CHAPTER 14

BIOMOLECULES

1
 Introduction
Biomolecules are the most essential organic molecules,
which are involved in the maintenance and metabolic
processes of living organisms. These non-living molecules
are the actual foot-soldiers of the battle of sustenance of
life. They range from small molecules to large
macromolecules like proteins, nucleic acids,
carbohydrates, lipids.

2
 CARBOHYDRATES
Carbohydrates are defined as polyhydroxy
aldehydes or ketones which produces such units on
hydrolysis. carbohydrates as sugars or substances
that taste sweet. They are collectively called as
saccharides.
These have the following basic composition:
Cx(H2O)y and are hydrates of carbon.
Eg: C6H12O6 is C6(H2O)6
 Exception Rhamnose C6H12O5 is also a
carbohydrate but does not fit in the formula.
3
 CLASSIFICATION

 Monosaccharides - simple sugars with multiple OH groups. Can not be

further hydrolysed. Based on number of carbons (3, 4, 5, 6), a
monosaccharide is a triose, tetrose, pentose or hexose.
Eg Glucose, Fructose, Ribose,Galactose

 Oligosaccharides – 2-9 monosaccharide units covalently linked. These

include Disaccharides - 2 monosaccharides covalently linked.
 Eg Sucrose, Lactose, Maltose
 Trisaccharides - 3 monosaccharides covalently linked. Eg Glyceraldehyde
 Tetrasaccharides - 4 monosaccharides covalently linked. Eg Erythrose.

 Polysaccharides - polymers consisting of chains of monosaccharide units.

These are not sweet in taste, Hence also called non-sugars
Eg: Starch,cellulose,Glycogen

4
 Monosaccharides
Aldoses (e.g., glucose) have Ketoses (e.g., fructose) have
an aldehyde group at one end. a keto group, usually at C2.
H O
C CH2OH

H C OH C O

HO C H HO C H

H C OH H C OH

H C OH H C OH

CH2OH CH2OH

D-glucose D-fructose
5
D vs L Designation
CHO CHO
D & L designations
H C OH HO C H
are based on the
configuration about CH2OH CH2OH
the single asymmetric D-glyceraldehyde L-glyceraldehyde
C in glyceraldehyde.
CHO CHO
The lower H C OH HO C H
representations are
CH2OH CH2OH
Fischer Projections.
D-glyceraldehyde L-glyceraldehyde
6
 Sugar Nomenclature
O H O H
For sugars with more C C
than one chiral center, H – C – OH HO – C – H
D or L refers to the HO – C – H H – C – OH
asymmetric C farthest H – C – OH HO – C – H
from the aldehyde or H – C – OH HO – C – H
keto group. CH2OH CH2OH
Most naturally occurring D-glucose L-glucose
sugars are D isomers.

7
Glucose

8
 Preparation of Glucose
From sucrose (Cane sugar):
If sucrose is boiled with dilute HCl or H2SO4 in
alcoholic solution, glucose and fructose are
obtained in equal amounts.
C12H22O11+H2O→C6H12O6+C6H12O6
From starch:
Commercially glucose is obtained by hydrolysis
of starch by boiling it with dilute H2SO4 at 393 K
under pressure.
(C6H10O5)n+n H2O → n C6H12O6
9
 Structure of Glucose
Glucose is an aldohexose also known as dextrose. Its
molecular formula is C6H12O6

10
Glucose is correctly named as D(+) glucose.
‘D’ before the name of glucose represents the
configuration whereas ‘(+)’ represents
dextrorotatory nature of the molecule.

11
Structure elucidationof glucose
When HI is heated for a long time, n-hexane is formed
which indicates that all the six carbon atoms are linked in
a straight chain.

12
The oxime is formed when glucose reacts with
hydroxylamine and cyanohydrins on the addition of
hydrogen cyanide to it. This reaction can confirm the
presence of the carbonyl group in glucose.

13
On the reaction of glucose with a mild oxidising agent
like bromine water, the glucose gets oxidized to a
carboxylic acid that contains six carbon atoms. This
indicates that the carbonyl group is present as
an aldehyde group.

14
Glucose as well as gluconic acid both yields dicarboxylic
acid and saccharic acid on oxidation with nitric acid. The
presence of primary alcohol is indicated by this.

15
The presence of -OH group is confirmed after the
acetylation of glucose with acetic acid which gives
glucose pentaacetate.

16
Structure of Glucose:
These two optical isomers differ in configuration around any
other C atom other than C1 atom.
In D-Glucose, −OH group on first chiral `C’ from the bottom is
on right hand.
In L-Glucose, −OH group points to the left of chiral carbon.

17
Cyclic Structure of Glucose
The structure of glucose explained most of its
properties but the following reactions and facts could
not be explained by this structure.
Despite having the aldehyde group, glucose does not
give 2,4-DNP test, Schiff’s test and it does not form
the hydrogensulphite addition product with NaHSO 3.
The pentaacetate of glucose does not react with
hydroxylamine indicating the absence of free —CHO
group.

18
This behaviour could not be explained by the
open chain structure for glucose. It was
proposed that one of the —OH groups may add
to the —CHO group and form a cyclic
hemiacetal structure. It was found that glucose
forms a six- membered ring in which —OH at
C-5 is involved in ring formation. This
explains the absence of —CHO group and also
existence of glucose in two forms as shown

19
 Cyclic forms of glucose
 The two cyclic hemiacetal forms differ in the configuration of -OH
group at C1 and are called anomeric carbon.
 Such isomer are known as anomers

20
 1
CHO

H C OH
2
HO C H D-glucose
3
H C OH (linear form)
4
Pyranose
H C OH
Structure 5

Of glucose CH2OH
6

6 CH2OH 6 CH2OH
5 O 5 O
H H H OH
H H
4 H 1 4 H 1
OH OH
OH OH OH H
3 2 3 2
H OH H OH
-D-glucose -D-glucose

α-D(+)glucopyranose β-D(+)glucopyranose 21
 Fructose
Fructose is an important ketohexose. It is
obtained along with glucose by the hydrolysis
of disaccharide, sucrose. It is a natural
monosaccharide found in fruits, honey and
vegetables. In its pure form it is used as a
sweetner

22
 Structure of Fructose
Open chain structure
CH2OH

C O

HO C H

H C OH

H C OH

CH2OH

D-fructose
23
Cyclic structure

1
CH2OH

2C O

HO C H
1 CH2OH
3 HOH2C 6 O
H C OH HO
4 5 H 2

H C OH H 4 3 OH
5
OH H
6
CH2OH

D-fructose (linear) -D-fructofuranose

24
It exists in two cyclic forms which are obtained by the addition
of –OH at C-5 to the Carbonyl group. The ring formed is a five
member ring named as furanose with analogy to compound
Furan

25
 Disaccharides
Disaccharides on hydrolysis yield 2 molecules of
same or different monosaccharides
The two monosaccharides are joined together
by an oxide linkage formed by the loss of a
water molecule. Such a linkage between two
monosaccharide units through oxygen atom is
called glycosidic linkage.

26
 Sucrose
The hydrolysis of sucrose by boiling with a mineral
acid, or by the enzyme invertase, produce a mixture of
α-D-(+)-glucose and β-D-(-) fructose.

They are held together by a glycosidic linkage

between C1 of α-glucose and C2 of β-fructose. Since
the reducing groups of glucose and fructose are
involved in glycosidic bond formation, Sucrose is
called a non reducing sugar.

27
28
 Inversion of sugar
Sucrose is dextrorotatory but after hydrolysis
gives dextrorotatory glucose and laevorotatory
fructose. Since the laevorotation of fructose
(–92.4°) is more than dextrorotation of glucose
(+ 52.5°), the mixture is laevorotatory. Thus,
hydrolysis of sucrose brings about a change in
the sign of rotation, from dextro (+) to laevo(–)
and the product is named as invert sugar.

29
 Maltose
Maltose is composed of two α-D-glucose units in
which C1 of one glucose (I) is linked to C4 of another
glucose unit (II).The free –CHO group can be
produced at C1 of second glucose in solution. So it is
a reducing sugar
6 CH 2 O H 6 CH 2 O H

5 O 5 O
H H H H
H H
1 4 1
4 OH H OH H

OH O OH
3 2 3 2

H OH m altose H OH

30
 Lactose
It is more commonly known as milk sugar
since this disaccharide is found in milk. It is
composed of β-D-galactose and β-D-glucose.
The linkage is between C1 of galactose and C4
of glucose. The free –CHO group can be
produced at C1 of glucose in solution. So it is a
reducing sugar

31
32
 Polysaccharides
Polysaccharides contain a large no. of
monosaccharide units joined by glycosidic
linkages
Starch is the main storage polysaccharide of
plants. It is the most important dietary source
for human beings. It is a polymer of α-glucose
and consists of two components— Amylose
and Amylopectin.
33
Amylose is water soluble component which
constitutes about 15-20% of starch. Chemically
amylose is a long unbranched chain with 200-
1000 α-D-(+)-glucose units held by C1– C4
glycosidic linkage.
Amylopectin is insoluble in water and
constitutes about 80- 85% of starch. It is a
branched chain polymer of α-D-glucose held
by C1– C4 and C1-C6 glycosidic linkage.
34
 CH 2 OH 6 CH OH CH 2 OH CH 2 OH CH 2 OH
2
O 5 O H O H O H H O H
H H H H H
H H H H H
OH H 1 4 OH H 1 OH H OH H OH H
O O O O OH
OH 2
3
H OH H OH H OH H OH H OH
a m y lo s e

CH 2OH CH 2OH
H O H H O H amylopectin
H H
OH H OH H 1
O
OH
O
H OH H OH

CH 2OH CH 2OH 6 CH 2 CH 2OH CH 2OH

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

35
 Cellulose
Cellulose occurs exclusively in plants and it is
the most abundant organic substance in plant
kingdom. It is a predominant constituent of cell
wall of plant cells. Cellulose is a straight chain
polysaccharide composed only of β-D-glucose
units which are joined by glycosidic linkage
between C1 of one glucose unit and C4 of the
next glucose unit.

36
 CH2OH 6CH OH CH2OH CH2OH CH2OH
2
O 5 O O H O H O OH
H H H
H H H H H
OH H 1 O 4 OH H 1 O OH H O OH H O OH H
OH H H H
H 2 H
3
H OH H OH H OH H OH H OH
cellulose

Schematic of arrangement of
cellulose chains in a microfibril.

37
 Glycogen
The carbohydrates are stored in animal body
as glycogen. It is also known as animal starch
because its structure is similar to amylopectin
and is rather more highly branched. It is
present in liver, muscles and brain. When body
needs glucose, enzymes break the glycogen
down to glucose. Glycogen is found in yeast
and fungi.

38
Proteins
39
 Proteins
Proteins are the most abundant biomolecules
of the living system. Chief sources of proteins
are milk, cheese, pulses, peanuts, fish, meat,
etc. They form the fundamental basis of
structure and functions of life. They are also
required for growth and maintenance of body.
All proteins are polymers of α-amino acids.

40
 Amino acids
Amino acids contain amino (–NH 2) and
carboxyl (–COOH) functional groups.

41
 Classification
Neutral—Equal no. of amino and carboxyl group make
amino acid neutral

Basic--More no. of amino than carboxyl group make

amino acid basic

Acidic-- More no. of carboxyl than amino group make

amino acid acidic

42
Classification of Amino Acids
The amino acids, which can be synthesised in
the body, are known as non essential amino
acids. Eg: Glycine, Alanine
Amino acids which cannot be synthesised in
the body and must be obtained through diet,
are known as essential amino acids Eg: Valine,
Leucine

43
 Physical properties
Amino acids are usually colourless, crystalline solids.
These are water-soluble, high melting solids and
behave like salts. They form zwitter ion in which
amino acids show amphoteric behaviour

44
 Structure of Proteins
Proteins are the polymers of α-amino acids and
they are connected to each other by peptide bond
or peptide linkage. Chemically, peptide linkage
is an amide formed between –COOH group and
–NH2 group.
If two amino acids combine, it is called
dipeptide. Tripeptide, tetrapeptide, pentapeptide
etc are used for 3,4,5 respectively.

45
46
Classification of protein
Based on molecular structure, they are
classified as
Fibrous proteins and
Globular proteins

47
 Fibrous proteins
When the polypeptide chains run parallel and
are held together by hydrogen and disulphide
bonds, then fibre– like structure is formed.
Such proteins are generally insoluble in water.
Some common examples are keratin (present in
hair, wool, silk) and myosin (present in
muscles), etc.

48
 Globular proteins
This structure results when the chains of
polypeptides coil around to give a spherical
shape. These are usually soluble in water.
Insulin and albumins are the common
examples of globular proteins.

49
Structure and shape of proteins
Their structure consists of four different
levels.
Primary
 secondary
tertiary and
quaternary

50
Primary structure of proteins
Proteins may have one or more polypeptide
chains. This sequence of amino acids is said to
be the primary structure of that protein.

51
Secondary structure of proteins
The secondary structure of protein refers to
the shape in which a long polypeptide chain
can exist. They are found to exist in two
different types of structures viz. α-helix and β-
pleated sheet structure.
In α-Helix polypeptide chain forms all
possible hydrogen bonds by twisting into a
right handed screw (helix)
52
53
In β-structure all peptide chains are stretched
out to nearly maximum extension and then laid
side by side which are held together by
intermolecular hydrogen bonds in a sheet like
structure.

54
55
 Tertiary structure of proteins
The tertiary structure of proteins represents
overall folding of the polypeptide chains i.e.,
further folding of the secondary structure. It
gives rise to two major molecular shapes viz.
fibrous and globular.

56
Quaternary structure of proteins
Some of the proteins are composed of two or
more polypeptide chains referred to as sub-
units. The spatial arrangement of these
subunits with respect to each other is known as
quaternary structure.

57
58
Denaturation of Proteins
When protein is subjected to physical change
like change in temperature or chemical change
like change in pH, the hydrogen bonds are
disturbed. Due to this, globules unfold and
helix get uncoiled and protein loses its
biological activity. This is called denaturation
of protein. During denaturation 2° and 3°
structures are destroyed but 1º structure
remains intact.
59
 Enzymes
Enzymes are biocatalysts that, within the mild
conditions of temperature and pH, of the cells, carry
out chemical reactions at amazing high rate.
 They are characterized by a remarkable efficiency
and specificity.
Almost all enzymes are globular proteins.
Enzymes are named by adding the suffix -ase to the
name of the substrate that they modify

60
Mechanism of enzyme action

61
Vitamins
62
 Vitamins
Certain organic compounds are required in
small amounts in our diet but their deficiency
causes specific diseases. These compounds are
called vitamins.
Vitamins are designated by alphabets A, B, C,
D, E & K. Some of them are further named as
sub-groups e.g. B1, B2, B6, B12, etc. Excess of
vitamins is also harmful.
63
 Classification of Vitamins
Fat soluble vitamins
Vitamins which are soluble in fat and oils but
insoluble in water are kept in this group. These
are vitamins A, D, E and K. They are stored in
liver and adipose (fat storing) tissues.
Water soluble vitamins
B group vitamins and vitamin C are soluble in
water so they are grouped together.
64
65
Nucleic Acids

66
 Nucleic Acids
The particles in nucleus of the cell,
responsible for heredity, are called
chromosomes which are made up of proteins
and another type of biomolecules called
nucleic acids.
These are mainly of two types,
Deoxyribonucleic acid (DNA) and
Ribonucleic acid (RNA).
67
 Chemical Composition of
Nucleic Acids
Complete hydrolysis of DNA (or RNA) yields
a pentose sugar, phosphoric acid and nitrogen
containing heterocyclic compounds (called
bases).
In DNA molecules, the sugar is β-D-2-
deoxyribose whereas in RNA molecule, it is β-
D-ribose.

68
Pentose sugars

69
 Nitrogen Bases
DNA contains four bases viz. adenine (A),
guanine (G), cytosine (C) and thymine (T).
RNA also contains four bases, the first three
bases are same as in DNA but the fourth one is
uracil (U).

70
 Nitrogen Bases
O
NH2
H CH3
N N
N

N O N
N
H H
adenine (A) thymine (T)
O NH 2 O
H N CH3 H CH 3
N N N

NH 2 N N O N O N
H H H
guanine (G) cytosine (C) uracil (U)

71
 Structure of Nucleic Acids
A unit formed by the attachment of a base to
1′ position of sugar is known as nucleoside.
When nucleoside is linked to phosphoric acid
at 5′-position of sugar moiety, we get a
nucleotide.

72
 Nucleotide
NH2

O O N
-
O P O CH2
-
O
O

OH

deoxyctyidine monophosphate (dCMP)

73
 DNA Nucleotide
Phosphate
Group

O 5
O=P-O CH2
O
O
N
Nitrogenous base
C4 C
1
(A, G, C, or T)
Sugar
(deoxyribose)
C3 C2 74
 Joining of nucleotides
Nucleotides are joined together by
phosphodiester linkage between 5′ and 3′
carbon atoms of the pentose sugar. The
formation of a typical dinucleotide

75
Formation of a dinucleotide

76
 Structure of DNA
The sequence of nucleotides in the chain of a
nucleic acid is called its primary structure.
Nucleic acids have a secondary structure also.
James Watson and Francis Crick gave a double
strand helix structure for DNA. Two nucleic
acid chains are wound about each other and
held together by hydrogen bonds between pairs
of bases.
77
Double Helix of DNA

78
 The two strands are complementary to each
other because the hydrogen bonds are formed
between specific pairs of bases. Adenine forms
hydrogen bonds with thymine whereas
cytosine forms hydrogen bonds with guanine.

79
 Base pairing by unique hydrogen bonds
 C - G and A - T pairs

80
Secondary Structure of RNA
In secondary structure of RNA, helices are
present which are only single stranded.
Sometimes they fold back on themselves to
form a double helix structure. RNA molecules
are of three types and they perform different
functions. They are named as messenger RNA
(m-RNA), ribosomal RNA (r-RNA) and
transfer RNA (t-RNA).

81
Biological Functions of Nucleic Acids
DNA is the chemical basis of heredity. DNA
is exclusively responsible for maintaining the
identity of different species of organisms over
millions of years. A DNA molecule is capable
of self duplication during cell division and
identical DNA strands are transferred to
daughter cells.

82
 Another important function of nucleic acids is
the protein synthesis in the cell. Actually, the
proteins are synthesised by various RNA
molecules in the cell but the message for the
synthesis of a particular protein is present in
DNA.

83
THE END

84