CHAPTER 14

BIOMOLECULES

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CARBOHYDRATES

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Carbohydrates (glycans) have the following
basic composition: I
(CH2O)n or H - C - OH
I
 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.
 Disaccharides - 2 monosaccharides covalently linked.
 Oligosaccharides - a few monosaccharides covalently
linked.
 Polysaccharides - polymers consisting of chains of
monosaccharide or disaccharide units. 3
 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
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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
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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.

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Glucose

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 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
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 Structure of Glucose
Glucose is an aldohexose

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

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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 NaHSO3.
The pentaacetate of glucose does not react with
hydroxylamine indicating the absence of free —CHO
group.

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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
below.

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 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
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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 13
 Fructose
Fructose is an important ketohexose. It is
obtained along with glucose by the hydrolysis
of disaccharide, sucrose.

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 Structure of Fructose
Open chain structure
CH2OH

C O

HO C H

H C OH

H C OH

CH2OH

D-fructose
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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

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 Disaccharides
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.

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 Sucrose
Sucrose contains 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.

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 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.

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 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).

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

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 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.

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23
 Polysaccharides
Starch
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.

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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
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 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 2 OH 6 CH 2 CH 2 OH 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 2
3
H OH H OH H OH H OH H OH

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 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.

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 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.

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 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.

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Proteins
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 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.

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 Amino acids
Amino acids contain amino (–NH2) and
carboxyl (–COOH) functional groups.

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Classification of Amino Acids
The amino acids, which can be synthesised in
the body, are known as nonessential amino
acids.
Amino acids which cannot be synthesised in
the body and must be obtained through diet,
are known as essential amino acids

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 Physical properties
Amino acids are usually colourless, crystalline
solids. These are water-soluble, high melting
solids and behave like salts. They form zwitter
ion

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35
 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.

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

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 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.

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 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.

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

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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.

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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)
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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.

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 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.

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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.

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48
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.

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Enzymes

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Vitamins
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 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.
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 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.
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Nucleic Acids

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 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).
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 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.

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Pentose sugars

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 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).

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 Nitrogen Bases
O
NH2
H CH 3
N N
N

N O N
N
H H
adenine (A) thymine (T)
O NH2 O
H N CH3 H CH 3
N N N

NH2 N N O N O N
H H H
guanine (G) cytosine (C) uracil (U)

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 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.

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 Nucleotide
NH2

O O N
-
O P O CH2
-
O
O

OH

deoxyctyidine monophosphate (dCMP)

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 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 62
 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

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Formation of a dinucleotide

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 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.
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Double Helix of DNA

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 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.

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

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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).

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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.

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 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.

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THE END

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