Carbohydrates

2020-2021
Dr. Salm K. Mohammed
Ph.D. of Clinical Biochemistry
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Introduction
• A carbohydrate is an organic molecule
consisting of carbon (C), hydrogen (H)
and oxygen (O) atoms, occurring in
foods and living tissues such as sugars,
starch, and cellulose. Typically can be
broken down to release energy in the
animal body.
• Usually polyhydroxyaldehydes or
polyhydroxyketones or substances that
hydrolyze to yield carbohydrates.
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• Simple carbohydrates are known as
sugars or saccharides (Latin saccharin)
and the ending of the names of most
sugars is (-ose).
• They widely distributed in plants and
animals; they have important structural
and metabolic roles.
• In plants produced by photosynthesis.
• In animal cells serves as an important
source of energy for vital activities.
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Classification
1. Monosaccharides: are simple sugars
and can’t be further hydrolyzed.
Monosaccharides are subdivided into
different types based on the functional
group and number of carbon atoms.

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2. Disaccharides:
Yield two molecules of monosaccharides
when hydrolyzed, examples are sucrose,
lactose and maltose.
3. Oligosaccharides:
Yield 3-10 monosaccharide units on
hydrolysis.
4. Polysaccharides:
Yield more than ten molecules of
monosaccharides on hydrolysis, examples
are starch, dextrin, glycogen and cellulose.
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 Polysaccharides

• Subdivided into:
HOMO polysaccharides (all one type of
monomer): glycogen, starch, cellulose
and chitin.
HETERO polysaccharides (different
types of monomers): agar,
peptidoglycans and glycosaminoglycans

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1. Starch:
• Is formed of an alpha glycosidic chain.
• Yielding only glucose on hydrolysis.
• Is the most important food source of
carbohydrate and is found in cereals, potatoes,
legumes and other vegetables.
• Natural starch is insoluble in water.
There are two forms of starch:
 Amylose: linear polymer of alpha (1-4) linked
glucose residues.
 Amylopectin: branched polymer of alpha (1-4)
linked glucose residues with alpha (1-6) linked
branches. 11
2. Glycogen:

• Is the polysaccharide of the animal body.

• It is branched structure with branched
polymer of alpha (1-4) linked glucose
residues with alpha (1-6) linked
branches like amylopectin but even more
highly branched and more compact.

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3. Inulin:
• Is a long chain homoglycan composed
of D-fructose units with repeated beta
(1-2) linkages, found in tubers and
roots such as onions and garlic .

4. Dextrins:
• Are substances which are formed in
the course of partially hydrolytic
breakdown of starch.
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5. Cellulose:

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6. Chitin:

• Is an important structural,
polysaccharide of exoskeleton of
insects also found in the shells of
arthropods.
• Structurally, chitin apparently consists
of N-acetyl-glucosamine units joined by
beta (1-4) glycosidic linkages.

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Isomerism
• Isomers are molecules that have the
same molecular formula, but have a
different arrangement of the atoms in
space (different structures).
• Such as fructose, glucose, mannose and
galactose are isomers of each other
having formula [C6H12O6].
Structural isomerism
Stereoisomerism
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Structural isomerism:
Same molecular formula, but differ from each
other by having different structures.

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Stereoisomerism
• Same molecular formula and Same structure,
but they differ in spacial configuration.
Asymmetric (chiral) carbon atoms (A carbon
linked to four different atoms or groups
farthest from the carbonyl carbon) allows the
formation of stereoisomerism.

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The possible stereoisomerism depends
on the number of asymmetric carbons.

Enantiomers Optical
Isomerism Isomerism

Epimerism Anomerism
Isomerism Isomerism

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Enantiomers:
• Non-Super imposable COMPLETE mirror
image (differ in configuration at EVERY
CHIRAL CENTER).
• The two members of the pair are
designated as D and L forms.
• In D form the OH group on the
asymmetric carbon is on the right.
• In L form the OH group is on the left side.
• D-glucose and L-glucose are enantiomers
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Optical Activity:
• Is the capacity of a substance to rotate the
plane of polarized light passing through a
solution, the light will either be rotated towards
right or left.
• This rotation is because of the presence of
asymmetric carbon atom.
• If it is rotated towards left (counterclockwise
direction): levorotatory or (-).
• If it is rotated towards right (clockwise
direction): dextrorotatory or (+).
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 EPIMERS:
• EPIMERS are sugars that differ in
configuration at ONLY 1 POSITION.
• Examples of epimers:
D-glucose and D-galactose (epimeric at
C4)
D-glucose and D-mannose (epimeric at
C2)
D-idose and L-glucose (epimeric at C5)
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Anomerism:
• The alpha and beta cyclic forms of D-
glucose are known as anomers. They differ
from each other in configuration only
around C1.
• The carbonyl carbon after cyclization
becomes the anomeric carbon (hemiacetal
carbon).
• This creates α and β configuration.
• In α configuration the hydroxyl group is on
the same of the ring in fischer projection. In
Haworths it is on the trans side of CH2OH. 27
Cyclization:
• Less then 1% of carbohydrates are exist
in an open chain form.
• Predominantly found in ring form.
• Involving reaction of C5 of hydroxyl group
with the C1 of aldehyde group or C2 of
keto group.
• Six membered ring structures are called
Pyranoses .
• Five membered ring structures are called
Furanoses . 28
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H

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Mutarotation:
• Is the change in the specific optical
rotation by the interconversion of
alpha and beta forms of D-glucose
to an equilibrium mixture.

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Reducing sugars:

• Sugars in which the oxygen of the

anomeric carbon is free and not
attached to any other structure, such
sugars can act as reducing agents
and are called reducing sugars.

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Glycosides:
• Glycosides are compounds containing a
carbohydrate or with a non-carbohydrate
residue in the same molecule.
• The non-carbohydrate moiety is known as
aglycane such as phenol, sterol, glycerol and
methanol.
• The glycosidic bond can be N-linked or O-
linked.
• If the carbohydrate portion is glucose, the
resulting compound is a glucoside; if
galactose, a galactoside etc. 36
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Amino sugars:
• In addition to sugars they are containing an
amino group.
• Glucosamine is a constituent of hyaluronic
acid.
• Galactosamine (chondrosamine) is a
constituent of chondroitein.
• Mannosamine is an important constituent of
mucoprotein.
• Several antibiotics contain amino sugars
(erythromycin contains a dimethylamino
sugar).
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Thanks
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