Biochemistry

Power to Understand What We

Are!!

Tensae Gebru (M.Sc)

Dep’t of Med.
Biochemistry,
 Learning objectives
At the end of this session the students will be able to:-

• List the major chemical elements of life

• Explain the significance non-covalent interactions.

• Discuss the properties and role of water.

• Explain the roles of carbohydrates and is

classification.
 Outline
• Common elements of life

• Important functional groups and non-covalent

interactions.

• Water and acid base properties, buffers

• Carbohydrate structure: monosaccharides,

sugar derivatives and disaccharides
 Organization of Life
• elements
• simple organic compounds (monomers)
• macromolecules (polymers)
• supramolecular structures
• organelles
• cells
• tissues
• organisms
Elements:
– Substances that can not be broken down into
simpler substances by chemical reactions.
– There are 110 different elements that are known to man.
• Life requires about 25 of them.

• The living matter is composed of mainly six elements-Carbon,

Hydrogen, Oxygen, Nitrogen, Phosphorus and Sulphur.
(CHONPS).
– These elements together constitute about 90% of the dry
weight of the human body.

• Several other functionally important elements are also found in

the cells.
 These include- Ca, K, Na, Cl, Mg, Fe, Cu, Co, Zn, F, Mo and Se.
 Carbon-a unique element of life
• Carbon is the most predominant and versatile
element of life.

• It possesses as unique property to form infinite

number of compounds.

• This is attributed to the ability of carbon to form:

 stable covalent bonds and C-C chains of unlimited length.

• It is estimated that about 90% of compounds found

in living system invariably contain carbon.
Biomolecules are
compounds of
carbon with a
variety of
functional groups
Functional groups play pivotal role in chemical & physical
properties of organic molecules.
Compounds that are made up solely of carbon and
hydrogen are not very reactive.
Functional groups:
– One or more H atoms of the carbon skeleton may be replaced by
a functional group.
– Groups of atoms that have unique chemical and physical
properties.

• Usually a part of molecule that is chemically active.

• Similar activity from one molecule to another.
• Together with size and shape, determine unique bonding and
chemical activity of organic molecules.
Functional Groups Determine Chemical &
Physical Properties of Organic Molecules

Four Important Functional Groups:

• Hydroxyl (-OH)
• Carbonyl (=C=O)
• Carboxyl (-COOH)
• Amino (-NH2)
– Notice that all four functional groups are polar.
Types of biomolecules
 Small molecules:
 Lipid, phospholipid, glycolipid, sterol,
 Vitamin
 Hormone, neurotransmitter
 Carbohydrate, sugar
 Monomers:
 Amino acids
 Nucleotides
 Monosaccharides
 Polymers:
 Peptides, oligopeptides, polypeptides, proteins
 Nucleic acids, i.e. DNA, RNA
 Oligosaccharides, polysaccharides (including
cellulose)
Structural hierarchy in the molecular organization of cells

Just like cells are building blocks of tissues, biomolecules are

building blocks of cells.
 Making and Breaking Polymers

 There are two main chemical mechanisms in

the production and break down of
macromolecules.
 Condensation or Dehydration Synthesis
 Hydrolysis

 In the cell these mechanisms are regulated

by enzymes.
Relatively few monomers are used by cells to
make a huge variety of macromolecules

Macromolecule Monomers or Subunits

1. Carbohydrates 20-30 monosaccharides
or simple sugars

2. Proteins 20 amino acids

3. Nucleic acids (DNA/RNA) 4 nucleotides (A,G,C,T/U)

4. Lipids (fats and oils) ~ 20 different fatty acids

and glycerol.
Similarities among all types of cells
 All cells use nucleic acids (DNA) to store
information
 Except RNA viruses, but not true cells
(incapable of autonomous replication)
 All cells use nucleic acids (RNA) to access
stored information
 All cells use proteins as catalysts (enzymes) for
chemical reactions
 A few examples of RNA based enzymes, which may
reflect primordial use of RNA
 All cells use lipids for membrane components
 Different types of lipids in different types of cells
 All cells use carbohydrates for cell walls (if
present), recognition, and energy generation
Chemical composition of a normal man
(weight 65 kg)

Constituent Percent (%) Weight (kg)

Water 61.6 40

Protein 17.0 11

Lipid 13.8 9

Carbohydrate 1.5 1

Minerals 6.1 4
Water: The Ideal Compound for Life

– Living cells are 60-90% water

– Water covers 3/4 of earth’s surface

– Water is the ideal solvent for chemical

reactions

– On earth, water exists as gas, liquid, and

solid
 Water
• Making up 60% or more of the weight of most organisms.

• Biological macromolecules assume specific shapes in

response to the chemical and physical properties of water.

• Biological molecules undergo chemical reactions in an

aqueous environment.
• Many of the weak interactions within and between
biomolecules are strongly influenced by the solvent properties
of water.

• Even water insoluble components, such as membrane lipids,

interact with each other in ways dictated by the polar
properties of water.
 …cont’d
 Water is a key reactant in many reactions, usually in
the form of H+ and OH- ions.

 Water is needed not only for biochemical reactions,

but also for:
transporting substances across membranes,
maintaining body temperature,
dissolving waste products for excretion and
producing digestive fluids.
 …cont’d
• No other substance on earth is as abundant as
water.

• It is water that had conditioned our climate.

• The water in oceans, seas and the atmosphere

(vapour) acts as an accumulator of heat.

• In hot weather, it absorbs heat and in cold, it

gives up heat; thus, it keeps the planet warm.
 …cont’d
• In human adults also, total body water accounts for
about 60% of the lean body mass.

• Variations observed are mainly due to differences in fat

contents.

• About 2/3 of this water is within body cells

(intracellular fluid), fluid inside the cells.

• The remaining 1/3 is between cells and in blood

plasma (extracellular fluid) i.e. in the spaces outside the
cells or (plasma and interstitial fluid)
 …cont’d
i.e.
• Two-thirds of this water (28 L in a typical normal 70-
kg person) is intracellular fluid.

• The remaining one-third (14 L) is extracellular and

– 80 % of this is interstitial fluid (11 L) and
– 20 % (3 L) is plasma.

• Extracellular fluid exists in two locations:

surrounding cells ( interstitial fluid) and
inside blood vessels( plasma).
Fig.2 Fluid compartments of the body.
Volumes are for an average 70-kg person.
 Functions of Water in Human Body

• Transports nutrients and oxygen into cells

• Regulates body temperature

• Detoxifies

• Moisturizes the air in lungs

• Helps with metabolism

• Protects vital organ
• Helps organs to absorb nutrients
24
 Water As A Lubricant
• Water is an effective lubricant around joints
• It also acts as a shock absorber for eyes,
brain, spinal cord and even for the foetus Synovial
through amniotic fluid Fluid
• When bones meet at a joint, a fluid between
the bones is required to prevent scraping
against each other
• That fluid is called a synovial fluid, which is
made mainly of water
• Many internal organs have fluid around them
to keep them protected, e.g.,
Brain: Cerebro-spinal fluid
Lungs: Pleural Fluid
Eyes: Mix of fluids
25
 Hydrolysis/ Energy Release
• Water is needed to separate (by hydrolysis) a
phosphate group from ATP or GTP to get energy.
• Without water hydrolysis is not possible.

• ATP +H2O = Energy + ADP + Inorganic Phosphate

• GTP +H2O = Energy + GDP + Inorganic Phosphate

• Water is the engine of metabolism.

• Participates in the biochemical break-down of what
we eat. 26
 Variation in Water Levels
Tissue type:
 lean tissues have higher fluid content than fat tissues.
Gender:
 males have more lean tissue and therefore more body
fluid.
Age:
 lean tissue is lost with age and body fluid is lost with it.

NB: Lean tissue is the muscle tissue without fat.

 Water
• A water molecule (H2O), is made up of
three atoms --- one oxygen and two
hydrogen.
 Polarity
• Many of water’s biological functions stem from
its chemical structure.

• Water is a polar molecule

– It has unequal charge distribution that results in
areas of δ- and δ+ charge (δ = partial)
– The oxygen in water is more electronegative than
the hydrogen
• The oxygen nucleus has a greater attraction for electrons
than the hydrogen nucleus, so the oxygen will have a δ-
charge, leaving the hydrogen with a δ+ charge
 Polarity of water causes hydrogen bonding

 Water molecules are held together by H-bonding

 Partially positive H attracted to partially negative O atom.

 Individual H bond are weak, but the cumulative effect of

many H bonds is very strong.

 H bonds only last a fraction of a second, but at any

moment most molecules are hydrogen bonded to others.
Unique properties of water caused by H-bonds
– Cohesion: Water molecules stick to each other. This
causes surface tension.
• Film-like surface of water is difficult to break.
• Used by some insects that live on water surface.
• Water forms beads.

– Adhesion: Water sticks to many surfaces.

Capillary Action: Water tends to rise in narrow tubes.
This is caused by cohesion and adhesion (water
molecules stick to walls of tubes).
Examples: Upward movement of water through plant
vessels and fluid in blood vessels.
http://www.chemistryland.com/CHM107/Water/WaterBeadsOnPlantPlusWaterCharge.jpg
Unique properties of water caused by H-bonds
– Expands when it freezes.
• Ice forms stable H bonds, each molecule is bonded to four
neighbors (crystalline lattice). Water does not form stable
H bonds.
• Ice is less dense than water.
• Ice floats on water.
• Life can survive in bodies of water, even though the earth
has gone through many winters and ice ages
Unique properties of water caused by H-bonds
– Stable Temperature: Water resists changes in
temperature because it has a high specific heat.
• Specific Heat: Amount of heat energy needed to raise 1 g of
substance 1 degree Celsius
– Specific Heat of Water: 1 calorie/gram/oC

• High heat of vaporization: Water must absorb large

amounts of energy (heat) to evaporate.
– Heat of Vaporization of Water: 540 calorie/gram.

• Evaporative cooling is used by many organisms to regulate

body temperature.
– Sweating
– Panting
Unique properties of water caused by its polarity
– Universal Solvent: Dissolves many (but not all)
substances to form solutions.
Solutions are homogeneous mixtures of two or more
substances (salt water, air, tap water).
All solutions have at least two components:
• Solvent: Dissolving substance (water, alcohol, oil).
– Aqueous solution: If solvent is water.

• Solute: Substance that is dissolved (salt, sugar, CO2).

– Water dissolves polar and ionic solutes well.
– Water does not dissolve nonpolar solutes well.
 Solubility of a Solute Depends on its Chemical
Nature
Solubility: Ability of substance to dissolve in a given
solvent.
Two Types of Solutes:
A. Hydrophilic: “Water loving” dissolve easily in water.
• Ionic compounds (e.g. salts)
• Polar compounds (molecules with polar regions)
• Examples: Compounds with -OH groups (alcohols).
• “Like dissolves in like”
B. Hydrophobic: “Water fearing” do not dissolve in water
• Non-polar compounds (lack polar regions)
• Examples: Hydrocarbons with only C-H non-polar bonds, oils,
gasoline, waxes, fats, etc.
ACIDS, BASES, pH AND BUFFERS
A. Acid: A substance that donates protons (H+).
– Separate into one or more protons and an
anion:
HCl (into H2O ) -------> H+ + Cl-

H2SO4 (into H2O ) --------> H+ + HSO4-

– Acids INCREASE the relative [H+] of a solution.

– Water can also dissociate into ions, at low
levels:
H2O <======> H+ + OH-
B. Base: A substance that accepts protons (H+).

– Many bases separate into one or more positive ions

(cations) and a hydroxyl group (OH- ).
– Bases DECREASE the relative [H+] of a solution ( and
increases the relative [OH-] ).
H2O <======> H+ + OH-

Directly NH3 + H+ <=------> NH4+

Indirectly NaOH ---------> Na+ + OH-

( H+ + OH- <=====> H2O )
Strong acids and bases: Dissociation is almost complete
HCl (aq) -------------> H+ + Cl-
NaOH (aq) -----------> Na+ + OH-

– A relatively small amount of a strong acid or base

will drastically affect the pH of solution.

Weak acids and bases: A small percentage of molecules

dissociate at a give time
H2CO3 <=====> H+ + HCO3-
carbonic acid Bicarbonate ion
C. pH scale: [H+]

pH scale is used to measure how acidic a solution is.

– Range of pH scale: 0 through 14.
• Neutral solution: pH is 7. [H+ ] = [OH-]
• Acidic solution: pH is less than 7. [H+ ] > [OH-]
• Basic solution: pH is greater than 7. [H+ ] < [OH-]

– As [H+] increases pH decreases (inversely proportional).

– Logarithmic scale: Each unit on the pH scale represents
a ten-fold change in [H+].
 The Body and pH
Homeostasis of pH is tightly controlled
Extracellular fluid = 7.4
Blood = 7.35 – 7.45
 If pH is < 6.8 or > 8.0 death occurs
Acidosis (acidemia) below 7.35
Alkalosis (alkalemia) above 7.45

42
 The body produces more acids
than bases
• Acids take in with foods.
• Cellular metabolism produces CO2.
• Acids produced by metabolism of lipids and
proteins. CO 2

Volatile acid H2CO3 CO2+ H2O CO2 CO2

H2SO4 H3PO4
Fixed acid Uric acid
Lactic acid
Ketone body
43
 Maintenance of blood pH

• Three lines of defense to regulate the

body’s acid-base balance
– Blood buffers
– Respiratory mechanism
– Renal mechanism

44
45
D. Buffers keep pH of solutions relatively constant
– Buffer: Substance which prevents sudden large changes
in pH when acids or bases are added.

– Buffers are biologically important because most of the

chemical reactions required for life can only take place
within narrow pH ranges.

– Example:
• Normal blood pH 7.35-7.45. Serious health problems will
arise if blood pH is not stable.
 Buffer systems

• Take up H+ or release H+ as conditions

change
• Buffer pairs – weak acid and a base
• Exchange a strong acid or base for a
weak one
• Results in a much smaller pH change

47
 Henderson-Hasselbach Equation

HA = weak acid
1) Ka = [H ][A ]
+ -

[HA] A- = Conjugate base

2) [H+] = Ka [HA]
[A-]
3) -log[H+] = -log Ka -log [HA]
* H-H equation describes
[A-] the relationship between
pH, pKa and buffer
4) -log[H+] = -log Ka +log [A-] concentration
[HA]
5) pH = pKa +log [A-]
[HA]
 …cont’d
• Henderson and Hasselbalch equation is a convenient way of
viewing the relationship between
• pH of a solution and
• relative amounts of conjugate base and acid present.
• When the ratio of [conj base]/[acid] is 1 : 1
– pH equals the pKa of the acid because log 1 = 0, and thus
pH = pKa .
– i.e. a weak acid is 50% dissociated at a pH equal to its pKa.

• If pH is one unit less than pKa :

 the [conj base]/[acid] ratio is 1 : 10, and

• if pH is one unit above pKa :

 the [conj base]/[acid] ratio is 10 : 1.
 …
cont’d
• Most of the metabolic carboxylic acids have pKa ‘s
between 2 and 5, depending on the other groups on the
molecule.
 The pKa reflects the strength of an acid.

• Acids with a pKa of 2 are stronger acids than those with

a pKa of 5 because, at any pH, a greater proportion is
dissociated.
 Principal buffers in blood
in Plasma in RBC

H2CO3 / HCO3- 35% 18%

HHb / Hb- 35%

HPro / Pro- 7%

H2PO4- / HPO42- 5%
Total 42% 58% 51
 Bicarbonate buffer
• HCl + NaHCO3 ↔ H2CO3 + NaCl

• NaOH + H2CO3 ↔ NaHCO3 + H2O

52
 Phosphate buffer
• Major intracellular buffer

• NaH2PO4-Na2HPO4

• H+ + HPO42- ↔ H2PO4-

• OH- + H2PO4- ↔ H2O + HPO42-

53
 Protein Buffers

• Include plasma proteins and hemoglobin

• Carboxyl group gives up H+
• Amino Group accepts H+

54
 2. Respiratory mechanisms
CO2 CO2
• Exhalation of CO2
• Rapid, powerful, but only works with
volatile acids
• H+ + HCO3- ↔ H2CO3 ↔ CO2 + H20

• Doesn’t affect fixed acids like lactic acid

• Body pH can be adjusted by changing rate

and depth of breathing 55
 3. Kidney excretion
• Most effective regulator of pH
• The pH of urine is normally acidic (~6.0)
– H+ ions generated in the body are eliminated by
acidified urine.

• Can eliminate large amounts of acid (→H+)

• Reabsorption of bicarbonate (HCO3-) (←HCO3-)
• Excretion of ammonium ions(NH4+) (→NH4+)
• If kidneys fail, pH balance fails
56
 Rates of correction
• Buffers function: almost instantaneously

• Respiratory mechanisms: take several

minutes to hours

• Renal mechanisms: may take several

hours to days
57
58
 Non covalent bonds in biological
structures
• Non-covalent interactions are weak electrical bonds
between molecules.
• Types of non-covalent interactions are ionic
(electrostatic) bonds, H-bonds, and van der Waals
interactions.
• Non-covalent interactions (1-5 kcal/mol) are typically
~100-fold weaker than covalent bonds .
– Play important roles in protein and nucleic acid stabilization
because they are "collectively strong."

• NB: the hydrophobic effect drives molecular

interactions, but is not a non-covalent bond per se.
While it takes more energy to break ionic bonds in a dry environment,
in living things molecules are in aqueous environments.

Therefore in Biochemistry: Covalent bonds are stronger than Ionic

bonds, and H-bonds are weaker than both.

Keep in mind that in large numbers H-bonds can be strong.

 Ionic Interactions
Ionic interactions occur between cations and anions.

These bonds are non-directional, and strength depends

on the distance of separation (r) according to 1/r2.

Strength also depends on the medium (dielectric

constant), and is less in polar than nonpolar solvents.

Water is effective at screening the electrostatic

interactions between dissolved ions because it has a
high dielectric constant, a physical property that
reflects the number of dipoles in a solvent.
 …cont’d
 Ionic compounds such as NaCl are readily dissolved in water .

 Water molecules hydrate and stabilize Na+ and Cl- ions,

weakening the electrostatic interactions between them and
countering their tendency to associate in a crystalline lattice.

 The resulting increase in entropy (randomness) of the system

is largely responsible for the ease of dissolving NaCl in water.
 Solvation spheres of water molecules surround ions in solutions.

 Water molecules orient so that the negative ends of their dipoles

contact cations and the positive ends contact anions in solution.
 H-bonds
H-bonds are noncovalent interactions occurring
between the H atom of a dipolar molecule such as
water, and the unshared electron pair of another
atom (i.e., O or N).

These bonds represent the primary way in which water

molecules interact with themselves and many types of
biomolecules .

Alcohols, aldehydes, ketones, and compounds

containing N-H bonds all form hydrogen bonds with
water molecules and tend to be soluble in water.
Fig. Biologically important hydrogen bonds
 Importance of Hydrogen Bonds

• Source of unique properties of water

• Structure and function of proteins

• Structure and function of DNA

• Structure and function of polysaccharides

• Binding of substrates to enzymes

• Binding of hormones to receptors

• Matching of mRNA and tRNA

 Hydrogen Bond Directionality and Strength
Hydrogen bonds are highly directional in that strength
depends on the proper alignment of the interacting atoms.

The best alignment occurs when the orbital containing the

unshared electron pair of the acceptor atom is in line
with the covalent bond between the donor atom and H.
o Directionality confers bonding specificity as with the Watson-Crick
hydrogen bonds between the bases of double helical DNA (A-T; G-
C), and results in very precise three dimensional structures for
nucleic acid and protein molecules.
 Van der Waals Interactions
Van der Waals interactions are bonds between
fluctuating, induced dipoles within the electron
clouds of interacting molecules.
These bonds can occur between nonpolar or polar
molecules.

Van der Waals bonds are extremely dependent on the

distance of separation between molecules, and are
significant only when the electron clouds of the
molecules are just touching.
Van der Waals interactions are demonstrated for two
O2 molecules.
Van der Waals Interactions
 The Hydrophobic Effect
• Refers to the association or folding of
nonpolar molecules in the aqueous solution
• Is one of the main factors behind:
– protein folding
– protein-protein association
– formation of lipid micelles
– binding of steroid hormones to their receptors
• Does not arise because of some attractive
direct force between two nonpolar molecules
 The Hydrophobic Effect
The hydrophobic effect refers to the entropy-driven
aggregation of nonpolar molecules in aqueous solution that
occurs to minimize the ordering of water molecules with
which they are in contact.

This is not an attractive force, but rather a

thermodynamically driven process.

 The hydrophobic effect drives:

 the formation of membranes and
 contributes to the folding of proteins and
 the formation of double helical DNA.

 Fig. shows the cage-like structures formed by water molecules

surrounding a nonpolar solute.
The Hydrophobic Effect
Approximate Bond Distance,
Strength, kJ/mole nm

12-30 0.3

20 0.25

<40 -

0.4 – 4.0 0.2

 CARBOHYDRATE: IMPORTANCE

• Most Abundant Class of Biomolecules in Nature.

• Source of rapid energy production
• Structural building blocks of cells
• Components of several metabolic pathways
• Recognition of cellular phenomena, such as cell
recognition and binding (e.g., by other cells,
hormones, and viruses)
• Associated with Pathological Conditions (Diabetes
Mellitus, Lactose Intolerance).
 Functions of Carbohydrates

1) Energy
• glucose fuels the work of most of the body’s cells
– preferred fuel of NERVOUS TISSUE (the brain, nerves) and RED BLOOD
CELLS (RBC)
• excess glucose is stored as GLYCOGEN in liver and muscle tissue

2) Sparing Body Protein

• if diet does not provide enough glucose, then other sources of
glucose must be found
• if carbohydrate intake < 50 - 100 g, body protein will be used to
make glucose
• an adequate supply of carbohydrate spares body proteins from
being broken down to synthesize glucose
75
 …cont’d
3) Preventing Ketosis (Anti-ketogenic)
– carbohydrates required for the complete
metabolism of fat
– incomplete fat metabolism produces KETONES
– an adequate supply of carbohydrate (> 50 – 100 g
per day) prevents KETOSIS

NB: Carbohydrate intake can take place in different

forms like sugar, starch, fibers etc.

76
 DEFINING CARBOHYDRATES
 Carbohydrates or Saccharides (Greek Sakcharon meaning "Sugar")
• Organic compounds composed of Carbon, Hydrogen and oxygen.

• Many Carbohydrates also contain Nitrogen and other elements.

• Carbohydrates derive their name from a Misleading Concept

'Hydrates of Carbon’
• Hydrogen and Oxygen in Carbohydrates were found to be present in the
same proportion as in water. (2:1).(E.g. Glucose C6H12O6
• It is due to this fact that compounds derived their name “Carbon Hydrate”.
 This term is not a perfect derivation as many
carbohydrates do not have the same
proportion as water.
 (E.g. DEOXYRIBOSE ,C5H10O4)

 CHEMICAL DEFINITION OF CARBOHYDRATES

 Carbohydrates are Polyhydroxy ‫بلوهايدروكسيل‬Alcohols

with Carbonyl groups Which May Either Be
Aldehyde (H-C=O) or Keto (C=O) Groups.
 Types of Carbohydrates

Simple Carbohydrates
– monosaccharides
– disaccharides

Complex Carbohydrates
– Oligosaccharides‫قليل السكاريد‬
– polysaccharides
• glycogen
• starches
Fig. examples of an aldose (A)
• Fibers
and a ketose(B) sugar.
 Types of carbohydrates
• Classifications based on number of sugar units
in total chain.
• Monosaccharides - single sugar unit
• Disaccharides - two sugar units
• Oligosaccharides - 3 to 10 sugar units
• Polysaccharides - more than 10 units
• Chaining relies on ‘bridging’ of oxygen atoms
• glycoside bonds
 MONOSACCHARIDES
• Monosaccharides are those carbohydrates which Cannot be
Hydrolyzed further into more simple carbohydrates.
• Thus, they are the Simplest form of Carbohydrates.
• They are further classified on the basis of:
– Aldehyde or Ketone Group:
• Aldomonosaccharides (Aldoses).
• Ketomonosaccharides (Ketoses).
– Carbon Chain Length.
• Trioses.‫تريوسس‬
• Tetroses.‫تروسس‬
• Pentoses.‫بنتوسيس‬
• Hexoses.‫هيكسوسيز‬
• Heptoses.‫هيبتوسيس‬
EXAMPLES OF MONOSACCHARIDES
NO. OF CARBON ALDO KETO
ATOMS

3C TRIOSE GLYCERALDEHYDE DIHYDROXYACETON

E

4C TETROSE ERYTHROSE ERYTHRULOSE

5C PENTOSE RIBOSE, XYLOSE RIBULOSE,

XYLULLOSE

6C HEXOSE GLUCOSE, FRUCTOSE

GALACTOSE,
MANNOSE
 Properties of monosaccharides
1. Optical Isomerism
 All the monosaccharides except dihydroxyacetone contain
at least one asymmetric carbon atom and hence they exhibit
optical isomerism.
D and L-glyceraldehyde ‫غاليسرالداهيد‬are used as parent compounds
to designate all other sugars (compounds) as D or L forms.

CHO CHO
D & L designations are H C OH HO C H
based on the configuration
CH2OH CH2OH
about the single
D-glyceraldehyde L-glyceraldehyde
asymmetric C in
glyceraldehyde.‫يعتمد على ترتيب‬ CHO CHO
‫الكربون الغير متماثل الفردي في الغاليسرالداهيد‬
H C OH HO C H

The lower representations CH2OH CH2OH

are Fischer Projections. D-glyceraldehyde L-glyceraldehyde
 O H O H
C C
‘
H – C – OH HO – C – H
For sugars with more than HO – C – H H – C – OH
one chiral center, D or L H – C – OH HO – C – H
refers to the asymmetric C H – C – OH HO – C – H
farthest from the aldehyde CH2OH CH2OH
or keto group. D-glucose L-glucose

If the hydroxyl group of the highest numbered chiral carbon is

pointing to the right, the sugar is designated as D (Dextro: Latin for
on the right side).

If the hydroxyl group is pointing to the left, the sugar is designated as

L (Levo: Latin for on the left side).

Most naturally occurring carbohydrates are of the D-configuration

 2.Optical Activity
• Monosaccharides except dihydroxy acetone exhibit optical
activity because of the presence of at least 1 asymmetric
carbon atom.

• If a sugar rotates plane polarized light to right then it is called

as dextrorotatory ‫ديكستوراتوري‬and if a sugar rotates the plane
polarized light to the left then it is called as levorotatory.

• Usually ‘+’ sign indicates dextrorotation and ‘–’ sign indicates

levorotation of a sugar.

• Right Rotation (dextrorotatory) E.g. D(+)- Glucose

• Left Rotation (levorotatory) E.g. D(-)-Fructose

 Stereoisomers
• Stereochemistry
• Study of the spatial arrangement of molecules.

• Stereoisomers have
• the same order and types of bonds.
• different spatial arrangements.
• different properties.
• Many biologically important chemicals, like sugars,
exist as stereoisomers. Your body can tell the
difference.
 Stereochemistry
Enantiomers Diastereomers Epimers
O O O O O O
H H H H H H
C C C C C C

HO C* H H C* OH HO C* H H C* OH H C* OH HO C* H

H C* OH HO C* H HO C* H HO C* H HO C* H HO C* H

HO C* H H C* OH H C* OH HO C* H H C* OH H C* OH

HO C* H H C* OH H C* OH H C* OH H C* OH H C* OH

CH2OH CH2OH CH2OH CH2OH CH2OH CH2OH

L-glucose D-glucose D-mannose D-galactose D-glucose D-mannose

•Enantiomers = mirror images

•Pairs of isomers that have opposite configurations at
one or more chiral centers but are NOT mirror images
are diastereomers
•Epimers = Two sugars that differ in configuration at
only one chiral center
Some important monosaccharides

• D-glyceraldehyde Simplest sugar

• D-glucose Most important in diet
• D-fructose Sweetest of all sugars
• D-galactose Part of milk sugar
• D-ribose Used in RNA

note that each is a D- enantiomer

 D-glucose
• Glucose is an aldohexose sugar.‫الدوهيكسوس‬
• Common names include dextrose, grape sugar,
blood sugar.
• brain cells, RBCs and the growing embryo only
utilize glucose as a source of energy. H O
• energy source for cells in the body. C

• building block of disaccharides and H C OH

polysaccharides HO C H
• it is the sugar present in blood.
H C OH

• dietary sources: fruits, vegetables(in the form of H C OH

starch), honey CH OH
2

 normal values
fasting: 70 to 99mg/dl
random: below 140 mg/dl
Disorders associated with glucose
• Diabetes Mellitus

• Glycosuria

Renal sugar threshold

it is the maximum capacity of kidneys to
reabsorb glucose.
 D-FRUCTOSE: IMPORTANCE AND BIOLOGICAL
SIGNIFICANCE
 Dietary sources: fruit juices, honey and sugar cane.

 sweetest sugar

 Seminal fluid is rich in fructose.

 Sperm utilizes fructose for energy

 In the seminiferous tubular epithelial cells, fructose

is formed from glucose.
 D-GALACTOSE: IMPORTANCE AND BIOLOGICAL
SIGNIFICANCE

 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.
 Importance of pentoses
• RIBOSE: it is a constituent of nucleic acid
that is RNA

• 2-DEOXYRIBOSE: it is a constituent of
DNA
 Monosaccharide Derivatives of Biological
Importance
• Oxidation Products (Sugar Acids)

• Reduction Products (Sugar Alcohols).

• Amino Sugars.

• Sugar Phosphates.
 Oxidation Products (Sugar Acids)
• When oxidized under proper conditions, Aldoses
may form three types of acids (Sugar Acids):
– Uronic Acids.
– Aldonic acids.
– Saccharic Acids.
• Type of sugar Acid produced depends on which
carbon is oxidized.
 H-C=O Aldonic Acid
 Oxidation Of Aldose At
H-C-OH COOH
H-C=O Carbonyl Carbon
  (Aldehyde Group)
OH-C-H H-C-OH
  Saccharic Acid
H-C-OH OH-C-H H-C=O
 COOH
 
H-C-OH H-C-OH
 H-C-OH Oxidation Of Aldose
CH2OH  
COOH H-C-OH
At Both Aldehyde &
Terminal Carbons
Oxidation Of Aldose OH-C-H
At Primary Alcohol
 
(Terminal Carbon) CH2OH H-C-OH

Uronic Acid H-C-OH
COOH
 MONOSACCHARIDE DERVATIVES
• Important uronic acids in humans are 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.
Amino Sugar: • Substitution of Amino Group for a
Hydroxyl Group of a Sugar Results in
the Formation of an Amino Sugar.
H-C=O • The Amino Group is attached to
 Carbon 2.
H-C-OH
NH2 • Common Examples of Amino Sugars
 (Aminosaccharides)
OH-C-H – Galactosamine
 – Glucosamine
– common constituents of complex
H-C-OH carbohydrate molecule found
 attached to cellular proteins and
H-C-OH lipids
 – Amino acids are often acetylated
CH2OH e.g. N-acetyl-glucosamine.
 Sugar Alcohols; Reduction Products
• Sugar Alcohols are obtained by reduction of
Monosaccharides (Both Aldoses and Ketoses) and
disaccharides.
• Sugar alcohols, also known as Polyols, Polyhydric
Alcohols, or Polyalcohols.
Sugar Alcohols are the Hydrogenated forms of the
Aldoses or Ketoses
H- C=O + H2 CH2OH
 
H-C-OH H-C-OH


OH-C-H
OH-C-H 

H-C-OH H-C-OH
 
H-C-OH
H-C-OH 
 CH2OH
CH2OH Sorbitol
Glucose
Sugars with their Corresponding Alcohols
Glyceraldehyde & Glycerol
Dihydroxyacetone
Glucose Sorbitol (Glucitol)
Mannose Mannitol
Fructose Sorbitol & Mannitol
Galactose Dulcitol
Ribose Ribitol
Erythrose Erythritol
Xylose Xylitol
Lactose Lactitol
Maltose Maltitol
 Sugar Phosphates
• Phosphate Esters formed by various
Monosaccharides are of Great Importance in
Metabolic Reactions.

• Sugar phosphates of biological importance.

– Ribose and DeoxyriboseDNA in Nucleic Acids are
Phosphate Esters of these monosaccharides.
– Phosphates of Glucose, Fructose and
Glyceraldehyde etc. are important intermediate
compounds in carbohydrate metabolism of almost
all the cells.
Mono sugar derivatives
• DEOXYSUGARS
– monosaccharides in which an - H has replaced an – OH
group
– Important sugars: L-fucose‫( فيوكوز‬formed 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.
 Disaccharides

• Two Joined Monosaccharides.

• Sucrose: Glucose + Fructose
• α, β(1→2).
• Maltose: Glucose + Glucose
• α(1® 4).
• Lactose: Glucose + Galactose
• β (1→4).
 Lactose
• Also called milk sugar because it naturally occurs
only in milk.

• On hydrolysis it yields one molecule of glucose and

one molecule of galactose which are linked together
through 1-4 glycosidic linkage

• Two Monomer Units of Lactose are:-

– Glucose.
– Galactose.
 Biological Significance of Lactose
• Sole source of Carbohydrates in Neonates.
• Absorption of Calcium.
• Source of Galactose (for developing Brain)
• Clinical Aspects.
– Lactosuria (During pregnancy and lactation).
– Lactose intolerance.‫عدم تحمل‬
 LACTOSE INTOLERANCE:

• due to the absence of the enzyme lactase

• undigested lactose leads to bacterial

fermentation‫ تخمر‬in colon and generation
of gases.

• these products cause diarrhea‫اسهال دايريا‬,

bloating and pain in the GIT.

• treatment: formula feed

 Sucrose
 It is common table sugar.
 Mainly found in Sugar Cane.
 It has 1,2 glycosidic linkage.

 Two Monomer Units of Sucrose are:-

Glucose.
Fructose.

 CLINICAL SIGNIFICANCE: Small amounts of

oral sucrose placed in the infant's mouth
reduces procedural pain.
 MALTOSE
 yields upon the hydrolysis of starch(amylase)

 made up of two molecules of glucose

 glycosidic linkage(1,4)

CLINICAL SIGNIFICANCE:
 maltose is digested by the enzyme maltase. baby
foods contain maltose because it is easily
digested.
 OLIGOSAACCHARIDES

 comprised of three to ten

monosaccharides
 example: fructooligosaccharides
 cell membrane proteins contain
oligosaccharides.

 the oligosaccharide units of

glycoproteins are rich in information and
are functionally important.
 References
• Nelson, D. L. And Cox, M.M. (2005). Lehninger
Principles of Biochemistry 5th edition.

• Murray R.K et al. Harper's illustrated Biochemistry 30th

edition .

• Pamela C.C, and Richard A.H., Lippincott's Illustrated

Reviews: Biochemistry 5th edition, J.B.

• Thomas M. Devlin. Text Book of Biochemistry with

Clinical Correlations. 6th Edition, 2006, Wiley-Liss
Publication, USA
,
 (Optional PPTs)
Electron Arrangements of Important Elements of Life

1 Valence electron 4 Valence electrons 5 Valence electrons 6 Valence electrons

III. How Atoms Form Molecules:
Chemical Bonds
Molecule: Two or more atoms combined chemically.
Compound: A substance with two or more elements
combined in a fixed ratio.
• Water (H2O)
• Hydrogen peroxide (H2O2)
• Carbon dioxide (CO2)
• Carbon monoxide (CO)
• Table salt (NaCl)
– Atoms are linked by chemical bonds.
Chemical Formula: Describes the chemical
composition of a molecule of a compound.
– Symbols indicate the type of atoms
– Subscripts indicate the number of atoms
How Atoms Form Molecules: Chemical
Bonds
“Octet Rule”: When the outer shell of an atom is not full,
i.e.: contains fewer than 8 (or 2) electrons (valence e-),
the atom tends to gain, lose, or share electrons to
achieve a complete outer shell (8, 2, or 0) electrons.

Example:
Sodium has 11 electrons, 1 valence electron.
Sodium loses its electron, becoming an ion:
Na -------> Na+ + 1 e-
1(2), 2(8), 3(1) 1(2), 2(8)
Outer shell has 1 e- Outer shell is full
Sodium atom Sodium ion
Number of valence electrons determine the chemical
behavior of atoms.
Element Valence Combining Tendency
Electrons Capacity
Sodium 1 1 Lose 1
Calcium 2 2 Lose 2
Aluminum 3 3 Lose 3
Carbon 4 4 Share 4
Nitrogen 5 3 Gain 3
Oxygen 6 2 Gain 2
Chlorine 7 1 Gain 1
Neon* 8 0 Stable
* Noble gas
How Atoms Form Molecules: Chemical
Bonds
Atoms can lose, gain, or share electrons to satisfy octet
rule (fill outermost shell).

Two main types of Chemical Bonds

A. Ionic bond: Atoms gain or lose electrons
B. Covalent bond: Atoms share electrons