled by the
condensation of the two phenyl hydrazine.
Maltose gives rosette-like or star-shaped crystals, whereas,
lactose gives powder puff-or furry-balls-like crystals
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 HC N NH

CHO HC N NH HC N NH

H OH H2O H OH NH2 O H2O N NH

HO H Condensation HO H Oxidation Aniline HO H Condensation HO H
H OH H OH H OH H OH
H OH H OH NH3 H OH H OH
H2N NH H2N NH H2N NH
CH2OH CH2OH CH2OH CH2OH
D-Glucose Phenyl hydrazine D-Glucophenyl Phenyl hydrazine D-Fructophenyl Phenyl hydrazine D-Gluco/Fructosazone
hydrazine hydrazine

needle- or rosette-like or puff-or

broom-shaped star-shaped crystals furry-balls-like crystals
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F. Fermentation of sugars

Saccharomyces Cerevisiae (Baker's yeast) ferments certain D-sugars,

e.g., glucose, mannose, fructose, sucrose and maltose by its complex
enzyme, zymase through a series of biochemical reactions into ethanol
and CO2.
Galactose is weakly fermented, whereas, polysaccharides and lactose
(except after hydrolysis to component monosaccharides), pentoses and
L-sugars are non-fermentable with such yeast
G. Reaction with phosphoric acid

Reaction of phosphoric acids with monosaccharides gives phosphate

esters e.g. glucose gives glucose-6-phosphate and glucose-1-phosphate.
This phosphorylated sugars are important intermediates in carbohydrate
metabolism. Sugar phosphates are the major metabolically active form
of sugars in the body and cell membranes are impervious from them.
77
 Monosaccharide derivatives

• Sugar acids
 Gluconic acid,
 Glucuronic acid,
 Gluccharic acid
• Sugar alcohol
 Sorbitol,
 Mannitol,
• Sugar phosphates
 Glucose 6 phosphate
• Deoxy sugar
 Deoxyribose.
• Amino sugar
 Hexosamines
• Sialic acid
 N acetyl neuraminic acid 78
 MONOSACCHARIDE DERVATIVES

• Sugar acids
• URONIC ACIDS

• It is formed when terminal CH2OH group of a mono sugar is

oxidised
– Important acids in animals – D-glucuronic acid and its
epimer L-iduronic acid
– In liver cells glucuronic acid combines with steroids, certain
drugs, and bilirubin to improve water solubility therby
helping the removal of waste products from the body
– These acids are abundant in the connective tissue
carbohydrate components. 79
 Mono sugar derivatives

• AMINO SUGARS
• Sugars in which a hydroxyl group (common on carbon 2) is replaced
by an amino group an amino sugar is produced.e.g. D-glucosamine
and D-galactosamine

– It is structural components in glycolipids, glycoproteins and

mucopolysaccharides

– N-acetyl neuraminic acid (NANA) is one form of sialic acid that

is classified as a sugar acid which is component of glycoproteins
and glycolipids

– Galactosamine is the major sugar derivative in the cartilage and

bone mucopolysaccharide chondroitin sulfate, and, glycolipids
80
 AMINO SUGARS
 Glucosamine is also called chitosamine, which is sugar derivative in
chitin, the exoskeleton of insects
 It is exists in the N-acetyl glucosamine or sulfated glucosamine forms
particularly in mucopolysaccharides
 Mannosamine is an active component of the structure of some
antibiotics

81
 Blood Types and Monosaccharides
• The N-acetyl derivatives of D-glucosamine and D-galactosamine
are present in the biochemical markers on red blood cells, which
distinguish the various blood types

• Human blood is classified into four types: A, B, AB, and O

• The plasma membranes of red blood cells carry biochemical

markers made up of monosaccharides

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 Mono sugar derivatives

• DEOXYSUGARS

– monosaccharides in which an - H has replaced an – OH

group

– Important sugars: L-fucose (formed from D-mannose by

reduction reactions) and 2-deoxy-D-ribose

– L-fucose – found among carbohydrate components of

glycoproteins, such as those of the ABO blood group
determinates on the surface of red blood cells

– 2-deoxyribose is the pentose sugar component of DNA.

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 IMPORTANCE OF PENTOSES
 D-Ribose is a pentose.
 If carbon 3 and its accompanying —H and —OH groups were
eliminated from the structure of D-glucose, the remaining structure
would be that of D-ribose

ribose: it is a constituent of nucleic acid that is RNA

 2-deoxyribose: it is a constituent of DNA

84
 GLYCOSIDES
• Monosaccharides can be linked by glycosidic bonds (joining of 2
hydroxyl groups of sugars by splitting out water molecule) to
create larger structures.

• Disaccharides contain 2 monosaccharides e.g. lactose

(galactose+glucose); maltose (glucose+glucose); sucrose
(glucose+fructose)

• Oligosaccharides – 3 to 10 monosaccharides units e.g.

glycoproteins

• Polysaccharides – more than 10 monosaccharides units e.g.

glycogen (homopolysaccharide) having hundreds of sugar units;
glycosaminoglycans (heteropolysaccharides) containing a number
of different monosaccharides species.
85
 Glycosides
• The hydroxyl group of anomeric carbon of a carbohydrate can join
with a hydroxyl group of another carbohydrate or some other
compound to form a glycoside and the bond so formed is known as
glycosidic bond.
eg. R-OH + HO-R’ R-O-R' + H2O
 two monosaccharides joined covalently by an O-glycosidic bond,
which is formed when OH of one sugar reacts with that of anomeric
carbon of the other.
The most common glycosidic linkage is between C1 and C4 (14)
Other glycosidic linkages include;16, 13, 12, 11 and
23.
The linkage can be - or β- depending on the type of the anomers
participating in the linkage.
• Glycosidic bond can be N-linked or, O-linked.
86
 Disaccharide: two monosaccharides linked
by a covalent bond

Glucose Fructose

Table sugar is a disaccharide of one

Glucose and one fructose molecule

871
OLIGOSACCHARIDES
Short chain of monosaccharide units (2-
10 units)

Joined together by glycosidic bond

On hydrolysis gives 2-10 molecules of

simple sugars

88
89
 Oligosaccharides

• Within the human body, oligosaccharides are often found

associated with proteins and lipids in complexes that
have both structural and regulatory functions

• Free oligosaccharides, other than disaccharides, are

seldom encountered in biochemical systems.

• Complete hydrolysis of an oligosaccharide produces

monosaccharides, Upon hydrolysis, a disaccharide
produces two Monosaccharides, a trisaccharide three
Monosaccharides, and so on.
90
OLIGOSACCHARIDES

91
 Structure of oligosaccharides
• Disaccharides

Disaccharides

Reducing Nonreducing

Maltose
Lactose Sucrose
Isomaltose
92
 DISACCHARIDES

• These are glycosides formed by the condensation of 2

simple sugars

• If the glycosidic linkage involves the carbonyl groups of

both sugars ( ) the resulting disaccharide is

• On the other hand, if the glycosidic linkage involves the

carbonyl group of only one of the 2 sugars (as in maltose
and lactose) the resulting disaccharide is reducing.

93
 Important sugars of Disaccharides

• LACTOSE
(milk sugar) disaccharide found in milk; composed of one
molecule of galactose and glucose linked through beta (1,4)
glycosidic linkage; because of the hemiacetal group of the glucose
component, lactose is a reducing sugar

It has a free anomeric carbon; therefore, it has - and - anomic

forms
 Lactose, it is non-fermentable because of the -nature of its
glucosidic linkage.
 It is hydrolyzed by HCl or by intestine enzyme, lactase, into
galactose and glucose.
94
 LACTOSE

 Also called milk sugar because it naturally occurs only in milk.

95
Milk Lactose and Baby Food
Lactose is the most suitable sugar as a milk sweetener for baby feeding
because:
I. It has the lowest degree of sweetness that delays loss of the baby
appetite
II. It is non-fermentable and so no gases are produced by the large
intestine bacteria
III. It is a mild laxative and helps preventing constipation;
IV. It is not an irritant to the stomach and helps preventing vomiting;
V. The unabsorbed sugar is used as a fuel for large intestinal bacteria
that produces some vitamins, vitamin K and biotin (a B vitamin)
VI. It facilitates absorption of milk minerals.
96
 Lactose intolerance

• Human mother’s milk obtained by

nursing infants contains 7%–8%
lactose, almost double the 4%–
5% lactose found in cow’s milk

• The digestion and absorption of

lactose are a problem due to lack
of enzyme lactase is called
lactose intolerance.
97
 Lactose intolerance
• Deficiency of lactase can
be caused by  Fullness,
 discomfort,
 a genetic defect,  cramping ,
 physiological decline with  nausea, and
age,
 Diarrhea
 injuries to the mucosa
lining the intestines.
• Bacterial fermentation of the
lactose further along the
• When lactose molecules remain intestinal tract produces
in the intestine undigested, they
attract water to themselves,  acid (lactic acid) and gas CO2,
causing like adding to the discomfort
98
 Galactosemia

• After lactose has been degraded into glucose and

galactose, the galactose has to be converted into glucose
before it can be used by cells.
• In humans, the genetic condition called galactosemia is
caused by the absence of one or more of the enzymes
needed for this conversion.
• In people with this condition, galactose and its toxic
metabolic derivative galactitol (dulcitol) accumulate in
the blood.
• If not treated, galactosemia can cause mental retardation
in infants and even death. 99
 SUCROSE (Non-reducing disaccharides)

 It is common table sugar. Mainly found in

Sugar Cane.
 It has 1,2 glycosidic linkage of two
Monomer Units of Glucose and Fructose
 It is dextrorotatory, but when hydrolyzed
by the intestinal sucrase enzyme or by
HCl, the produced fructose and glucose
mixture is levorotatory because of the
strong levorotation of fructose
It is a fermentable but non-reducing
sugar
Honeybees and many other
 CLINICAL SIGNIFICANCE: insects possess an enzyme
called invertase that
Small amounts of oral sucrose placed in the
hydrolyzes sucrose to invert
infant's mouth reduces procedural pain sugar.
100
101
 MALTOSE
 Maltose consists of an -glucose unit connected to a glucose unit
through -1,4-glucosidic linkage
 It is hydrolyzed into two glucose molecules by HCl or by the intestine
maltase enzyme.
 Produced by partial acid or enzymatic (amylase) hydrolysis of dietary
starch and glycogen.
 baby foods contain maltose because it is easily digested

 Isomaltose: it is similar to maltose except that it has an α-1→6-

glucoside linkage 102
• CELLOBIOSE
 Cellobiose is produced as an intermediate in the hydrolysis of the
polysaccharide cellulose, or It is produced by partial acid hydrolysis
of cellulose

 Which containing two molecules of D-glucose linked by a beta

(1,4) glycosidic bond; it does not occur freely in nature.

 It is non-fermentable, non-digestible (because humans lack an

enzyme that can hydrolyze the -glycosidic linkage of cellobiose
or cellulose fibers.
CH2OH CH2OH
O  O 
H H OH
H
4 1 O
4 H 1
OH H OH H
OH H H
H OH H OH
-D-Glucose -D-Glucose
103
 OLIGOSACCHARIDE SUGARS

• Oligosaccharides are small polymers often found attached

to polypeptides in glycoproteins and some glycolipids.

• They are attached to membrane and secretory proteins

found in endoplasmic reticulum and Golgi complex of
various cells

• Two classes: N-linked and O-linked

104
 POLYSACCHARIDES
polysaccharides

Higher molecular weight of Polymers of monosaccharides

and are the major form of carbohydrates occurring in nature.

May be linear or branched, Contain >10

monosaccharide units per molecule

Sparingly soluble in water

Form colloidal solutions when heated with water

They are not sweetish

105
 POLYSACCHARIDES

• These are formed by the condensation of n

molecules of monosaccharides with the removal
of n-1 molecules of water.

• Since condensation involves the carbonyl groups

of the sugars, leaving only one free carbonyl group
at the end of a big molecule, polysaccharides are
non-reducing.

106
107
CLASSIFICATION OF POLYSACCHARIDES

Classification
according to building
unit of
Homopolysaccharides
One type D-monosaccharides or
D-monosaccharide derivatives

Polysaccharides
Heteropolysaccharides
Different type of D-monosaccharides

108
 Homopolysaccharides Heteropolysaccharides

Two monomer Multiple

types, monomer
unbranched types,
Unbranched Branched branched

109
Homopolysaccharides

• Several units of one and the same

type of monosaccharide unit

Starch
Dextrins
Glycogen
Cellulose
Inulin
110
 Homopolysaccharides
Starch:
It is homopolysaccharides and the major storage and
nutritional form of plant carbohydrates in cereals.
e.g., wheat, rice, potatoes, sweet potatoes, nuts and vegetables.

 Homopolymer composed of D-glucose units held by 1,4-α -

glycosidic bonds.

Starch granules are composed of two types of polysaccharides

 Amylose (15-20%) and
 Amylopectin (80-85% ) 111
 Starch Homopolysaccharides

Amylose - The core of the granule is composed of the unbranched

helical chains of 200 to 20 000 -glucose units linked through -1,4-
glucosidic linkages and represents 20% of the granule.
It is inner part of water soluble

Amylopectin – It is made up of the branched of -glucose units linked

through -1,4-glucosidic linkages in straight chains and through -
1,6-glucosidic linkages at the branch points and representing 80% of the
granule.
It is outer part of water insoluble

Contains few thousand glucose units looks like a branched

tree (20-30) glucose units per branch
112
 CH2OH CH2OH
Starch granule O O
H H H H
H
Amylose 4 1 4H 1
OH H OH H
O  O  O
H OH H OH n
CH2OH CH2OH
O O
Amylopectin H H H H
4H 1 4
H
1
OH H OH H
O  O 
O
H OH H OH
CH2OH CH2OH CH26 CH2OH
O O O O
H H H H H H H H
H
4 1 4H 1 4H 1 4H 1
OH H OH H OH H OH H
O  O  O  O  O
H OH H OH H OH H OH n
113
 Amylose
1) Soluble in water
2)Gives Blue colour with dilute
iodine solution
3)Structure –unbranched
4)250 to 300 D-glucose units
linked by alpha 1→4 linkages
5)Mol. wt approx.60000
6)Occurs at the extent of 15 to
20%
Amylopectin
1)Insoluble in water
2)Gives reddish colour with
iodine solution
3)Structure – highly branched
4)Units joined together
by Alpha 1→4glycosidic bond
and at branch point with alpha
1→6 glycosidic linkages
5)Mol. wt. approx 500000
6)0ccurs at 80 to 85%
114
 Dextrins
 Dextrins are a group of low-molecular-weight carbohydrates
produced by the hydrolysis of starch or glycogen.

 Dextrins are mixtures of polymers of D-glucose units linked by

α-(1→4) or α-(1→6) glycosidic bonds.

 Starch is hydrolyzed by HCl or salivary and pancreatic

amylases into glucose and maltose .

 The various intermediate are soluble starch, amylopectin,

erythrodextrin and achrodextrin.

 Dextrins are often referred to as either amylodextrins,

erythrodextrins or achrodextrins
115
 Uses of Dextrin

fig 2-

Used in infant formulas (prevent the coagulating of milk in baby’s

stomach)

-Indigestible dextrin are developed as soluble fiber supplements for

food products
- Also Used as thickening agents in food processing

116
 Uses of Dextrans
• Promotes Healthy Intestinal Flora

• Dextrin is considered a prebiotic, compounds that feed probiotics or

“good” bacteria. It has been shown to aid lactobacilli, a powerful
beneficial bacteria responsible for supporting digestion. As the
good bacteria continues to proliferate throughout the digestive
system, a balanced ratio of good to bad bacteria is established.

• Supports Healthy Cholesterol Levels

• Dietary fiber has been shown to reduce “bad” cholesterol (LDL)

levels to support cardiovascular health. As a dietary fiber, dextrin is
no exception and has been shown to reduce triglyceride
levels. Triglycerides are fats in the blood that have the ability to
increase heart disease and stroke risk. Although it may lower LDL
levels, dextrin may help maintain HDL levels, or the “good”
cholesterol.
117
 Uses of Dextrans
Supports Healthy Blood Sugar
• Dextrin, along with all dietary fibers, may aid in reducing the glycemic load
of a meal containing carbohydrates.
• Although it is fiber of a carbohydrate, it is not digested and does not raise
blood sugar or insulin.
Supports Heart Health
• The cholesterol- and triglyceride-lowering effects of dextrin make it an
excellent dietary addition for supporting heart health. The compound may
provide support for the heart and blood vessels, an action that may lower the
risk for heart disease.
Relieves Occasional Constipation
• In general, fiber provides bulk in the intestines and allows for the
elimination of wastes out of the body via increased bowel movement
frequency.
Provides Satiation and Healthy Weight Loss
• Dextrin may help provide satiation, helping the body feel full and satisfied.
In all its forms, fiber creates more bulk in the stomach and breaks down very
slowly. This feeling of fullness can be very helpful for people who are
wishing to lose weight 118
 Therapeutic Applications of Dextran

 Dextran forms a colloidal solution in water and is used as a

plasma substitute to restore blood pressure in cases of
hemorrhagic shock.

 It stays in plasma for a longer time and retains intravascular

water to maintain plasma volume.

 Dextran ferrous sulfate is a suitable form for intramuscular

injection of iron for treatment of iron deficiency anemia.

 Sodium dextran sulfate is an anticoagulant.

119
 Glycogen
 Glycogen is the storage form of carbohydrate in
animal or it is Animal starch.
• It is stored in muscle and in liver
 Glucose is the repeating unit in glycogen joined together
by α(1-4) glycosidic bonds, and α(1-6) glycosidic bonds
at branching points at every 8 to 12 glucose unit.
 Complete hydrolysis yields glucose
 Hydrolyzed by both α and β-amylases and by glycogen
phosphorylase
• The interior core portion contains a primer molecule
known as glycogenin

120
 Glycogen
The glucose storage polymer in animals, is similar in
structure to amylopectin
 But glycogen has more a(16) branches.

• The highly branched structure permits rapid glucose release from

glycogen stores, e.g., in muscle during exercise.

• In the liver, glycogen synthesis and degradation are regulated to

maintain blood-glucose levels as required to meet the needs of the
organism as a whole.

121
 Glycogen
• Glycogen serves as a buffer to maintain blood glucose level.

• In contrast, in muscle, these processes are regulated to meet the

energy needs of the muscle itself.

• The concentration of glycogen is higher in the liver than in

muscle (10% versus 2% by weight), but more glycogen is
stored in skeletal muscle overall because of its much greater
mass.

122
 CH2OH CH2OH
H O O
glycogen
H H H
H H
OH H OH H 1
O
OH
O
H OH H OH

CH 2OH CH2OH 6 CH2 CH2OH CH2OH

H O H H O H H 5 O H H O H H O H
H H H H H
OH H OH H 4 OH H 1 4 OH H OH H
O O O O OH
OH 2
3
H OH H OH H OH H OH H OH

123
 CELLULOSE

 Most abundant of all carbohydrates and it is a polymer of

glucose
 It is made up of glucose units combined with beta-1,4
linkages
 It has a straight line structure, with no branching points.
• Insoluble, chemically very resistant.
• Major structural material of plants, wood, cotton.
• It is a major constituent of fiber.
• Cellulose is totally absent in animal.

 On heating with high concentrations of acids yields

disaccharide Cellobiose and D-glucose. 124
 Cellulose
 Herbivorous animals utilize cellulose with the help of
bacteria.
 Human beings lack Cellulase enzyme that hydrolyzes
the β (1→ 4) bonds, and so cannot digest cellulose. It is
an important source of "bulk" in the diet, and the major
component of dietary fiber stimulating peristalsis and
elimination of indigestible food residues.

125
 Chitin

CH2OH CH2OH
O O
H H H H
O 4 1 O 4 1 O
OH H OH H
2 2
H HN C CH3 H HN C CH3
O O n
-D-2-N-Acetyl-glucosamine -D-2-N-Acetyl-glucosamine

126
Inulin (Fructosan) Storage polysaccharide

127
Uses of Inulin

128
Heteropolysaccharides

• Two or more different types of

monosaccharide units or their
derivatives

Heteropolysaccharides

Plant Human
Heteroglycans Glycosaminoglycans

Agar Heparin
Gum Chondritin sulfate
Pectin Hyaluronic acid

129
Heteropolysaccharides

They provide protection, shape, extracellular support, or site of

recognition for the cells.

They are of two types Heteropolysaccharides

A. Non-nitrogenous heteropolysaccharides:
B. Nitrogenous heteropolysaccharides:

A. Non-nitrogenous heteropolysaccharides:
They do not contain sugaramines.
Plant gums, mucilages, and Pectins

 Composed of pentoses, hexoses and uronic acids

 Used as emulsifying agents and for the treatment of diarrhea.
130
Agar (Galactosan)

131
 HETEROPOLYSACCHARIDES
B. Nitrogenous heteropolysaccharides: contain sugar amines.
Proteoglycans, glycoproteins, and glycolipids
• Glycosaminoglycans or mucopolysaccharides forming the
proteoglycans are the most abundant heteropolysaccharides in the
body.
• They are long unbranched molecules containing a repeating
disaccharide unit.
• Usually one sugar is an uronic acid (either D-glucuronic or L-
iduronic acid) and the other amino sugar is either (mainly, N-
Acetylglucosamine or N-acetylgalactosamine)
• Thus GAGs are a polymer of [uronic acid-amino sugar]n
• One or both sugars contain sulfate groups (exception is hyaluronic acid).
• GAGs are highly negatively charged what is essential for their function. 132
133
 Occurrence of GAGs
• Proteoglycans are found in the:

a) Synovial fluid of joints

b) Vitreous humour of the eye
c) Arterial wall
d) Bones
e) Cartilage

134
 Functions of GAGs

• Major components of the extracellular matrix

• Producing a gel like matrix which functions as
a cushion against mechanical shocks.
• They lubricate joints
• They also give resilience (elasticity) to
cartilage

135
 Types of GAGs

Hyaluronic Condroitin Keratan

acid sulfate sulfate

Dermatin Heparin
Heparin
sulfate sulfate

136
 Hyaluronic acid
Disaccharide unit

• N-acetyl glucosamine-Glucuronic acid

Location

• Synovial fluid, vitreous humour

Function

• Serve as lubricant and shock absorber

• Highly viscous hyaluronic acid solutions serve as lubricants in the
fluid of joints and they are also associated with the jelly-like
consistency of the vitreous humor of the eye. It is also an essential
component of the extracellular matrix of cartilage and tendons, to
which it contributes tensile strength and elasticity as a result of its
strong interactions with other components of the matrix.
137
138
139
Peptidoglycan

They are linear heteropolymer of alternating β-N-acetylglucosamine

and β-N-acetylmuramic acid residues linked by β1-4 bonds.
• Major constituents of bacterial cells wall are heteropolysaccharides
consisting of repeating units of N-acetyl muramic acid and N-acetyl
glucosamine.

• This cross-linked polysaccharide provides mechanical strength.

Synthesis of this complex polysaccharide is blocked by penicillin.

• However, the mammalian lysosomal enzyme lysozyme kills bacteria

by hydrolyzing the β1-4 glycosidic bond.

Penicillin and related antibiotics kill bacteria by preventing

synthesis of the cross-links, leaving the cell wall too weak to resist
osmotic lysis.
140
 Sulfur-containing mucopolysaccharides

 It is composed of sugar units containing sulfated.

 Chondroitin

 Heparin,

 Dermatan, and

 keratan sulfates

141
 Condroitin sulfate
Disaccharide unit

• N-acetyl galactosamine-Glucuronic acid and with repeating units of

glucuronic acid → beta-1,3-N-acetyl galactosamine sulphate →
beta-1, 4

Location

• At sites of calcification in bone , cartilage, connective tissues widely

distributed in, tendons, cornea and skin.

Function

• Provide an endoskeletal structure

• Role in compressibility of cartilages: Chondroitin sulphates and
hyaluronic acid are present in high concentration in cartilages and
have a role in compressibility of cartilage in weight bearing.

142
143
 Keratane sulfate

Disaccharide unit

• Is composed of 6-sulfated N-acetyl glucosamine-Galactose linked

by alternating -1,4 and -1,3-glycosidic linkages, does not
contain any uronic acid.

Location

• Cornea, loose connective tissue, cartilage, bone,and a variety of

horny structures formed of dead cells: horn, hair, nails, and
claws; aggregating with chondroitin sulfates

Function

• Transparency of cornea
144
145
 Heparin
Disaccharide unit

• Heparins are composed of a long repeat of sulfated -glucosamine

and sulfated -L-iduronic acid (or D-glucuronic acid) units linked by
alternating - and -1,4-glycosidic linkages

Location

• Intracellular component of mast cells (a type of leukocyte) of liver,

lungs, thymus, spleen, walls of large arteries, skin and in small
quantities in blood.

Function

• an anticoagulant, Heparin binds with thrombin molecule by

stimulates Conformational change in thrombin, this can increase its
affinity for antithrombin as well as other substrate. The heparin-
antithrombin-thrombin complex prevents blood coagulation.
146
147
Heparitin Sulphate
Isolated from amyloid liver, certain normal tissues such as human and
cattle aorta, and from the urine, liver etc.

This compound has negligible anticoagulant activity.

It seems to be structurally similar to heparin, but has

• Lower molecular weight,

• contain more N-acetylation of the glucosamine and percentage of –
SO4 groups are smaller.
• Unlike heparin, its predominant uronic acid is D-Glucuronic acid.

148
 Dermatan Sulphate
 Dermatan sulfate is composed of sulfated -L-iduronate and 4-
sulfated N-acetyl-galactosamine linked by alternating -1,3 and
-1,4-glycosidic linkages.
 It is located in skin, wall of blood vessels and heart valves.

 Role in sclera of eye: Dermatan sulphate is present in

sclera of the eye where it has an important function in
maintaining overall shape of the eye.

149
150
Glycoproteins Proteoglycans

•Protein •Carbohydrate
component is is major
predominant component
•<4% •>4%
carbohydrate carbohydrate

151
 Proteoglycans
It is a major components of connective tissues (cartilage, joints & bone),
wall of blood vessels, skin, eye, and horny structures in which their
many non-covalent interactions with other proteoglycans, proteins, and
GAGs provide support, strength and elasticity.

152
Fig. Proteoglycan aggregate of the extracellular matrix
Glycoproteins :- Glycoproteins contain covalently linked
oligosaccharides that are smaller but more structurally complex, and
therefore more information-rich, than GAGs.
Can be attached to proteins with one of two configurations:
i) O-linked - carbohydrate bonded to -OH of Ser or Thr
ii) N-linked - carbohydrate linked to –NH2 of Lys or Asn
They are found on the outer face of the plasma membrane, in the
extracellular matrix, and in the blood.
Inside cells they are found in specific organelles such as Golgi
complexes, secretory granules, and lysosomes.

153
 Cont…
• It play important role in cell-cell and cell-matrix
attachment
• Glycoproteins of mucosal epithelium linings
serve as lubricants and protective agents against
pathogens and noxious chemicals
• Membrane glycoproteins are also receptors for
invading viruses and bacteria and immune cell
recognition molecules

154
155
Glycolipids/ Lipopolysaccharides
Are carbohydrate-lipid conjugates in which the
hydrophilic head groups are oligosaccharides, which, as in
glycoproteins, act as specific sites for recognition by
carbohydrate-binding proteins.
Bacterial cell wall lipopolysaccharides and the human ABO
blood group cell membrane antigens are important examples.
O
O O O
GalNAc Ceramide, or,
Gal O
O Protein
NH-C-CH3 GlcNAc NH-C-CH3
OO
O Fuc O
The ABO Group antigen, Type A
O
O O O
Gal Ceramide, or,
Gal O
O Protein
GlcNAc NH-C-CH
OO 3
Fuc O
The ABO Group antigen, Type B
O O O
Gal O Ceramide, or,
Protein
OO
GlcNAc NH-C-CH3
Fuc O
The ABO Group antigen, Type O156
 Carbohydrates as Informational Molecules
Carbohydrates serve as information-rich molecules that guide
many biological processes. Examples include:
1. Create entry mechanisms for microbial pathogens
Some microbial pathogens have proteins called lectins that help
their adhesion to host cells or toxin entry into cells.
1.1 Influenza virus uses its lectin protein, to attach its host cells
through interactions with oligosaccharides displayed on the host
cell surface.
After initial binding of the virus to a sialic acid–containing
oligosaccharide on the host surface, a viral
sialidase/neuraminidase removes the terminal sialic acid residue,
triggering the entry of the virus into the cell.
Inhibitors of this enzyme are used in the treatment of influenza.
157
1.2 Helicobacter pylori bacturium responsible for most gastric
ulcers, binds to the inner surface of the stomach by
interactions b/n bacterial membrane lectins and specific
oligosaccharides of membrane glycoproteins of the gastric
epithelial cells.

1.3 Cholera toxin (caused by Vibrio cholerae) triggers

diarrhea after entering intestinal cells responsible for water
absorption from the intestine. The entry mechanism is
similar to the above examples.

158
2. Asialoglycoprotein -receptor interactions
The residues of Neu5Ac (a sialic acid) situated at the ends of the
oligosaccharide chains of many plasma glycoproteins protect those
proteins from uptake and degradation in the liver.
Removal of the sialic acid residues by the enzyme sialidase
(neuraminidase) is one way in which the body marks
“old/unwanted” glycoproteins for destruction and replacement.
The plasma membrane of hepatocytes has lectin molecules
(asialoglycoprotein-receptors) that specifically bind
oligosaccharide chains with galactose residues no longer
“protected” by a terminal sialic acid.
This asialoglycoprotein- lectin interaction triggers endocytosis and
destruction of the particular glycoprotein by liver cells.
This mechanism is responsible for removing old RBCs, unwanted
hormones, antibodies & the like from the blood. 159
3. Movement of immune cells (T lymphocytes)
through the capillary wall, from blood to tissues, at
sites of infection or inflammation: At an infection site,
P-selectin (a type of lectin) on the surface of capillary
endothelial cells interacts with a specific
oligosaccharide of the glycoproteins of circulating T
cells.
4. Interaction of sperm with ovulated eggs
Through hyaluronidase, allowing sperm entry.

160
Fig. carbohydrate residues that serve as high affinity binding sites

161
Reference • Textbook of biochemistry, for medical
students 6th edition, dm vasudevan,
sreekumari s, kannan vaidyanathan
• Textbook of Medical Biochemistry,8th
edition, Dr (Brig) MN Chatterjea,
Rana Shinde
• General, Organic, and Biological
Chemistry,5th edition , H. STEPHEN
STOKER
• Text book of Medical Biochemistry,

162
163