chemistry

BIOMOLECULES
Sakshi Vora

IIT - Roorkee

10th, 12th CBSE State Topper

7+ Years of Teaching Experience

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Biomolecules
carbohydrates
Carbohydrates

Carbohydrates (hydrates of carbon) are naturally occurring

compounds having general formula Cx(H2O)y, which are constantly
produced in nature and participate in many important biochemical
reactions.
Modern Concept :
Carbohydrates are polyhydroxy aldehyde or ketone or
Substances which yield these (Polyhydroxy aldehyde or ketone) on
hydrolysis

H2O/H+
● Carbohydrates Polyhydroxy aldehyde or ketone.
● Carbohydrates are known as Saccharides.
Classification
Classification of carbohydrates :
Monosaccharides : (Simple sugars)
These are the sugars which cannot be hydrolysed into smaller
molecules.
General formula is CnH2nOn
Ex. - Glucose, Fructose, Ribose

● If aldehyde group is present in monosaccharide, then it is

known as aldose.
● If ketone group is present in monosaccharide, then it is known
as ketose.
Oligosaccharides :-
These are the sugars which yields 2 - 10 monosaccharides units on
hydrolysis. Such as.

These are of following types.

(a) Disaccharides :- Gives two monosaccharide unit on hydrolysis

(may or may not be same).
Ex. Sucrose, Maltose, Lactose
(a) Trisaccharides :- Gives Three monosaccharide unit on
hydrolysis.
Polysaccharides :-
These are the non sugars which yield a large no of monosaccharide
units on hydrolysis General formula - (C6H10O5)n.
Ex. Starch, Cellulose, Glycogen
stereochemistry
Stereochemistry of
carbohydrates :

D & L - sugars :

Smallest Carbohydrate
D aldoses
The D-family
aldoses
The D-family
aldoses
epimers
Epimers :
A pair of diastereomers that differ only in the configuration about a
single carbon atom are said to be epimers. D(+) - glucose is
epimeric with D(+)- mannose and D(+) - galactose.
anomers
Anomers :
Anomers are the stereoisomers which differs at a single chiral
centre out of many and are ring chain tautomer of the same open
chain compound.
Anomers :

36% α - D -glucose, 63.8 % β-D-glucose and 0.2 % open chain form.

C1 Carbon is known as anomeric carbon.
Haworth projection
Haworth projection :
Chair forms of α and β D-Glucose :
mutarotation
Mutarotation :
Mutarotation :

Mutarotation occurs first by opening of the pyranose ring to the

free aldehyde form.
fructose
Structure of fructose
Structure of fructose
Reactions of glucose
Reactions of Glucose
Acetylation :
Reaction with NH2-OH (hydroxyl amine):
Reaction with phenylhydrazine :
Both glucose and fructose give “osazone’.
Reaction with glucose :
Catalytic reduction :
Oxidation :
Practise questions
Number of stereocenters present in linear and cyclic structures of glucose
are respectively.

A. 5 & 4
B. 4 & 4
C. 5 & 5
[Main April 10, 2019 (II)]
D. 4 & 5
Which of the following statements is correct

A. Gluconic acid can form cyclic (acetal/hemiacetal) structure

B. Gluconic acid is a dicarboxylic acid
C. Gluconic acid is a partial oxidation product of glucose
D. Gluconic acid is obtained by oxidation of glucose with HNO3

[Main Jan. 07, 2020 (II)]

Which of the following statement is not true for glucose?

A. Glucose exists in two crystalline forms

B. Glucose gives Schiff's test for aldehyde [Main Jan. 08, 2020 (1)]
C. Glucose reacts with hydroxylamine to form oxime
D. The pentaacetate of glucose does not react with hydroxylamine to
give oxime
Glucose on prolonged heating with HI gives

A. n-Hexane
B. 1- Hexene
C. Hexanoic acid
[Main 2019]
D. 6-iodohexanal
Consider the following reactions

[Main Sep. 02, 2020 (1)]

‘x’ , ‘y’ and ‘z’ in these reactions are respectively.

A. 5, 4 & 5
B. 4, 6 & 5
C. 4, 5 & 5
D. 5, 6 & 5
important carbohydrates
sucrose
Sucrose :

(C12H22O11) : ⟶ A dimer of

C1 α - D-Glucose & C2 β-D-Fructose.

● It is white, crystalline & sweet substance soluble in water
obtained from the sugar cane.
● When heated above its melting point. It forms a brown
substance known as caramel.
● It’s aqueous solution is dextrorotatory [α]D = +66.5o
Sucrose :
Hydrolysis of sucrose brings about a change in the sign of rotation,
from dectro (+) to leavo (-) & such a change is known as inversion of
sugar and the mixture obtained on acidic hydrolysis is known as invert
sugar.
Structure of sucrose
Important points

● Sucrose is non - reducing sugar because it has stable acetal

linkage & in aq. solution it does not give free carbonyl group
and so it does not reduces Tollen’s & Fehling’s solution.

● This indicates that neither the aldehyde group of glucose nor

the ketonic group of fructose is free in sucrose.
Practise questions
Which of the following statements is not true about sucrose?

A. It is a non reducing sugar

B. The glycosidic linkage is present between C1 of α-glucose and C1 of β-
fructose
[Main April 9, 2019 (1)]
C. It is also named as invert sugar
D. On hydrolysis, it produces glucose and fructose
The number of chiral carbons present in sucrose is ________.

[Sept. 05, 2020 - II]

MALtose
Maltose :
(C12H22O11) : ⟶ A dimer of

C1 α - D-Glucose & C4 α -D-Glucose.

It is obtained by partial hydrolysis of starch by the enzyme diastase

present in malt i.e., sprouted barley seeds.
Maltose :

● Maltose is a reducing sugar since it reduces Tollen’s reagent

and Fehling’s solutions
Haworth Projection Formulae of α-D-Maltose
Practise questions
What are the functional groups present in the structure of maltose?

A. One ketal and hemiketal

B. Two acetals
C. One acetal and one hemiacetal [Main Sep. 04, 2020 (1)]
D. One acetal and one ketal
lactose
Lactose (Milk sugar) C12H22O11

(C12H22O11) : ⟶ A dimer of

C1 - D-β Galactose & C4 β -D-Glucose.

● Lactose occurs in milk
● Lactose on hydrolysis with dilute acid or by enzyme lactase,
yields an equimolar mixture of D-glucose and D-galactose.
● It is a reducing sugar it reduces Tollen’s or Fehling’s solution.
Lactose (Milk sugar) C12H22O11
Practise questions
A.

B.
C.
D.

[Sep. 06, 2020 (II)]

starch
Starch (C6H10O5)n

It is the chief food reserve material or storage polysaccharide of

plants and is found mainly in wheat, maize, rice, potatoes, barley,
bananas

Composition :
Starch is not a single compound but is a mixture of two
components - a water soluble component called amylose (10-20%)
and a water insoluble component called amylopectin (80 - 90%).
Both amylose and amylopectin are polymers of α-D-glucose.
Properties :
(i) Starch is a white amorphous powder sparingly soluble in water.
Its aqueous solution gives a blue colour with iodine solution due
to the formation of an inclusion complex.

(ii) Starch is a non - reducing saccharide. It neither reduces Tollen’s

reagent or Fehling’s solution
Structure of amylose :
Amylose is water soluble and gives blue colour with iodine solution.
It is a linear polymer of α-D-glucose in which C1 of one glucose unit
is attached to C4 of the other through α - glycosidic linkage.

C1 α - D-Glucose & C4 α -D-Glucose.

Structure of amylopectin :

C1 α - D-Glucose & C4 α -D-Glucose + C1-C6

Nucleic acids
Nucleic Acids :

The particles in nucleus of the cell, (chromosomes) responsible for

heredity, are made up of proteins and another type of biomolecules
called nucleic acids.

These are mainly of two types, the deoxyribonucleic acid (DNA) and
ribonucleic acid (RNA).

Since 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 pentose sugar,

phosphoric acid and nitrogen containing heterocyclic compounds
(called bases).

In DNA molecules, the sugar moiety is β-D-2-deoxyribose whereas

in RNA molecule, it is β-D-ribose.
Different Bases in Nucleic Acids :

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).
Structure of nucleic acid
Structure of Nucleic Acids :

A unit formed by the attachment of a base to 1’ position of sugar is

of known as nucleoside.

In nucleosides, the sugar carbons are numbered as 1’, 2’, 3’. etc. in
order to distinguish these from the bases.

When nucleoside is linked to phosphoric acid at 5’ - position of sugar

moiety, we get a nucleotide.
Structure of Nucleic Acids :
Structure of Nucleic Acids :

Nucleotides are joined together by phosphodiester linkage between

5’ and 3’ carbon atoms of the pentose sugar.
Practise questions
Among the following compounds, which one is found in RNA?

A. C. [Main jan 11, 2019 (I)]

B. D.
dinucleotides
Formation of dinucleotide :

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 hydrogen bonds with thymine whereas cytosine

forms hydrogen bonds with guanine.
Formation of dinucleotide :

In secondary structure of RNA, helices are present which are only

single stranded.
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).
Which of the following statements is not true about RNA?

A. It controls the synthesis of protein.

B. It has always double stranded helix structure. [Main April 12, 2019 (1)]
C. It usually does not replicate.
D. It is present in the nucleus of the cell.
Amino acids
Amino Acids
Bifunctional compounds having an acidic carboxylic group and a
basic amino group
There are 20 amino acids commonly found in proteins and are
standard amino acids. All are α amino acids.
Amino Acids
All amino acids are chiral molecules with at least one chiral carbon
(except glycine, H3N⊕CH2COO-).
Except Glycine all other amino acids optically active & can be
assigned D & L configuration.
Classification of aa
Classification of Amino acids
Classification of Amino Acids

Occurrence Requirement Chemical Nature

Natural Essential Neutral

Synthetic Non Essential Acidic

Semi Essential Basic

Based on Requirement
1. Essential amino acids cannot be synthesized in human body so
dietary intake is required.
2. Semi essential amino acids can be synthesized in human body
but dietary intake is required during growing stages (when
more of cell division is required)
3. Non essential amino acid - Body can synthesize them.
Based on chemical nature
● Neutral - Amino acid having equal number of NH2 and COOH

● Acidic - Amino acid having more COOH than NH2 group.

● Basic -Amino acid having more NH2 than COOH group.

List of amino acids
Different Amino Acids
Different Amino Acids
Different Amino Acids
Different Amino Acids
Different Amino Acids
Different Amino Acids
Practise questions
Thiol group is present in:

A. Cysteine
B. Methionionine
[Main, 2016]
C. Cytosine
D. Cystine
A tetrapeptide has –COOH group on alanine. This produces glycine
(Gly), valine (Val), phenylalanine (Phe) and alanine (Ala), on
complete hydrolysis. For this tetrapeptide, the number of possible
sequences (primary structures) with —NH2 group attached to a chiral
center is
[Adv.2013]
The number of Groups present in a tripeptide Asp-Glu-Lys

is__________

[Main Spe.03, 2020 (II)]

Zwitterions
Amino acids as dipolar ions as zwitterion
Glycine has Ka = 1.6 x 10-10 and Kb = 2.5 x 10-12, whereas most carboxylic
acids have Ka values of about 10-5 and most aliphatic amines have kb
values of about 10-4 .
All these properties are quite consistent with a dipolar ion structure for
the amino acids (I)

Amino acids: dipolar ions (Zwitterion)

Amino acids as dipolar ions as zwitterion
When the solution of an amino acid is made alkaline, dipolar ion (I) is
converted into the anion (II).
Isoelectric point of aa
Isoelectric point of amino acids
Isoelectric point of amino acids
The isoelectric point (pI) is the pH at which the amino acid exists only as
a dipolar ion with net charge zero.
For glycine, for example, the isoelectric point is at pH 6.1.
Practise questions
 Which of the following will not exist in zwitterionic form at pH = 7?

A.

B.
[Apr. 15, 2018 - I]

C.

D.
The structure of a peptide is given below.

[Adv.2020]

If the absolute values of the net charge of the peptide at pH = 2, pH = 6, and pH

= 11 are |z1|, |z2l, and |z3|, respectively, then what is |z1| + |z2| + |z3|?
peptides
Peptide
A peptide is a kind of amide formed by intermolecular reaction of the
amino group of one amino acid and the carboxyl group of a second amino
acid.
Naming of dipeptide

By convention, the amino acid with free amino group (N-terminal) is

written at the left end and the one with the unreacted carboxyl group (C-
terminal) at the right end.
proteins
Polypeptides and proteins
A polypeptide with more than hundred amino acid residues, having
molecular mass higher than 10,000 is called a protein.
Types of Proteins
Proteins can be classified into two types on basis of their molecular shape.

● 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.
Types of Proteins
Proteins can be classified into two types on basis of their molecular shape.

● 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.
STRUCTURE OF proteins
Structure of proteins
● Primary structure of proteins :

● Each polypeptide in a protein has amino acids linked with each other
in a specific sequence and it is this sequence of amino acids that is
said to be the primary structure of the protein.

● Any change in this primary structure i.e., the sequence of amino acids
creates a different protein.
Structure of proteins
● 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. a-helix
and a-pleated sheet structure.
Structure of proteins

α - Helix structure of proteins

α - Helix : a polypeptide chain forms all possible hydrogen bonds by

twisting into a right handed screw (helix) with the -NH group of each
amino acid residue hydrogen bonded
to the Of an adjacent turn of the helix.
Structure of proteins
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.
Structure of proteins
➔ 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.
The main forces which stabilise the 2° and 3° structures of proteins
are hydrogen bonds, disulphide linkages, van der waals and
electrostatic forces of attraction.
Structure of proteins
➔ 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. Example : Hemoglobin,
Chlorophyll.
vitamins
Vitamins :
Vitamins :
Vitamins :
NOTE :
Vitamin - D , E , K , A are fat soluble vitamins.
Vitamin - B , C are water soluble vitamins.
Vitamins :
Practise questions
Which of the vitamins given below is water soluble?

A. Vitamin E
B. Vitamin K
[Main, 2015]
C. Vitamin C
D. Vitamin D
 Match the following

(i) Riboflavin a. Beriberi

(ii) Thiamine b. Scurvy [Main, jan. 07 2020 (I)]

(iii) Pyridoxine c. Cheilosis

(iv) Ascorbic acid d. Convulsions

A. (i) - (a), (ii) – (d), (iii) – (c), (iv) – (b)

B. (i) – (c), (ii) – (d), (iii) – (a), (iv) – (b)
C. (i) – (c), (ii) – (a), (iii) – (d), (iv) – (b)
D. (i) – (d), (ii) – (b), (iii) – (a), (iv) – (c)
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