Live Sahab20

Biomolecules

By Singh Sahab
Introduction
Living systems are made up of various complex biomolecules like

• Carbohydrates
• Proteins
• Nucleic acids
• Lipids, etc.
Carbohydrates
✓ Hydrates of carbon

✓ Optically active polyhydroxy aldehydes or ketones or the compounds

which produce such units on hydrolysis.

✓ Contain specific functional groups.

Examples - cane sugar, glucose, starch, etc.

Most of Carbohydrates have a general formula- Cx(H2O)y .

Example –

Glucose (C6H12O6) → C6(H2O)6.

Maltose (C12H22O11) → C12(H2O)11

But….
✓ Acetic acid (CH3COOH) → C2(H2O)2
Acetic Acid fits in formula but is not a carbohydrate.
It is an acid.

✓ Rhamnose (C6H12O5) does not fit into formula

But it is a carbohydrate
Sugars - carbohydrates sweet in taste

• Sugar used in our homes → sucrose

• Sugar in milk → lactose

Carbohydrates are also called saccharides

(Greek: sakcharon means sugar).

Classification
Based on their behaviour on hydrolysis-

(i) Monosaccharides

A carbohydrate that cannot be hydrolysed further to give simpler unit of

polyhydroxy aldehyde or ketone.

Examples - glucose, fructose, ribose, etc.

(ii) Oligosaccharides

Carbohydrates that yield 2 - 10 monosaccharide units on hydrolysis.

Depending upon the number of monosaccharides produced on hydrolysis.

They are further classified as

• Disaccharides (2)

• Trisaccharides (3)

• Tetrasaccharides (4)

• And so on
Most Common Oligosaccharides- Disaccharides.

✓ The two monosaccharide units obtained on hydrolysis of a

disaccharide may be same or different.

For example

1. Sucrose on hydrolysis → one molecule of glucose & fructose

2. Maltose → two molecules of glucose.

(iii) Polysaccharides:

Carbohydrates which yield a large number of monosaccharide units on

hydrolysis.

Examples - starch, cellulose, glycogen, gums, etc.

✓ Polysaccharides are not sweet in taste.

✓ Also called non-sugars.

Reducing or non-reducing sugars

Reducing sugars - carbohydrates which reduce Fehling’s solution and

Tollens’ reagent.

Example- All monosaccharides (aldose or ketose).

In disaccharides-

Non-reducing sugars → if the reducing groups of monosaccharides

(aldehydic or ketonic) are bonded
e.g. - sucrose.

Reducing sugars → sugars in which these functional groups are free,

e.g. - maltose and lactose.
Monosaccharides

Aldose- If monosaccharide contains aldehyde group

Ketose- If monosaccharide contains keto group

Classification-
Based on number of carbon atoms & the functional group
Glucose
✓ Glucose is an aldohexose

✓ Also known as dextrose.

✓ Monomer of many of the larger carbohydrates like starch, cellulose.

✓ Present in sweet fruits and honey

Preparation of Glucose

1. From sucrose (Cane sugar):

2. From starch:
Structure of Glucose

Assigning Glucose a particular structure-

1. Observation- Its molecular formula was found to be C6H12O6.

2. Observation - On prolonged heating with HI, it forms n-hexane.

Result- all the six C-atoms are linked in a straight chain.

3. Observation- Glucose reacts with hydroxylamine to form an oxime
and adds a molecule of hydrogen cyanide to give cyanohydrin.

Result- presence of a carbonyl group (>C = 0) in glucose.

4. Observation- Glucose gets oxidised to six carbon carboxylic acid
(gluconic acid) on reaction with a mild oxidising agent (bromine water).

Result- carbonyl group is present as an aldehydic group.

5. Observation- Acetylation of glucose with acetic anhydride gives glucose
pentaacetate.

Result- presence of five –OH groups.

Since it exists as a stable compound → five –OH groups should be attached

to different C-atoms.
6. Observation- On oxidation with HNO3, glucose as well as gluconic
acid both yield a saccharic acid (dicarboxylic acid).

Result- presence of a primary alcoholic (–OH) group in glucose.

Spatial arrangement

Glucose Gluconic acid Saccharic acid

Glucose is correctly named as D(+)-glucose.

‘D’ represents the configuration

‘(+)’ represents dextrorotatory nature of the molecule.

Note-
‘D’ and ‘L’ have no relation with the optical activity of the compound.
Glyceraldehyde exists in two enantiomeric forms-
D and L are assigned with relation to glyceraldehyde-

Compounds which can be chemically correlated to (+) isomer of

glyceraldehyde → have D-configuration

And those which can be correlated to (–) isomer of glyceraldehyde

→ have L—configuration
 Assigning the configuration (D/L)

➢ Lowest asymmetric carbon atom is compared.

➢ Structure is written in a way that most oxidised carbon is at the top.

Cyclic Structure of Glucose

Straight structure of glucose cannot explain following reactions/facts-

1. Despite having the aldehyde group glucose does not give

• 2,4-DNP test

• Schiff’s test

Also, It does not form the hydrogensulphite addition product with NaHSO3.
2. The pentaacetate of glucose does not react with hydroxylamine

Indication- absence of free —CHO group.

3. Glucose exists in two different crystalline forms
1. 

2. β

α-form (m.p. 419 K) - obtained by crystallisation from concentrated

solution of glucose at 303 K

β-form (m.p. 423 K) - obtained by crystallisation from hot and saturated

aqueous solution at 371 K.
Now- It was proposed that-

➢ one of the —OH groups may add to the —CHO group and form a cyclic
hemiacetal structure.

➢ Glucose forms a six-membered ring in which —OH at C-5 is involved in

ring formation.
Proposed structure explains

• absence of —CHO group

• existence of glucose in two forms

Important-

The two cyclic hemiacetal forms of glucose differ only in the

configuration of the hydroxyl group at C1

This carbon is called anomeric carbon (the aldehyde carbon before

cyclisation).

Isomers (α-form and β-form) are called anomers.

Six membered cyclic structure
Called Pyranose structure (α– or β–)
Fructose
• Molecular formula - C6H12O6

• A ketohexose.

• obtained along with glucose by the hydrolysis of disaccharide, sucrose.

Structure of Fructose

On the basis of its reactions it was found –

• It contain a ketonic functional group at carbon number 2

• six carbons in straight chain

It is D-series and laevorotatory compound.

Written as D-(–)-fructose.
Fructose open chain-
Important-

Fructose also exists in two cyclic forms obtained by the addition of —OH
at C5 to the carbonyl group.

Furanose structure with analogy to the furan.

The cyclic structures of two anomers of fructose
 Disaccharides
Disaccharides on hydrolysis yield two monosaccharides either the same or
different.

Glycosidic linkage

The two monosaccharides are joint by an oxide linkage formed by the loss
of a H2O molecule.
(i) Sucrose:

Hydrolysis-
Glycosidic linkage between C1 of α-glucose and C2 of β-fructose.

Note- Sucrose is a non reducing sugar

Sucrose is dextrorotatory

On hydrolysis gives
1. dextrorotatory glucose
2. laevorotatory fructose.

laevorotation of fructose (–92.4°) > dextrorotation of glucose (+ 52.5°)

Hence, the mixture is laevorotatory.

So hydrolysis of sucrose changes it from dextro (+) to laevo (–)

and this product is named as invert sugar.
(ii) Maltose
Two α-D-glucose units with C1 - C4 linkage.

The free aldehyde group at C1 of second glucose, so it is a reducing sugar.

(iii) Lactose
• Found in milk.
• Composed of β-D-galactose & β-D-glucose.

The linkage is between C1 of galactose & C4 of glucose.

So Lactose is a reducing sugar
Polysaccharides
✓ These contain a large number of monosaccharide units joined
together by glycosidic linkages.

✓ Most common carbohydrates.

✓ Mainly act as the food storage or structural materials.

Starch

Found in cereals, roots, and some vegetables.

Polymer of α-glucose.

Consists of two components—

1. Amylose
2. Amylopectin.
Amylose

Long unbranched chain with 200-1000 α-D-(+)-glucose units held by C1–

C4 glycosidic linkage.

• water soluble component

• constitutes about 15-20% of starch.

Amylopectin
Branched chain polymer of α-D-glucose units
Chain is formed by C1–C4 glycosidic linkage
Branching occurs by C1–C6 glycosidic linkage.

• insoluble in water
• constitutes about
80- 85% of starch
(ii) Cellulose

Constituent of cell wall of plant cells.

• 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.
(iii) Glycogen
Stored in animal body as glycogen.

Also known as animal starch because

1. its structure is similar to amylopectin
2. more highly branched.

When the body needs glucose, enzymes break the glycogen down to
glucose.
Importance of Carbohydrates

• Essential for both plants and animals.

• Form a major portion of our food.

• Used as storage molecules as starch in plants and glycogen in animals.

• Cell wall of bacteria and plants is made up of cellulose.

• They provide raw materials for many important industries like textiles,
paper, lacquers and breweries.
Proteins
• fundamental basis of structure and functions of life.

• Required for growth and maintenance of body.

All proteins are polymers of α-amino acids.

Chief sources of proteins - milk, cheese, pulses, peanuts, fish, meat, etc.
Amino Acids
Amino acids contain-

1. Amino (–NH2)

2. Carboxyl (–COOH)
Depending upon the relative position of amino group with
respect to carboxyl group, the amino acids are classified as-
1. α
2. β
3. γ
4. δ and so on.

Note-

• Only α-amino acids are obtained on hydrolysis of

proteins.

• They may contain other functional groups also.

❖ Amino acids are generally represented by a three letter symbol.

* essential amino acid

Classification of Amino Acids

Depending upon the relative number of amino and carboxyl groups amino
acids are classified as –
1. Acidic - more carboxyl groups than amino groups makes it.
2. Basic - more number of amino than carboxyl groups
3. Neutral - Equal number of amino and carboxyl groups
Nonessential amino acids- The amino acids, which can be synthesised
in the body.

Essential amino acids- Those which cannot be synthesised in the body

and must be obtained through diet
Properties

Amino acids are usually

• Colourless
• crystalline solids
• water-soluble

These are high melting solids.

Zwitter ion

Amino acids behaves like salts rather than simple amines or carboxylic
acids.
Reason- due to the presence of both acidic (carboxyl group) and basic
(amino group) groups in the same molecule.
Optical Activity-

Except glycine, all other naturally occurring α-amino acids are optically
active

Reason- since the α-carbon atom is asymmetric.

• These exist both in ‘D’ and ‘L’ forms.

• Most naturally occurring amino acids have L-configuration.

Representation-

L-Aminoacids - represented by writing the –NH2 group on left side.

Structure of Proteins
• Proteins are the polymers of α-amino acids

• They are connected to each other by peptide bond or peptide linkage.

• Peptide linkage is an amide formed between –COOH group and –NH2 group.
Formation of peptide linkage-

The product of the reaction is called a dipeptide

Reason- it is made up of two amino acids.
• If third amino acid combines to a dipeptide, the product is called a
tripeptide.

• Similarly for tetrapeptide, pentapeptide or hexapeptide,...

• If number of such amino acids > 10 → polypeptides

Proteins

A polypeptide with more than 100 amino acid residues, having molecular
mass higher than 10,000u.
Classification of Proteins:

Two types on the basis of their molecular shape

(a) Fibrous proteins

Fibre– like structure is formed when the polypeptide chains run parallel and
are held together by hydrogen and disulphide bonds.

• generally insoluble in water.

Examples –
• keratin (present in hair, wool, silk)
• myosin (present in muscles), etc.
(b) Globular proteins:
Formed when the chains of polypeptides coil around to give a spherical shape.
• Usually soluble in water.
Example- Insulin and albumins

Four different levels of proteins-

• Primary
• Secondary
• Tertiary
• Quaternary.
(i) Primary structure of proteins:
• Proteins may have one or more polypeptide chains.

• Each polypeptide in a protein has amino acids linked with each other in
a specific sequence.

• This sequence of amino acids is said to be the primary structure of that

protein.

• Any change in this primary structure i.e., the sequence of amino acids
creates a different protein.
(ii) Secondary structure of proteins:
Long polypeptide chain can exist.

They exist in two different types –

1. α-helix
2. β-pleated sheet structure

These structures arise due to the regular folding of the backbone of the
polypeptide chain due to hydrogen bonding between -CO-and –NH–
groups of the peptide bond.
α-Helix
Polypeptide chain forms all
possible H-Bonds by twisting
into a right handed screw
(helix) with the –NH group of
each amino acid residue
hydrogen bonded to the
–CO- of an adjacent turn of
the helix
β-structure
All peptide chains are stretched out to
nearly maximum extension and then
laid side by side which are held
together by intermolecular H - bonds.

The structure resembles the pleated

folds of drapery and thus called β-
pleated sheet.
(iii) Tertiary structure of proteins:

It is further folding of the secondary structure.

It gives rise to two major molecular shapes-

1. Fibrous
2. Globular.
The main forces which stabilise the 2° and 3° structures of proteins are

➢ H-bonds

➢ disulphide linkages

➢ van der Waals

➢ and electrostatic forces of attraction.

(iv) 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.
Denaturation of Proteins
Native protein- Protein found in a biological system with a unique three-
dimensional structure and biological activity.

When a native protein is subjected to physical change like

➢ change in temperature or
➢ chemical change or
➢ change in pH

As a result- 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.

Examples-
• The coagulation of egg white on boiling.
• Curdling of milk
Enzymes
Digestion of food, absorption of appropriate molecules and production of energy
takes place by various chemical reactions.

This occurs with the help of certain biocatalysts called enzymes.

Almost all the enzymes are globular proteins.

Enzymes are very specific for a particular reaction and for a particular substrate.
Naming-
They are generally named after the compound or class of compounds
upon which they work.

For example, the enzyme that catalyses hydrolysis of maltose into

glucose is named as maltase.
Sometimes enzymes are also named after the reaction, where they are
used.

For example, the enzymes which catalyse the oxidation of one substrate
with simultaneous reduction of another substrate are named as
oxidoreductase enzymes.

The ending of the name of an enzyme is -ase.

Mechanism of Enzyme Action

Enzymes reduce the magnitude of activation energy.

For example,
activation energy for acid hydrolysis of sucrose is 6.22 kJ mol–1, while the
activation energy is only 2.15 kJ mol–1 when hydrolysed by the enzyme,
sucrase.
Vitamins
Certain organic compounds are required in small amounts in our diet but their
deficiency causes specific diseases.
These compounds are called vitamins.

Most of the vitamins cannot be synthesised in our body but plants can synthesise
almost all of them.
Vitamins- organic compounds required in the diet in small amounts to
perform specific biological functions for normal maintenance of optimum
growth and health of the organism.

Vitamins are designated by alphabets A, B, C, D, etc.

Some of them are further named as sub-groups e.g. B1, B2, B6, B12, etc.
Classification of Vitamins

Based on solubility in water or fat.

(i) Fat soluble vitamins: soluble in fat / oils but insoluble in water.

Example- vitamins A, D, E and K.

(ii) Water soluble vitamins: B group vitamins and vitamin C are soluble in

water.
Note-
Water soluble vitamins must be supplied regularly in diet because they
are readily excreted in urine and cannot be stored (except vitamin B12) in
our body.
Nucleic Acids
The particles in nucleus of the cell, responsible for heredity, are called
chromosomes

These are made up of proteins and another type of biomolecules called

nucleic acids.

These are mainly of two types-

• deoxyribonucleic acid (DNA)
• ribonucleic acid (RNA)

Nucleic acids are long chain polymers of nucleotides, so they are also called
polynucleotides.
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 moiety is β-D-2-deoxyribose

In RNA molecule -> it is β-D-ribose.
DNA contains four bases
RNA contains four bases
Structure of Nucleic Acids

Nucleoside- A unit formed by the attachment of a base to 1′ position of

sugar.

In nucleosides, the sugar carbons are numbered as 1′, 2′, 3′, etc. in order to
distinguish these from the bases.
Nucleotide- When nucleoside is linked to phosphoric acid at 5′-
position of sugar moiety

Nucleotides are joined together by phosphodiester linkage between 5′ and

3′ carbon atoms of the pentose sugar.
The formation of a dinucleotide
A simplified version of nucleic acid chain
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.

The two strands are complementary to each other

because the hydrogen bonds are formed between
specific pairs of bases.

• Adenine forms H bonds with thymine

• Cytosine forms H bonds with guanine.
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)
• transfer RNA (t-RNA).