BIOMOLECULES

I. CARBOHYDRATES
• Optically active polyhydroxy aldehydes or ketones or the compounds that produce such units
on hydrolysis.
• Since some carbohydrates are sweet, they are also called sugars or saccharides.

Types of Carbohydrates:
1) Monosaccharides: A carbohydrate that cannot be hydrolyzed further to give simpler unit.
Examples: glucose, fructose, etc.
• About 20 natural monosaccharides are known.
• Monosaccharides can be further divided as:

No. of C Atoms General Term If Aldehyde If Ketone

3 Triose Aldotriose Ketotriose
4 Tetrose Aldotetrose Ketotetrose
5 Pentose Aldopentose Ketopentose
6 Hexose Aldohexose Ketohexose
7 Heptose Aldoheptose Ketoheptose

2) Oligosaccharides: Carbohydrates that give 2–10 monosaccharides on hydrolysis.

• They can be disaccharides, tri-saccharides, etc.

3) Polysaccharides: Carbohydrates that give many monosaccharide units on hydrolysis. Examples:

starch, cellulose, glycogen, gums, etc.
• Not sweet ⇒ also called non-sugars.

4) Reducing or non-reducing sugars: Carbohydrates that reduce Fehling’s solution and Tollens’
reagent are called reducing sugars.
• All monosaccharides (both aldoses and ketoses) are reducing in nature.
• Although ketoses like fructose do not contain a –CHO group, yet they reduce Fehling’s
solution and Tollens’ reagents. This is because in alkaline medium, fructose undergoes Lobry
de Bruyn–Van Ekenstein rearrangement and gives a mixture of D-glucose, D-mannose, and
D-fructose.

GLUCOSE:
• Also called dextrose.

Methods of Preparation:
(1) By hydrolysis of sucrose in boiling HCl or H2SO4 solution:
H+
C12H22O11 + H2O → C6H12O6 (glucose) + C6H12O6 (fructose)

(2) By hydrolysis of starch in boiling H2SO4:

H+
(C6H10O5)n + n H2O → n C6H12O6 (glucose)

Structure Determination of Glucose:

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The D and L Notation:

• In the Fischer projection of a carbohydrate, if the –OH group joined to the lowermost chiral
carbon is on the right, then the compound is a D-sugar.
• If the –OH group is on the left, then the carbohydrate is an L-sugar.
• D and L are not related to the optical activity of the compound.
• D and L configurations indicate the relation of a stereoisomer with glyceraldehyde.
• Generally, natural sugars are D-sugars.
• The D- and L- forms of a carbohydrate are related as mirror images.
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Cyclic Structure of Glucose:

Limitations of open-chain structure:
• Glucose does not react with Schiff’s reagent and NaHSO3.
• The pentaacetate of glucose does not react with NH2OH, indicating the absence of free –CHO
group.
• Glucose exists in two different crystalline forms — α and β (hemiacetals). The crystallization
from conc. glucose solution at 303 K gives α- glucose (m.p. 419 K), whereas crystallization
from hot and saturated aqueous glucose at 371 K gives β-glucose (m.p. 423 K).

Mutarotation:
• Slow change in the optical rotation of a compound to an equilibrium value.
• Non-reducing sugars do not show mutarotation.
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OSAZONE FORMATION:
• Aldoses and ketoses react with 3 equivalents of phenylhydrazine to give osazones.
• Non-reducing sugars do not form osazones.
• Osazones are yellow crystalline solids with sharp melting points, so this reaction can be used
as test to distinguish between reducing and non-reducing sugars.
• The osazones of C-2 epimers (e.g., D-fructose, D-glucose, and D-mannose) are identical.
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DISACCHARIDES:
• Two monosaccharide units joined together by glycosidic linkage.
• Glycosidic linkage: An oxide linkage between two monosaccharide units formed by the loss
of a water molecule.

(1) Sucrose:
 • Contains two monosaccharide units — 𝛼-D-glucose and 𝛽-D-fructose — joined by C1–C2
glycosidic linkage.
• Since both carbonyl groups are involved in the glycosidic linkage, sucrose is a non-reducing
sugar.
• Sucrose is dextrorotatory but upon hydrolysis it gives dextrorotatory glucose and laevorota-
tory fructose. Since the laevorotation of fructose (–92.4°) is more than the dextrorotation of
glucose (+52.5°), the mixture is laevorotatory.
Since hydrolysis of sucrose results in change in the sign of optical rotation, from (+) to (–),
the product is called invert sugar.

(2) Maltose:
• Contains two 𝛼-D-glucose units joined by C1–C4 glycosidic linkage.
• Since one glucose unit can produce a free –CHO group, maltose is a reducing sugar.

(3) Lactose:
• Found in milk (2–8%), so also called milk sugar.
• Contains two monosaccharide units — β-D-galactose and β-D-glucose — joined by C1–C4
glycosidic linkage.
• Since C1 of glucose unit can produce a free –CHO group, lactose is a reducing sugar.

POLYSACCHARIDES:
(1) Starch:
• Main storage polysaccharide of plant.
• Polymer of α-D-(+)-glucose.
• Contains two components — Amylose and Amylopectin.
• Amylose:
o Is water-soluble.
o Makes up ~15–20% of starch.
o Is a linear chain of 200–1000 α-D-(+)-glucose units joined by C1–C4 glycosidic
linkage.
• Amylopectin
 o Is insoluble in water.
o Makes up ~80–85% of starch.
o Is a branched chain of α-D-glucose units joined by C1–C4 glycosidic linkage whereas
branching occurs by C1–C6 glycosidic linkage.

(2) Cellulose:
• Makes up cell wall of plant cells.
• Is a straight chain of β-D-glucose units joined by C1–C4 glycosidic linkage.

(3) Glycogen:
• Main storage polysaccharide of animals.
• Also called animal starch because it’s structurally similar to amylopectin but is more
branched.
• Present in liver, muscles, brain and in yeast and fungi.

TESTS FOR CARBOHYDRATES:

Test: Given by Reagent Observation Image

Molisch's reagent
All carbohydrates purple ring at the
Molisch’ (α-naphthol in
having 5 or more interface of two
test: ethanol) and then
carbon atoms layers
conc. H2SO4
 Ketoses: red
Seliwanoff’s Ketoses (aldoses Resorcinol and
Aldoses: faint
test: react slowly) conc. H2SO4
pink

brick-red
Barfoed’s Copper(II) acetate
Monosaccharides precipitate (due to
test: in acetic acid
Cu2O)
Note: D-glucose forms 5-(hydroxymethyl)furfural in Molisch’s test and then combines with 2 eq. of
α-naphthol to give purple coloration.

II. VITAMINS
• Organic compounds needed in small amounts (micronutrients) for specific biological
functions and optimum growth of organisms.

Types of Vitamins:
(1) Fat-soluble:
• Vitamins A, D, E and K.
• Stored in liver and adipose tissues.

(2) Water-soluble:
• Vitamin C and B-group vitamins.
• Must be supplied regularly in diet because they are excreted in urine and cannot be stored
(except vitamin B12) in our body.

Vitamin Sources Deficiency Diseases

Fish liver oil, carrots, Xerophthalmia (hardening of cornea),
A
butter, and milk night blindness
Yeast, milk, green
B1 (thiamine) Beri beri (loss of appetite, retarded growth)
vegetables, and cereals
Cheilosis (fissuring at corners of mouth
Milk, egg white, liver,
B2 (riboflavin) and lips), digestive disorders and burning
kidney
sensation of the skin
Yeast, milk, egg yolk,
B6 (pyridoxine) Convulsions
cereals, and grams
B12 (cobalamin) Meat, fish, egg, and curd Pernicious anaemia (RBC deficiency)
Citrus fruits, amla, and
C (ascorbic acid) Scurvy (bleeding gums)
green leafy vegetables
Rickets (bone deformities in children) and
Fish, egg yolk, and
D osteomalacia (soft bones and joint pain in
exposure to sunlight,
adults)
Wheat germ oil, Increased fragility of RBCs and muscular
E
sunflower oil weakness
K Green leafy vegetables Increased blood-clotting time

III. NUCLEIC ACIDS (DNA & RNA)

• Also called polynucleotides.
• Complete hydrolysis of DNA (or RNA) gives:
o A pentose sugar: 𝛽-2-deoxyribose for DNA and 𝛽-D-ribose for RNA
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o H3PO4
o Nitrogen-containing heterocyclic compounds (called bases).

• The bases present in DNA are adenine (A), guanine (G), cytosine (C), and thymine (T).
• The bases present in RNA are adenine (A), guanine (G), cytosine (C), and uracil (U).
• Adenine and guanine are purines, whereas cytosine, thymine, and uracil are pyrimidines.

pyrimidine cytosine thymine uracil

Structure of Nucleic Acids:

Nucleoside: A 5-carbon sugar (deoxyribose or ribose) having a nitrogenous base joined to 1′ position
(C1).

Nucleotide: A 5-carbon sugar having a nitrogenous base at 1′ position and a phosphate unit at 5′
position.

Nucleoside Nucleotide Dinucleotide

Phosphodiester linkage: Formed when the phosphate unit of C5′ of one nucleotide unit is joined to
the C3′ position of another nucleotide. The resulting unit is called a dinucleotide.

The primary structure of a nucleic acid refers to the sequence of the nucleotides (nitrogenous bases)
in a strand.

The secondary structure of DNA (by Watson and Crick) consists of two polynucleotide chains wound
about each other to form a right-handed double helix.
• One chain runs from 3′ to 5′ and the other chain runs from 5′ to 3′ (antiparallel to each other).
• These chains are held together by hydrogen bonds between pairs of bases — A = T (2 H
bonds) and C ≡ G (3 H bonds).
• Thus, hydrogen bonding is responsible for the stability of DNA.
• The two strands in DNA are complementary to each other since the sequence of bases in one
strand fixes the sequence of bases in the other strand.
 Hydrogen bonding in the bases present in DNA

In the secondary structure of RNA, the single stranded can fold back on itself.
• Based on their functions, RNA molecules are of 3 types: messenger RNA (m-RNA),
ribosomal RNA (r-RNA) and transfer RNA (t-RNA).

DNA Fingerprinting: The sequence of bases on the DNA of a person — unique and cannot be
altered.
• DNA fingerprinting is used to identify individuals, paternity, and racial groups to rewrite
biological evolution.

IV. HORMONES
• Produced by endocrine glands and poured directly in the blood stream.
• Can be steroids (estrogens and androgens), polypeptides (insulin and endorphins) and amino
acid derivatives (epinephrine and norepinephrine).
• Insulin and glucagon regulate the blood glucose level.
• Epinephrine and norepinephrine mediate responses to external stimuli.
• Thyroxine (produced in the thyroid gland) is an iodinated derivative of amino acid tyrosine.
• Iodine deficiency leads to thyroxine deficiency that causes hypothyroidism and its excess
causes hyperthyroidism.
• Glucocorticoids control the carbohydrate metabolism, modulate inflammatory reactions, and
are involved in reactions to stress.
• Mineralocorticoids control the level of excretion of water and salt by the kidney.
• Malfunctioning of adrenal cortex leads to Addison’s disease (hypoglycemia, weakness, and
increased susceptibility to stress).
• Testosterone is the major sex hormone in males and estradiol in females.
• Progesterone prepares the uterus for implantation of fertilized egg.

V. PROTEINS
• Polymers of 𝛼-amino acids; also called polypeptides.
• Needed for growth and maintenance of body.

The Isoelectric Point (pI):

• The pH at which an amino acid has no net charge or
• The pH at which the total positive charge on an amino acid is equal to the total negative
charge.
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Tests for Proteins:

Test: Given by Reagent Observation Image

Peptide bonds Aq. NaOH / KOH

Biuret test: (–CO–NH–, and then aq. purple solution
e.g., urea) CuSO4

color changes
Xanthoproteic Conc. HNO3 and
Proteins from yellow to
test: then NaOH
orange

Ninhydrin Amino acids deep blue to

ninhydrin
test: except proline purple