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Biomolecules
1. Definition of carbohydrates: Polyhydroxy aldehydes or polyhydroxy ketones or compounds which
give these on hydrolysis.
2. Classification of carbohydrates
a. Monosaccharides
Simplest carbohydrates
Cannot be hydrolysed into simpler compounds
Examples: Glucose, mannose
b. Oligosaccharides
Carbohydrates which give 210 monosaccharide units on hydrolysis
Examples: Sucrose, Lactose, Maltose
c. Polysaccharides
Carbohydrates which give a large number of monosaccharide units on hydrolysis
Examples: Cellulose, starch
3. Anomers
Pairs of optical isomers which differ in configuration only around C 1 atom are called anomers.
Examples: -D-glucopyranose and -D-glucopyranose
4. Epimers
Pairs of optical isomers which differ in configuration around any other C atom other than C 1 atom are
called epimers. Examples: D-glucose and D- mannose are C2 epimers.
H
C12H22O11 H2O
C6H12O6 C6H12O6
Sucrose
Glucos e
Fructose
b. From starch:
C6H10O5 n nH2O
393K ;2 3 atm
Sucrose
or
cellulose
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nC6H12O6
Glucos e
CHEMISTRY BIOMOLECULES
COOH
HNO3
Glucose
(C HOH)4
|
COOH
Saccharic acid
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CHO
|
5(CH3CO)2 O
ZnCl2
Glu cos e
(C HOCOCH3 )4 5 CH3COOH
Shows the presence
|
CH2OCOCH3
of 5 OH groups
Glucose does not give Schiffs test and does not react with sodium bisulphite and NH 3.
Pentaacetyl glucose does not react with hydroxyl amine. This shows the absence of the CHO group and
hence the presence of the ring structure.
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Glucose and fructose give the same osazone because the reaction occurs at C 1 and C2 only.
10. Lobry de Bruyn Van Ekenstein Rearrangement
CHO
|
H C OH
|
NaOH
CO
|
CHO
NaOH
HO C H
|
H C OH
||
C OH
|
(CHOH)3
(CHOH)3
(CHOH)3
(CHOH)3
C H2OH
C H2OH
C H2OH
C H2OH
D-Fructose
D-Mannose
ene diol
D-Glucose
CH2OH
Same results are obtained when fructose or mannose is reacted with an alkali.
It is because of the formation of the enediol intermediate.
It explains why fructose acts as a reducing sugar.
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11. Mutarotation
The spontaneous change in specific rotation of an optically active compound is called mutarotation.
Example: -D-glucose (MP = 146C) with specific rotation []D = +111 and -D-glucose (MP = 150C)
with specific rotation []D =+19.2. When either form is dissolved in water and allowed to stand, the
specific rotation of the solution changes slowly and reaches a constant value of +52.5.
-D-glucose
-D-glucose
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H2O
C6H12O6
D glucose
[]D = +52.5
C6H12O6
D fructose
[]D = 92.4
Sucrose is a non-reducing sugar because the two monosaccharide units are held together by a
glycosidic linkage between C1 of -glucose and C2 of -fructose. Because the reducing groups of
glucose and fructose are involved in glycosidic bond formation, sucrose is a non-reducing sugar.
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15. Maltose
Maltose is composed of two -D-glucose units in which C1 of one glucose is linked to C4 of another
glucose unit. The free aldehyde group can be produced at C1 of second glucose in solution and it
shows reducing properties so it is a reducing sugar.
Maltose: Maltose
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H O
Glucose + Glucose
C1 C1
CHEMISTRY BIOMOLECULES
H O
Glucose +
Glucose
C4 C1
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17. Starch
It is a polymer of -glucose and consists of two componentsAmylose and Amylopectin.
Amylose
Amylopectin
Water-soluble component.
Water-insoluble component.
NH2
COOH
NH2
[D]
H2N
[L]
19. Essential amino acids: The amino acids which cannot be synthesised in the body and must be
obtained through the diet are known as essential amino acids. Examples: Valine, Leucine
20. Non-essential amino acids: The amino acids which can be synthesised in the body are known as
non-essential amino acids. Example: Glycine, Alanine
21. Zwitterion form of amino acids: Amino acids act like salts rather than simple amines or carboxylic
acids. This behaviour is due to the presence of both acidic (carboxyl group) and basic (amino group)
groups in the same molecule.
In aqueous solution, the carboxyl group can lose a proton and the amino group can accept a proton,
giving rise to a dipolar ion known as a zwitterion. This is neutral but contains both positive and
negative charges.
In zwitterionic form, amino acids show amphoteric behaviour as they react with both acids and bases.
R C H COOH
|
NH3
OH
R C H COO
NH3
OH
R C H COO
|
NH2
zwitter ion
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CHEMISTRY BIOMOLECULES
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CHEMISTRY BIOMOLECULES
Two shapes are possible:
Fibrous proteins
Globular proteins
28. Quaternary structure of proteins: Some 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 of proteins.
29. Denaturation of proteins
The loss of biological activity of proteins when a protein in its native form is subjected to physical
change like change in temperature or chemical change like change in pH. This is called denaturation
of protein. Examples: Coagulation of egg white on boiling, curdling of milk
30. Nucleoside
Base + sugar
31. Nucleotide
Base + sugar + phosphate group
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Water-soluble vitamins
These vitamins are soluble in water.
Water-soluble vitamins must
be supplied regularly in the diet because
they are readily excreted in urine and
cannot be stored (except vitamin B12) in
our body.
Examples: Vitamins B and C
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CHEMISTRY BIOMOLECULES
37. Important vitamins, their sources and their deficiency diseases
Name of vitamin
Vitamin A
Source
Fish liver oil, carrots,
butter and milk
Vitamin B1
(Thiamine)
Vitamin B2
(Riboflavin)
Vitamin B6
(Pyridoxine)
Vitamin B12
Vitamin C
(Ascorbic acid)
Vitamin D
Vitamin E
Vitamin K
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Deficiency diseases
Xerophthalmia
(hardening of the cornea of the
eye)
Night blindness
Beriberi (loss of appetite,
retarded growth)
Cheilosis (fissuring at
the corners of mouth and
lips), digestive disorders
and burning sensation
of the skin
Convulsions
Pernicious anaemia
(RBC deficient in
haemoglobin)
Scurvy (bleeding gums)
Rickets (bone deformities
in children) and osteomalacia
(soft bones and
joint pain in adults)
Increased fragility of
RBCs and muscular
weakness
Increased blood clotting
time
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