Chapter–14

(b) From starch: Commercially, glucose is obtained by hydrolysis of starch by boiling it with dil. H2SO4 at
393 K under pressure.

Biomolecules
+
H
(C6 H10 O5) n + nH 2 O nC6 H12 O6
393K; 2 - 3 atm
Starch or cellulose Glucose

6. (a) Structure of Glucose: Glucose is a six carbon straight chain aldose which has one aldehydic group
(—CHO), one primary hydroxyl group (—CH2OH) and four secondary hydroxyl groups (—CHOH).
If the —OH group attached to C-5 is on the right side, the glucose is assigned D–configuration; if the
—OH group attached to C-5 is on the left side, it is assigned L–configuration. The (+) and (–) signs
represent the optical rotation as dextro and laevo, respectively and have no relationship with D and L
configuration.
CHO CHO
H OH HO H
HO H H OH

1. Biomolecules: Macromolecules which are naturally occurring in biological systems are called CHO H OH HO H
CHO
biomolecules. Examples: polysaccharides (starch, cellulose, etc.), proteins, enzymes, vitamins, hormones, H OH H OH HO H
OH H
etc.
2. Carbohydrates: These are optically active polyhydroxy aldehydes or ketones or the compounds which CH2OH CH2OH CH2OH CH2—OH
produce such units on hydrolysis, e.g., glucose, sucrose, cellulose, starch, etc. D-(+)-Glyceraldehyde
D-(+)-Glucose L-(–)-Glyceraldehyde L-(–)-Glucose
3. Classification of carbohydrates:
(a) Monosaccharides: The simple carbohydrates that cannot be broken further into smaller units on (b) Cyclic structure of glucose: The glucose has been shown to possess cyclic structure represented as
hydrolysis, e.g., glucose and fructose, ribose, etc. follows:
(b) Oligosaccharides: These are the carbohydrates which on hydrolysis give two to ten units of O
monosaccharides, e.g., sucrose, maltose, raffinose, stachyose, etc. H 1
C OH H 1
C HO 1
C H
(c) Polysaccharides: These are the carbohydrates which produce a large number of monosaccharide units 2 2 2
H OH H OH H OH
on hydrolysis, e.g., starch, cellulose, etc. O O
3 3 3
Importance of carbohydrates: HO H HO H HO H
(i) Carbohydrates act as biofuel to provide energy for functioning of living systems. H
4
OH H
4
OH H
4
OH
C6 H12 O6 + 6O 2 6CO 2 + 6H 2 O + 2832 kJ H
5
H
5
OH H
5

(ii) Carbohydrates are used as storage molecules as starch in plants and glycogen in animals. 6 6 6
CH2OH CH2OH CH2OH
(iii) D-Ribose and 2-Deoxy-D-ribose are present in RNA and DNA, respectively. α-D-(+)-Glucose β-D-(+)-Glucose

(iv) Cellulose acts as structural material of cell walls of bacteria and plants.
Haworth Structures
(v) Carbohydrates provide raw material for many important industries like textiles, paper, lacquers and
breweries. 6 CH2OH 6 CH2OH
4. (i) Reducing sugars: Those carbohydrates which contain free aldehydic or ketonic group and reduce
5 O 5 O
Fehling’s solution and Tollens’ reagent are called reducing sugars, e.g., all monosaccharides, maltose
O H H H OH
and lactose. H H
4 1 4 1
(ii) Non-reducing sugars: Those sugars which do not have free aldehydic or ketonic group and do not
reduce Fehling’s solution or Tollens’ reagent are called non-reducing sugars, e.g., sucrose. OH H OH H
HO OH HO H
3 3
2 2
5. Preparation of Glucose
Pyran
(a) From sucrose: H OH H OH
+ α-D-(+)-Glucopyranose β-D-(+)-Glucopyranose
C12 H 22 O11 + H2 O
H
C6 H12 O6 + C6 H12 O6
Sucrose Glu cos e Fructose

Biomolecules 563 564 Xam idea Chemistry–XII

 7. Reactions of Glucose (a) Ring structure of a sucrose molecule: A sucrose molecule is composed of a-glucose and b-fructose
CN units.
CH 6
OH CH2OH
(CHOH) 4 1
5 O O
H H HOH2C H
CH2OH H
4 1 2 5
Glucose cyanohydrin
OH H O H HO
HO 3 2 3 4 CH2OH
HCN 6
Glycosidic
linkage H
COOH CHO H OH OH
α-D-Glucose β-D-Fructose
HNO3 HI Sucrose
(CHOH)4 (CHOH)4 CH3 CH2 CH2 CH2 CH2 CH3
n-Hexane (b) Ring structure of a maltose molecule: A maltose molecule is composed of two a-D-glucose units in
COOH CH2OH
Saccharic acid Glucose Br which C-1 of one glucose (I) is linked to C-4 of another glucose unit (II).
wa
OH

2
ter
Acetic anhydride

6 6
2—

COOH CH2OH CH2OH

NH

5 O 5 O
CH—N—OH (CHOH) 4 H H H H
H H
4 1 4 1
(CHOH)4 CH2OH OH H OH H
Gluconic acid HO O OH
CHO 3 2 3 2
CH2OH O
Glucose oxime H OH H OH
(CH—O—C—CH3)4 α-D-Glucose α-D-Glucose
O I Maltose II
CH2—O—C—CH3
Glucose pentaacetate (c) Ring structure of a lactose molecule: A lactose molecule is composed of b-D-galactose and


b-D-glucose units.
8. Structure of Fructose: Fructose is a ketohexose and has the molecular formula C6H12O6. It belongs to
6 6
D-series and is a laevorotatory compound. CH2OH CH2OH
2 1 5 O 5 O
1 2 HO C CH2OH HO H OH
HOH2 C C OH 3
H H
4 1 4 1
3 HO H
HO H O OH H O OH H
O O 4 H 3 2 H 3 2 H
4 H OH
H OH
5 H OH H OH
5 H β-D-Galactose β-D-Glucose
H 6 Lactose
6 CH2OH
CH2OH 10. Polysaccharides: Polysaccharides are the carbohydrates which yield a large number of monosaccharide
Furan α-D-(–)-Fructofuranose β-D-(–)-Fructofuranose molecules upon hydrolysis. Starch, cellulose and glycogen are examples of polysaccharides.

The cyclic structures of two anomers of fructose are represented by Haworth structures as given below. (a) Starch: The fundamental unit of starch is a-D-glucose.
6 1 6 Structure of starch: Starch is a polymer of a-glucose and consists of two components—amylose
HOH2C CH2OH HOH2C OH and amylopectin. Amylose is a long unbranched chain with 200–1000 a-D-(+)-glucose units held by
5 2 5 2 C1–C4 glycosidic linkage.
H OH H OH
H 4 3 OH H 4 3 CH2OH 6
1 CH2OH CH2OH CH2OH
OH H OH H O 5 O O
α-D-(– )-Fructofuranose β-D-(–)-Fructofuranose H H H H H H H H H
4 1 4 1 4 1
9. Disaccharides: The sugar which on hydrolysis gives two units of monosaccharides is called disaccharide. O OH H O OH H O OH H O
Disaccharides are crystalline solids and are soluble in water. Sucrose, maltose and lactose are disaccharides.
3 2
Hydrolysis of sucrose is called inversion of cane sugar. Sucrose is a disaccharide because on hydrolysis, it H OH H OH H OH
α-Link α-Link
produces two monosaccharides namely D-(+)-glucose and D-(–)-fructose. Amylose
+
H
C12 H 22 O11 + H2 O C6 H12 O6 + C6 H12 O6 Amylopectin is a branched chain polymer of a-D-glucose units in which the chain is formed by C1–C4
Sucrose D - (+) - Glucose D - (–) - Fructose glycosidic linkage, whereas branching occurs by C1–C6 glycosidic linkage.
(disaccharide) (monosaccharide) (monosaccharide)

Biomolecules 565 566 Xam idea Chemistry–XII

 6 (a) Types of proteins based on molecular shape:
CH2OH CH2OH
(i) Fibrous proteins: They have thread-like molecules which tend to lie side by side to form fibres,
O O e.g., keratin, collagen, myosin, fibroin, etc. In such proteins, the molecules are held together by
H H H H H H
4 1 4 1
hydrogen and disulphide bonds. They are insoluble in water. They are the chief structural materials
O OH H O OH H α-Link of animal tissues.
(ii) Globular proteins: They have molecules which are folded into compact units that often form
H OH H OH O spheroidal shapes. The area of contact between molecules are small and inter-molecular forces
α-Link Branch at C6
are comparatively weak, e.g., insulin, thyroglobulin, albumin, haemoglobin and fibrinogen. In
CH2OH 6 CH2 CH2OH clotting of blood, fibrinogen gets converted into fibrous protein, fibrin.
O O O (b) Structure of Proteins: There are four levels at which the structure of proteins are studied. These are
5
H H H H H H H H H primary, secondary, tertiary and quarternary levels.
4 1 4 1 4 1
O OH H O OH H O OH H O (i) Primary structure of proteins: The sequence in which various amino acids are arranged in a
protein is called its primary structure. Any change in the sequence of amino acids creates different
protein which alters biological functions.
H OH H OH H OH
α-Link α-Link (ii) Secondary structure of proteins: It refers to shape in which a long polypeptide chain exists. A
Amylopectin protein may assume a-helix structure or b-pleated sheet structure. The a-helix structure results due
(b) Cellulose: Cellulose is a polysaccharide. The fundamental structural unit of cellulose is b-D-glucose. to regular coiling of polypeptide chain which is stabilised by intramolecular hydrogen bonding.
Keratin in hair, nails, wool and myosin in nucleus have a-helix structure. In b-pleated sheet
Structure of cellulose: Cellulose is a linear polymer of b-D-glucose which are joined by glycosidic
structure, all peptide chains are stretched to nearly maximum extension and then arranged side by
linkage between C1 of one glucose unit and C4 of the next glucose unit.
side and held together by intermolecular hydrogen bonding. Silk has b-pleated sheet structure.
HOH2C
(iii) Tertiary structure of proteins: The tertiary structure of proteins represents overall folding of the
O polypeptide chain, i.e., further folding of the secondary structure. It gives rise to two major molecular
O
shapes, viz., fibrous and globular. The main forces which stabilise 2° and 3° structures of proteins are
OH hydrogen bonds, disulphide linkages, van der Waals forces and electrostatic force of attraction.
(iv) Quaternary structure: Some of the proteins are composed of two or more polypeptide chains
HOH2C O OH referred to as sub-units. The spatial arrangement of these subunits with respect to each other is
O known as quaternary structure.
(c) Denaturation of Proteins: When a protein in its native form is subjected to a change, such as change
OH in temperature or 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
HOH2C O OH denaturation, 2° and 3° structures are destroyed but 1° structure remains intact, e.g., coagulation of egg
O
while on boiling, curdling of milk, etc.
β-links
13. (a) Enzymes: Enzymes are essential biological catalysts which are required to catalyse biological
OH reactions, e.g., maltose, lactose, invertase, etc. Almost all the enzymes are globular proteins.
Cellulose
O (b) Oxidoreductase enzymes: Enzymes which catalyse the oxidation of one substrate with simultaneous
OH reduction of another substrate.
(c) Phenylketonuria: Disease caused by deficiency of the enzyme phenylalanine hydroxylase.
11. Amino acids: Those compounds, whose molecule contains both the carboxylic acid group and the amino
group are called amino acids. There are twenty amino acids which form protein. The amino acids which (d) Albinism: Disease caused due to deficiency of an enzyme tyrosinase.
are synthesised in body are known as non-essential amino acids, e.g., glycine, alanine. Those amino acids (e) Streptokinase: Enzyme which dissolves the blood clot formed in coronary artery which leads to heart
which cannot be synthesised in body and must be obtained through diet are known as essential amino acids, trouble.
e.g., valine, lysine. 14. Nucleic Acids: Nucleic acids are long chain polymers of nucleotides. They play an important role in
Amino acids have also been classified as neutral, acidic and basic amino acids. Amino acids like glycine, transmission of hereditary characteristics and biosynthesis of proteins.
valine, etc. which contain one —NH2 and one —COOH group are called neutral amino acids. Those amino Types of nucleic acids: There are two types of nucleic acids. These are DNA and RNA.
acids such as aspartic acid, glutamic acid, etc. which contain one —NH2 group and two —COOH groups (a) Constituents of nucleic acids:
are called acidic amino acids and amino acids such as lysine, histidine, etc., which contain two —NH2 (i) Pentose sugar (ii) Phosphoric acid (iii) Nitrogenous bases.
groups and one —COOH group are called basic amino acids.
In DNA, b-D-2-deoxyribose sugar is present while in RNA b-D-ribose sugar is present.
12. Proteins are complex nitrogenous organic molecules which are essential for growth and maintenance of body. Nitrogen containing bases: There are two types of nitrogen containing bases found in nucleic acids.
O
|| These are pyrimidines and purines.
Chemically, proteins are the polymers of a-amino acids which are linked by peptide bonds (—C—NH—) . Pyrimidines: There are three bases derived from pyrimidines. These are cytosine (C), thymine (T)
and uracil (U). In DNA, T is present but in RNA, U is present.
Purines: There are two bases derived from purine. These are adenine (A) and guanine (G).

Biomolecules 567 568 Xam idea Chemistry–XII

 Nucleoside: A unit formed by the attachment of a base to 1′-position of sugar is known as nucleoside. (b) Protein synthesis: This is brought about in two steps:
HO—H 2C 5' O Base (i) Transcription: Copying of sequence of bases from the DNA strand onto the RNA molecule is
called transcription. During transcription, the double helix of the DNA partially unwinds and one
4' 1'
H H of the two DNA strands serves as a template for the synthesis of RNA strand called messenger
3' RNA (mRNA) which is complementary to a segment of the DNA chain.
H 2' H
(ii) Translation: This is the process in which mRNA directs protein synthesis in the cytoplasm of cell
OH OH with involvement of transfer RNA (tRNA) and ribosomal particles (rRNA protein complexes).
Nucleotide: When nucleoside is linked to phosphoric acid at 5′-position of sugar moiety, the unit 16. (a) Codon: The sequence of nucleotides in mRNA molecules are read in a serial order in sets of three
obtained is called nucleotide. (triplet) at a time. Each triplet is called a codon. It specifies one amino acid. The mRNA codon
O recognises the amino acids through tRNAs which carry specific amino acids.
O—P—O—H 2C
5'
O Base (b) Gene: The sequence of bases or nucleotides in the DNA molecule which regulates the synthesis of a
specific protein is called a gene. Every protein in the cell has a corresponding gene. The relationship
O 4' 1'
between a nucleotide triplet (codon) and the amino acid is called genetic code.
H H
H 3' 2' H (c) Mutation: The chemical change in the sequence of bases in the DNA molecule can lead to synthesis
of protein with an altered amino acid sequence is called mutation. This is brought about spontaneously
OH OH by exposure to UV-rays, X-rays and chemicals.
Nucleotides are joined together by phosphodiester linkage between 5′ and 3′ carbon atoms of the 17. Vitamins: Vitamins are generally regarded as organic compounds required in the diet in small amounts to
pentose sugar. perform specific biological functions for normal maintenance of optimum growth and health of the organism.
5' end of chain Vitamins are classified into two groups depending upon their solubility in fat or water:
Base
Base O (i) Fat-soluble vitamins: Vitamins A, D, E and K are soluble in fat and oils but insoluble in water. They
O 5' are stored in liver and adipose tissues.
O—P—O—CH 2 O
O—P—O—CH 2 O (ii) Water-soluble vitamins: Vitamins belonging to group B and vitamin C are soluble in water. They
O Sugar
O Sugar must be supplied regularly in diet because they are readily excreted in urine and cannot be stored
3' (except vitamin B12) in our body.
O
OH Table 14.1: Some Important Vitamins, their Sources and their Deficiency Diseases
Phosphodiester O—P—O
+ linkage S. No. Name of Vitamins Sources Deficiency Diseases
Base O Base
O 1. Vitamin A Fish liver oil, carrots, butter Xerophthalmia (hardening of cornea of eye), night
and milk blindness
O—P—O—CH 2 O 5' CH 2 O
2. Vitamin B1 (Thiamine) Yeast, milk, green Beri-beri (loss of appetite, retarded growth)
O Sugar Sugar vegetables and cereals
3. Vitamin B2 (Riboflavin) Milk, egg white, liver, Cheilosis (fissuring at corners of mouth and lips),
3'
OH OH kidney digestive disorders and burning sensation of the
3' end of chain skin.
Formation of dinucleotide
4. Vitamin B6 (Pyridoxine) Yeast, milk, egg yolk, Convulsions
(b) Deoxyribonucleic acid (DNA): It contains a pentose sugar deoxyribose, and adenine, guanine, cereals and grams
thymine and cytosine bases. A phosphate group is present at C-5 of the sugar unit. The repeating 5. Vitamin B12 Meat, fish, egg and curd Pernicious anaemia (RBC deficient in haemoglobin)
units, deoxyribonucleotides, are linked by phosphate group. Thus, they are the biopolymers of 6. Vitamin C Citrus fruits, amla and Scurvy (bleeding gums)
deoxyribonucleotides and have double helix structure of polynucleotides. The two strands of DNA (Ascorbic acid) green leafy vegetables.
are said to be complementary to each other. Adenine forms hydrogen bonds with thymine whereas
7. Vitamin D Exposure to sunlight, fish Rickets (bone deformities in children) and
cytosine forms hydrogen bonds with guanine. They are responsible for genetic characteristics and for and egg yolk osteomalacia (soft bones and joint pain in adults)
sending information and instruction in the cell for the synthesis of specific protein.
8. Vitamin E Vegetable oils like wheat Increased fragility of RBCs and muscular weakness
(c) Ribonucleic acid (RNA): It contains ribose sugar, bases from pyrimidine bases—uracil and cytosine, germ oil, sunflower oil, etc.
and two bases from purine base—adenine and guanine. A phosphate group is present at C-5 of the
9. Vitamin K Green leafy vegetables Increased blood clotting time
sugar unit. The repeating units, ribonucleotides, are linked by phosphate group. They are the polymers
of ribonucleotide and have a single helix structure. RNA is associated with the process of learning and 18. Hormones: Hormones are molecules that act as intercellular messengers. These are produced by endocrine
memory storage, and helps in biosynthesis of protein. glands in the body and are released directly in the blood stream. From here these are transported to the site
15. Functions of Nucleic Acids: Two main functions of nucleic acids are: of their action.
(a) Replication or heredity transfer: The double helix of DNA is the storehouse of the genetic Functions of hormones:
information of the organism which is contained in the sequence of bases A, T, C, G on the strands of (i) They help to maintain the balance of biological activities in the body. For example, insulin keeps the
DNA. The process by which a DNA molecule produces two identical molecules of itself in the nucleus blood glucose level within the range, epinephrine and norepinephrine mediate response to external
of the cell is called replication. stimuli, growth hormones and sex hormones play role in growth and development.

Biomolecules 569 570 Xam idea Chemistry–XII

 (ii) The hormones released by gonads are responsible for development of secondary sexual characters.
(iii) Adrenal cortex release glucocorticoids and mineralocorticoids. The glucocorticoids control the
carbohydrate metabolism, modulate inflammatory reactions and are involved in reactions to stress.
The mineralocorticoids control the level of excretion of water and salt by the kidney.

NCERT Textbook Questions

NCERT Intext Questions

Q. 1. Glucose or sucrose are soluble in water but cyclohexane or benzene (simple six-membered ring
compounds) are insoluble in water. Explain.
Ans. Glucose contains five —OH groups and sucrose (molecular mass = 342) contains eight —OH groups.
These —OH groups form hydrogen bonds with water. Because of this extensive intermolecular hydrogen-
bonding, glucose and sucrose are soluble in water.
On the other hand, benzene (molecular mass = 78) and cyclohexane (molecular mass = 84) are simple
molecules having low molecular masses. Even then they are insoluble in water as these compounds do not
contain —OH groups and hence do not form hydrogen bonds with water.
Q. 2. What are the expected products of hydrolysis of lactose? [CBSE 2019 (56/2/3)]
Ans. On hydrolysis, lactose gives two molecules of monosaccharides, i.e., one molecule of D-(+)-glucose and
one molecule of D-(+)-galactose.
+
H3 O
C12 H 22 O11 + H 2 O C6 H12 O6 + C6 H12 O6
or Lactase
Lactose D - (+) - Glu cos e D - (+) - Galactose
Q. 3. How do you explain the absence of aldehyde group in the pentaacetate of D-glucose? [CBSE 2020 (56/3/3)]
Ans. The cyclic hemiacetal form of glucose contains an —OH group at C-1 which gets hydrolysed in the
aqueous solution to produce the open chain aldehydic form which then reacts with NH2OH to form the
corresponding oxime. Therefore, glucose contains an aldehydic group. On the other hand, when glucose is
reacted with acetic anhydride, the —OH group at C-1, along with the four other —OH groups at C-2, C-3,
C-4 and C-6 form a pentaacetate. As the pentaacetate of glucose does not contain a free —OH group at C-1,
it cannot get hydrolysed in aqueous solution to produce the open chain aldehydic form and thus glucose
pentaacetate does not react with NH2OH to form glucose oxime.
CH== O 1 CHOH 1 CHOCOCH 3
2 2
H OH H OH O H OCOCH3
3 5 (CH3CO)2O 3
HO H HO H –5 CH3COOH H3COCO H
4 4
H OH H OH H OCOCH3O
OH 5 5
H H H
6
CH2OH 6 CH2OH CH2OCOCH3
Glucose α -Glucose α -Glucose pentaacetate
(open chain form) + +
β -Glucose β -Glucose pentaacetate
–H2O NH2OH

CH==NOH
NH2OH
H OH
HO H
H OH
No oxime
H OH

CH2OH
Glucose oxime

Biomolecules 571