CARBOHYDRATES

What are Carbohydrates?

Polyhydroxy compounds (poly-
alcohols) that contain a carbonyl
(C=O) group.
Most have formula Cn(H2O)n, “hydrate
of carbon.”
Stoichiometric formula (CH2O)n
Nomenclature and Classification
Simple carbohydrates are termed
as sugars or saccharides.
The carbonyl group are in two
forms
a) Aldehyde form called Aldose
b) Ketone form called Ketose
Nomenclature and Classification
Nomenclature and Classification
Carbohydrates are classified according
to the number of simple sugar units
produce on hydrolysis.
1. Monosaccharides
-carbohydrates that do not
hydrolyzed into simpler carbohydrates.
Nomenclature and Classification
1. Monosaccharides
- They are classified depending upon the
number of C atoms they possess.
a) Trioses
b) Tetroses
c) Pentoses
d) Hexoses
Nomenclature and Classification
2. Disaccharides
- carbohydrates that yield two molecules
of monosaccharides upon hydrolysis.
Ex: Maltose - yields 2 molecules of
glucose
Sucrose - yields glucose and fructose
Lactose - yields galactose and glucose
Nomenclature and Classification
3. Oligosaccharides
-carbohydrates that yield from 2 to 10
molecules of monosaccharides on hydrolysis.
Ex. Maltotriose and Raffinose
4. Polysaccharides
- carbohydrates that yield more than 10
molecules of monosaccharides on hydrolysis.
Ex. Starch and Dextrins
Monosaccharides
Smallest monosaccharides are the Trioses,
(CH2O)n where n = 3.
There are two Trioses
1. Glyceraldehyde
2. Dihydroxyacetone
Trioses
CHO CHO C2 of glyceraldehyde is
H C OH HO C H
bonded to 4 different
groups.
CH2OH CH2OH
It is chiral or
D-glyceraldehyde L-glyceraldehyde assymetric carbon.
CHO CHO Every chiral C has two
enantiomers, D and L.
H C OH HO C H
Enantiomers are non
CH2OH CH2OH
superimposable mirror
D-glyceraldehyde L-glyceraldehyde images of one another.
Enantiomers (mirror images)
Fischer Projections
The most compact way to represent
enantiomers.
In Fischer Projection, C atoms are lined up
vertically, the hydroxyl group is drawn to the
right for the D-enantiomer and to left for
the L-enantiomer.
Note: The most important naturally
occurring saccharides are in the D form.
Trioses
Tetroses
Pentoses
Aldopentoses Ketopentoses
Hexoses
Aldohexose, Glucose Ketohexose, Fructose
The D Aldose Family
Epimers
- Sugars that differ only in their stereochemistry at a
single carbon.

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Ring Structures of Monosaccharides
Monosaccharides with 5 or more
Carbons can form ring structures via
internal hemiacetal linkage.
The resulting ring structures are
similar to the structures of either
pyran or furan.
Ring Structures
Pyran (Pyranose) Furan (Furanose)

O O

Carbo.ppt
Ring Structures
Glucose forms an intra-molecular
hemiacetal, as the C1 aldehyde & C5
OH react, to form a 6-member
pyranose ring.
For Fructose Cyclic hemiacetal formed
by reaction of C=O at C2 with -OH at
C5 to form a 5-member furanose ring.
Preferred Cyclic Structures
For Glucose the preferred ring
structure is the Pyranose form.
For Fructose, the preferred ring
structure is the Furanose form.
Cyclic Structure for Glucose
Pyranose Form of Glucose
CHO
H OH H OH H OH
HO HO
HO HO H HO
HO H H OH HO OH
H OH H OH
H OH H OH H H
CH2OH
alpha-(+)-glucose beta-(+)-glucose

CH2OH CH2OH
H O H O OH
H
OH H OH H
OH OH OH H
H OH H OH
Furanose Form of Fructose
Cyclic Structure for Fructose
CH2OH
O
CH2OHO CH2OH HO H CH2OHO OH
H OH H OH H OH
H OH H OH H CH2OH
OH H CH2OH OH H

alpha-D-fructofuranose D-fructose beta-D-fructofuranose

Anomers
In the resulting ring structures, C1 in
glucose becomes chiral C.
So also C2 in fructose.
C1 and C2 are known as Anomeric
Carbons.
Isomers differing in configuration only at
Anomeric Carbon are called, ANOMERS.
There are two anomers, α and β.
Anomers
Mutarotation
Is the interconversion of α- and β-
anomers.
For example, in aqueous solution,
glucose exists as a
mixture of 36% α - and 64% β - (>99%
of the pyranose
forms exist in solution).
Interconversion
Derived Monosaccharides
 Are monosaccharides which contain
functional groups other than those
normally present.
Examples are:
• Phosphate Sugars
• Acids Sugars
• Alcohol sugars
• Amino Sugars
1. Phosphates Sugars
2. Acid Sugars
Sugar acids are carboxylic acids
Produced from aldoses by:
(1) Oxidation of C-1 to yield an aldonic
acid
(2) Oxidation of the highest-numbered
carbon to an alduronic acid
Acid Sugars
COOH CHO

H C OH H C OH

HO C H HO C H

H C OH H C OH

H C OH H C OH

CH2OH COOH

D-gluconic acid D-glucuronic acid

3. Sugar Alcohols (polyhydroxy
alcohols)
4. Amino Sugars
CH2OH CH2OH

H O H H O H
H H
OH H OH H

OH OH OH O OH
H NH2 H N C CH3
H
-D-glucosamine -D-N-acetylglucosamine
Disaccharides
Produce by joining two
monosaccharides.
Linkage is possible through formation
of Glycosidic Bond.
Reaction is analogous to that of the
peptide bond where in there is also a
removal of H2O molecule.
Common Disaccharides
1. Sucrose
 Commonly called table sugar.
 Formed by linking glucose (α) &
fructose (β).
 Linkage is (12)
 The full name is -D-glucopyranosyl-
(12)-b-D-fructopyranose.)
Common Disaccharides
2. Lactose
 Known as milk sugar
 Formed by linking Galactose (β ) and
Glucose (β)
 Linkage is β (1 4).
 Its full name is b-D-galactopyranosyl-
(1 4)--D-glucopyranose
Lactose Intolerance
also called lactase deficiency or hypolactasia, is
the inability to digest and metabolize lactose.
caused by a lack of lactase, the enzyme required to
break down lactose in the digestive system.
results in symptoms including abdominal
pain, bloating, flatulence, diarrhea, nausea and aci
d reflux.
Common Disaccharides
3. Maltose
 Malt sugar.
 Formed by linking two glucose (α)
 Linkage is α (1 4)
Reducing Sugars
Sugars having free anomeric carbon.
Has a potential free aldehyde group
that could be oxidized by Fehling’s
solution. (CuSO4 in alkaline solution)
Ex. Lactose, Maltose, Gentiobiose
Polysaccharides
Perform a variety of functions
1. Storage
2. Structural
Can be
1. Homoglycans - homopolysaccharides
containing only one type of monosaccharide.
 2. Heteroglycans - heteropolysaccharides
containing residues of more than one type of
monosaccharide.
Storage Polysaccharides
1. Starch
- the storage fuel molecules in plants.
2. Glycogen
- energy storage molecules in animals.
- sometimes called as animal starch.
Both starch and glycogen are made up of
amylose and amylopectin.
Amylose
is an unbranched glucose polymer
with (14) linkages. (100-1000
residues)
The end of the polysaccharide with
an anomeric C1 not involved in a
glycosidic bond is called the
reducing end.
Amylose

O O O O O O O O

O O O O O O O O
Amylopectin
is a glucose polymer with mainly
(14) linkages, but it also has branches
formed by (16) linkages.
The branch contains 15-25 glucose
residues; some branches are themselves
branched.
Can have 300-6000 glucose units.
Amylopectin
O O O O O O

O O O O O O
CH2
O O O O O O O O

O O O O O O O O
Structural Polysaccharides
1. Cellulose
 is a polymer of glucose with a b(14)
linkages.
 most abundant organic molecule on earth.
 Synthesized by plants & some bacteria.
 found in cell walls of plants.
Cellulose
Has small difference from starch, but has
remarkable consequences.
a) can exists in a fully extended conformation
with each glucose residue flipped by 180 0.
This promotes intra-chain and inter-chain
H-bonds and van der Waals interactions,
that cause cellulose chains to be straight &
rigid, and pack with a crystalline
arrangement in thick bundles .
Cellulose
b) Animal enzymes that are able to catalyze
the cleavage of the α (14) linkage in
starch, cannot cleave cellulose.
Ruminants (animals like cows, horses,
goats, sheep) can digest cellulose because
their digestive tracts contain symbiotic
bacteria that produce the necessary
cellulase.
Structure of cellulose
CH2OH 6CH OH CH2OH CH2OH CH2OH
2
O 5 O O H O H O OH
H H H
H H H H H
OH H 1 O 4 OH H 1 O OH H O OH H O OH H
OH H H H
H 2 H
3
H OH H OH H OH H OH H OH
cellulose
O O

O O

O O

O O

O O

O O

O O

O O
Structural Polysaccharides
2. Chitin

Major structural material in exoskeleton

of arthropods (insects, spiders, etc.) and
mollusks (Clams, snails, octopus, squid)
Polymer of N-acetylglucosamine.
Has a similar structure to cellulose, except
that the OH on C2 is replaced by an
acetylated amino group.
Structure of Chitin

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Structural Polysaccharides
3. Glycosaminoglycans
(Mucopolysaccharides)
 major goup of structural materials in
vertebrate animals.
Linear polymers consist of repeating
disaccharide units composed of an N-
acetylated or N-sulfated hexosamine and
either a uronic acid (glucuronic acid or
iduronic acid) or galactose.
Glycosaminoglycans
Major function is the formation of matrix to
hold together the protein components of
skin and connective tissue.
Examples are:
a) Chondroitin sulfates
b) Keratan sulfates
c) Dermatan sulfates
d) Hyaluronic acid
Chondroitin Sulfates
Keratan Sulfates
Dermatan Sulfates
Hyaluronates/Hyaluronic acids
“ END OF PART
ONE ”
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