Biomolecules

Introduction
 These substances formed the basis of life and are
responsible for growth and maintenance of all
living organisms.

 These substances are biomolecules

Biomolecules

 Biomolecules build up the living system.

 Biomolecules are carbohydrates, proteins,

nucleic acids, vitamins etc.
carbohydrates
 Theseare hydrates of carbon, I’e.,those
have C,H and O. General formula is
Cx(H2O)y.
 Thestructures that are known to satisfy this
formula are:
 For example:-
 Glucose/fructose – C6H12O6 or C6(H2O)6
 Sucrose – C12H22O11 or C12(H2O)11
 As,
there are many molecules that, satisfy
similar criteria but are not carbohydrates.
 For example:- Acetic acid
 CH3COOH  C2H4O2  C2(H2O)2
 But this is not a carbohydrate.
 There are a lot of compounds that do not
satisfy the formula but are carbohydrates.
 For example :- Rhamnose
 C6H12O5  it does not satisfy the formula,
but it is a carbohydrates.
Carbohydrates

 Carbohydrates are optically active poly

hydroxyl aldehyde of ketones or substances
which produce these on hydrolysis and have
at least one chiral carbon atom.
 Forexample :- glucose, fructose, lactose,
sucrose, maltose etc.
 Classification of Carbohydrates
 (1) On the basis of hydrolysis product
 Monosaccharides
 Oligosaccharides
 Polysaccharides
 (2) On the basis of reducing properties
 Reducing sugar
 Non – reducing sugar
 (3) On the basis of taste
 Sugars
 Non - sugars
Monosaccharides
Monosaccharides
 It is the simplest carbohydrate,
which cannot be hydrolysed further
to give simpler molecules of poly
hydroxyl aldehyde and ketone.
 The general formula is CnH2nOn.
 For example :- glucose, fructose,
ribose etc.
Classification of Monosaccharides
 On the basis of functional group present
 (1) Aldose  having –CHO group
 (2) ketose  having =C=O group
 Ifa monosaccharides have an aldehyde group. It is known
as an aldose and if have ketone group, it is known as
ketose.
 No. of General Aldehyde Ketones
carbon atom term
3 Triose Aldotriose Ketotriose

4 Tetrose aldotetrose Ketotetrose

5 Pentose Aldopentose Ketopentose

6 Hexose Aldohexose Ketohexose

7 Heptose Aldoheptose Ketoheptose

Glucose

 Itis present in honey and

sweet fruits etc.
 It is an aldohexose.
 Itis also known as dextrose
as it is dextrorotatory.
 Glucose is also called blood sugar as it
circulates in the blood at a concentration
of 65 – 100 mg/ml of blood.
 It is synthesised by chlorophyll in plants by
using water and carbon dioxide from the
air and sunlight as an energy source.
 Glucose made in the leaves is then
converted into starch for storage.
 Preparation of Glucose
 It is prepared from sucrose and starch
 From Sucrose
 On boiling sucrose with dilute HCl or H2SO4
in alcoholic solution, equal amounts of
glucose and fructose are obtained.
 From Starch

 When starch is boiled with dilute H2SO4 at

393 K temperature and 2 – 3 atm pressure,
glucose is obtained.
Structure of Glucose
 The open
chain
structure of
glucose is
given on the
basis of
various
evidences.
Evidences in support of open structure
of glucose
 (1)Glucose on reduction with HI and red P
at 373 K, gives a mixture of n-Hexane and
2-Iodohexane suggesting that all the 6
carbons are linked in a straight chain.
 (2)glucose forms an oxime with
hydroxylamine (NH2OH).
 (3)On adding a molecule of hydrogen
cyanide, glucose forms cyanohydrin.
 (4)On oxidation with mild oxidising agent
bromine water, glucose gives gluconic acid.

 It confirms the presence of aldehyde group.

 (5)Glucose on acetylation with acetic
anhydride forms a penta acetate.

 It confirms the presence of 5 -OH group.

 (6)On oxidation with nitric acid, both glucose
and gluconic acid form the same product.

 Itconfirms the presence of primary alcoholic

(-OH) group in glucose.
 Fischerafter studying many properties of
glucose gave the exact spatial arrangement of
–OH groups.
 D  represent the
configuration of the –OH
group at the last carbon.

 (+)  stands for optical

rotation, I’e.,
dextrorotatory.

 ‘D’ and ‘L’ notations are

not related to the optical
activity of the compounds.
Enantiomers

 Moleculesthat are non-superimposable

mirror images are called enantiomers.
 Notations d, l or (+), (-) are used to show optical
rotations.

 Dextrorotatory(‘+’ or ‘d’):- enantiomer which rotates

the plane of polarised light towards right.
 Laevorotatory (‘-’ or ‘l’):- enantiomer which rotates the
plane of polarised light towards left.
D and L -Configuration

 Compound chemically  Compound chemically

correlated to (+) or ‘d’ correlated to (-) or ‘l’
isomer of isomer of
glyceraldehyde is glyceraldehyde is
assigned D- assigned L-
configuration. configuration.
 The–OH group on the lowest asymmetric
carbon is on the right side.
Reactions which do not support
proposed structure of glucose
 Theopen chain structure of glucose explains
most of its reactions, yet it fails to explain
the following facts.
 Despitehaving the aldehyde group, glucose
does not give 2,4-DNP test.
 Despitehaving the aldehyde group, glucose
does not give Schiff’s test.
 Glucose, on reaction with sodium
bisulphite, does not form the addition
product.
 Pentaacetate of glucose does not react with
hydroxylamine.

 These
reactions indicate the absence of free –
CHO group in glucose.
Cyclic structure of glucose

 Fischer Projection
 The α-glucose and β-glucose, differ only in the
orientation of the hydroxyl group at C-1 atom.
 Such pairs of the optical isomers that differ
only in the orientation of H and OH group at C-
1 atom are called anomers.
 The C-1 atom is called anomeric carbon atom
(or glycosidic carbon).
 Itwas found that the –OH group at C-5 in
glucose combines with the –CHO group and
forms cyclic hemiacetal structure.
Haworth Projection
 Haworth proposed a 6-membered cyclic
structure for glucose, based on the structure of
a hetrocyclic compound pyran.

 Sucha structure is known as the pyranose

structure.
 Haworth projection of α-glucose and β-
glucose are as follows;
Fructose
 It is ketohexose
 It have keto group
 Natural monosaccharide,
found in fruits and honey.
 Itmelts with slight
decomposition at 102
degree celsius.
 It is laevorotatory; as it
rotates plane polarised
light to the left.
Cyclic structure of fructose
 Haworth proposed a 5-membered cyclic
structure for fructose, based on the
structure of a hetrocyclic compound furan.
 Sucha structure is known as the furanose
structure.
Protein
 Proteinsare found in almost all the living cell of
the plants and animals.
 Proteins constitute about 20% of the living cell.
 Theyare essential for the growth and
maintenance of life.
 Proteins
are highly complex nitrogenous organic
compounds of high molecular mass.
 They are polyamides.
 They are condensation polymer of α-amino
acids.
 Successive hydrolysis of proteins;

 Amino acids:- they are basic building units of

proteins.
 The number of amino acids in proteins may
vary.
Amino acids
 Thecompounds which have carboxylic acid
group and amino group are called amino
acids.
 They are obtained on hydrolysis of protein.
 Theyare differ from one another in the
nature of side chain.
 Nearly,
all naturally occurring amino acids
are α-amino acids.
 Those amino acids in which NH2 group and
COOH group attached to the same carbon
are called α-amino acids.
Classification of α-Amino Acids
 Onthe basis of the relative number of
amino and carboxylic groups.
Acidic Amino Acids
 When the number of amino group is less
than the number of carboxylic acid group in
the molecule of amino acid, it is called
acidic amino acid.
Basic Amino Acids
 When the number of amino group is more
than the number of carboxylic acid group in
the molecule of amino acid, it is called
basic amino acid.
Neutral Amino acids
 When the number of amino and carboxylic
group is equal in the molecule of amino
acid, it is called neutral amino acid.
Essential and Non-essential Amino
Acids
 Outof the 20 α-amino acids required for
protein synthesis, only 10 can be synthesised
in human body.

 Onthis basis, α-amino acids are classified as

essential and non-essential amino acids.
Essential Amino acids
 Thoseamino acids which are not
synthesised by our body are called essential
amino acids.
 Their
deficiency can be cause diseases like
Kwashiorkor.
Non-essential Amino Acids
 Those amino acids which are synthesised by
our body are called non-essential amino
acids.
Properties of amino acids
 Amino acids are usually colourless, crystalline
solid.
 These are water soluble with high melting point.
 They behave like salt due to presence of basic
amino group and acidic due to carboxylic group.
 In aqueous solution, the carboxylic group can
lose a proton and amino group can accept a
proton to give a dipolar ion which is known as
‘Zwitter ion’.
Zwitter ion
 Amino acids show amphoteric nature. They
react with both acids and bases.
 Inacidic solution, Amino acids group
accepts a proton.
 Inbasic solution, carboxylic group loses a
proton.
Classification of proteins
 Onthe basis of molecular shape, proteins
are classified into two categories.

Proteins

Fibrous Globular
proteins proteins
 Fibrous proteins
 In fibrous proteins, polypeptide chains are
held together by hydrogen bonds and
disulphide bonds and form fibre-like
structure.
 Generally, insoluble in water.
 For example:- keratin in skin, hair, feather
etc.
Globular proteins
 Inglobular proteins, the chains of
polypeptides are folded together into
compact units.
 They are soluble in water.
 They act as enzymes to catalyse the
biological reactions.
 Some of them regulate metabolic reactions.
 Sone act as antibodies.
 For example:- albumin and insulin.
Structure of proteins (Peptide Bond)
 Peptide link is repeated many times to produce a
polypeptide.
 A polypeptide with more tan 100 amino acid is
called protein.
 Proteinsare condensation polymers, also
categorised as polyamides due to the
presence of –CONH group.
Structure of Proteins
Primary structure of proteins

 Proteinshave one or more polypeptide chain.

Each polypeptide in a protein has amino acids
linked with each other in a specific sequence
of amino acids in a protein is called primary
structure of proteins.
Secondary structure of Proteins
 The arrangement of peptide chain into 3-D
structures is called secondary structure of
proteins.
 This arrangement is due to the folding of chain.
 The folding is due to hydrogen bond and peptide
bond between carbonyl and –NH- groups of
different peptide bonds.
 It gives the shape of the protein molecule.
 The folding gives two types of structures;
 (1) α-helix (2) β-pleated sheets
α-Helix
 Itis formed when
the chain of α-amino
acids coils as a right
hand screw.
 Itis due to the
formation of
hydrogen bonds
between the amide
groups of the same
peptide chain.
 β-Pleated sheet
 It is formed when the chain of the α-amino acids are
arranged side by side. The chains are held together
by a very large number of H-bonds.
β -pleated sheet is not a very stable
structure because of van der waal repulsion
between the substituents on the –carbon
atom of one side chain and the
corresponding substituents on the
neighbouring chain.
β -pleated sheets are arranged in two ways;
(1) parallel β–sheet
(2) Anti-parallel β-sheet
 Parallelβ-
sheet:-Amino
acid chains
run in the
same
direction.
 Antiparallel
β-sheet:-
Amino acid
chains run in
opposite
direction.
 Tertiary structure of proteins
 Itarises due to the further
folding, coiling and bending
of the secondary structure.
 Itgive the overall shape of
proteins.
 The attractive forces
between the amino acid side
chain make the proteins
result in a compact and
complex structure.
Quaternary structure of proteins
 Quaternary structure
determines the number
of sub-units and their
arrangement in a protein
molecule.
 Sub-units
are joined to
form proteins with the
molecular mass greater
than 50000 amu.
Denaturation of proteins
 Itis the change in the physical and
biological properties without affecting its
chemical composition.
 Causes;
 Change in pH
 Change in temperature
 Presence of some salts or chemicals
 Duringdenaturation, the protein molecule
uncoils from an ordered and specific
conformation into a more random
conformation.
Nucleic acid
 Nucleic acid are biomolecules which are found in the
nuclei of all living organism or cells in the form of
nucleoprotein.
 They are biopolymers in which the repeating structural
unit or monomeric unit is a nucleotide, so that nucleic
acid are also called polynucleotides.
 Each nucleotides have three components.
 (1) pentose sugar  ribose, deoxyribose
 (2) nitrogenous base  these are of two types,
 (a) purines  adenine, guanine
 (b) pyrimidines  cytosine, thymine, uracil
 (3) phosphoric acid
 Nucleosides
A base joined to a
sugar molecule is
called nucleosides.
 Depending upon the
sugar present, there
are two types of
nucleotides;
ribonucleoside and
deoxyribonucleoside
Nucleotides
A nucleotide have all the three
components. I’e., pentose sugar,
nitrogenous base and phosphoric acid.
The two nucleotides are connected by a
phosphodiester linkage
Glycosidic linkage
 Thebond formed between C1 atom of sugar
and nitrogen atom of the nitrogenous base.
Nucleotide chain in a nucleic acid
DNA (deoxyribonucleic acid)
 Itis genetic material responsible for the
hereditary character of the cell
 Present in the nucleus of the cell
 Composition;
 (1) A pentose sugar  deoxyribose
 (2) Four nitrogenous bases
 (a) Purine; adenine, guanine
 (b) Pyrimidine; thymine, cytosine
 (3) phosphate group
Structure of DNA
 The double-helix structure of
DNA was established by James
Watson and Francis Crick.
 The two nucleic acid chains
are bonded to each other and
held together by the hydrogen
bonds.
 Hydrogen bonds are formed
between complementary base
pairs.
A to T and G to C
RNA (Ribonucleic acid)
 It is genetic material in some plant and animal
viruses.
 It found in cytoplasm and on the membrane in
ribosome.
 Composition;
 (1) A pentose sugar  ribose
 (2) four nitrogenous bases
 (a) Purine; adenine, guanine
 (b) Pyrimidine; uracil, cytosine
 (3) phosphate group
 Structure of RNA
is similar to that
of DNA but it is
single stranded.
Types of RNA

 It is of three types
 (1) Messenger RNA:- m-RNA
 (2) Ribosomal RNA:- r-RNA
 (3) Transfer RNA:- t-RNA