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Dr. S Nayak
CHEMISTRY OF CARBOHYDRATES
Organic substances with C, H and O in the
ratio of 1:2:1. (C6H12O6)
Polyhydroxy aldehyde or ketone derivatives.
1] Monosaccharides.
Simple sugars & cannot be hydrolysed further.
Further classified on the basis of number of
carbon atoms and the presence of functional
groups.
Dr. S Nayak
Carbon atoms
Trioses (3 carbon)
Examples
Functional groups
Glyceraldehyde
Aldehyde (aldotriose)
Dihydroxy acetone Ketone (Ketotriose)
Aldehyde (aldotetrose)
Aldehyde(Aldopentose)
Aldehyde(Aldopentose)
Ketone (Ketopentose)
Aldehyde (Aldohexose)
Aldehyde (Aldohexose)
Ketone (Ketohexose)
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2] Disaccharides.
With two molecules of same or different
monosaccharide units.
Give two monosaccharide units on hydrolysis .
Monosaccharide units are joined by glycosidic bond.
Examples
Product formed
Upon hydrolysis
Maltose
glucose + glucose
Lactose
galactose + glucose
Sucrose
glucose + Fructose
Isomaltose glucose + glucose
Glycosidic
Linkage
1-4
1-4
1-2
1-6
Sources
Malt
Milk
Sugar cane
Digestion of
amylopectin
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3] Oligosaccharides
4] Polysaccharides
a)
Homopolysaccharide:
Polymer of same monosaccharide units
Examples
Starch
Dextrin
Glycogen
Cellulose
Inulin
Chitin
Monosaccharide Unit
Glucose
Glucose
Glucose
Glucose
Fructose
N-acetyl glucosamine
Sources
Plant, rice
from starch hydrolysis
liver, muscle
Plant fibers
dahlia roots
Shells of arthropod
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Starch:
Is a mixture of two polysaccharides, 1) Amylose
and 2) Amylopectin.
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Amylopectin
15-20%
80-85%
2. Structure
Unbranched, linear
Highly branched.
3. Molecular Weight
60 kDa
500 kDa
4. Linkage
5. Reaction with
Iodine solution
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Glycogen
Dextrin
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Inulin
Consists of a small number of D-fructose joined by
2-1 glycosidic linkages
It is used to measure the glomerular filtration rate, a
test to assess the function of kidney.
b) Heteropolysaccharide
They are polymer of different monosaccharide
units or their derivatives
E.g. Mucopolysaccharides (MPS) and blood group
substances
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ISOMERISM IN CARBOHYDRATES
The presence of asymmetric carbon atoms (A
carbon atom to which four different atoms or
groups attached is known as asymmetric
carbon) in a compound produces following
effect;
Sterioisomerism of the compound
Confers optical activity to the compound.
1. Sterioisomerism
Compounds which are identical in composition
and structural formula but differ in spatial
configuration are called as sterioisomers.
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a. Enantiomer:
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b. Anomerism
Sugars in solution exist in ring form and not in straight chain
form.
Aldosugar form mainly pyranose ring structure
Ketosugar form furanose ring structure
Carbon 1, after ring formation becomes asymmetric and it is
called as anomeric carbon atom. If the two sugars which differ
in the configuration at only C1 in case of aldoses and C2 in
ketoses are known as anomers and represented as alpha and
beta sugars.
E.g. -D glucose and -D-glucose
-D fructose and -D-fructose
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c. Epimerism:
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2. Optical activity
The compounds having asymmetric carbon atoms can
rotate the beam of plane polarized light and are said to
be optically active.
An isomer which can rotate the plane of polarized
light to the right is called as dextrorotatory and is
designated as (d) or (+)
Example: D- (d)-glucose or it is also known as
dextrose.
While the isomer which rotates the plane of polarized
light to left is known as levorotatory, and is identified
as (l) or (-).
Example: D-(l)-fructose.
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Reduction tests
Due to the presence of a free aldehyde or ketone
group, carbohydrates are readily oxidised and
behave as the reducing agents. These sugars
have the capacity to reduce cupric ion (Cu2+) to
cuprous ion (Cu+). Therefore the reducing
sugar like glucose will give positive Benedicts
reactions.
In case of sucrose (non-reducing sugar), the
aldehyde group of glucose and keto group of
fructose are linked. It gives positive test when it
gets hydrolysed to glucose and fructose.
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2.
3.
4.
5.
22
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Glycosides
Glycosides are compounds containing a
carbohydrate and a non carbohydrate residue in a
same molecule linked together by a glycosidic
bond.
Cardiac glycosides:
Digitoxin or digoxin stimulates muscular
contraction (cardiac stimulant).
Streptomycin-antibiotic used in treatment of
tuberculosis.
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Case 1
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Lactose Intolerance
Cause: A deficiency of the brush border enzyme
lactase
If lactose is not cleaved, it cannot be absorbed, so it
makes its way down the drain from the small into
the large intestine. Many of the bacteria found there
have the capacity to metabolize lactose, which they
convert to acids and gas. This leads to abdominal
discomfort and diarrhea
Since the environment in the large intestine lacks
oxygen, hydrogen (H2) generated in the bacterial
fermentation is not oxidized but instead released as
such, and in part is exhaled