Carbohydrates chemistry

Dr MUHAMMAD WASEEM KAUSAR

Assistant professor. Bio-chemistry
I M D C.
 Carbohydrate
– Cell structure:
s
– Cellulose, LPS, chitin

Chitin in
exoskeleton

Cellulose in plant cell walls Lipopolysaccharides (LPS)

in bacterial cell wall
The elements which make up
carbohydrates are:

•Carbon (C)
•Hydrogen (H)
•Oxygen (O)
Some carbohydrates also contain N and S
 Carbohydrates
• commonly known as sugars, Saccharide, hydrates (H2o) of
carbon
• ARE ALDEHYDE OR KETONE DERIVATIVES OF POLYHYDRIC
ALCOHOLS or
• Are polyhydroxylated compounds with at least 3 carbons, with potentially
active carbonyl group, which may be either aldehyde(CHO) or ketone
(CO) group.
• general formula CnH2n On .but
Many CHO contain H & O not in the same proportion
As in water .e.g deoxyriboseC5H10 O4.

• Sources
– Plants
– animals
•
BIOMEDICAL
A variety of functions in the cell
IMPORTANCE
– Provides majority of energy(4.1 kilocalories/gm)
– Structural component of cell wall.
– In animal cells carbohydrates on the exterior surface of the cell serve a
recognition and identification function
– Serve as metabolic intermediate(G-6-p)
– Component of nucleotides that form DNA , RNA
– precursor for synthesis of all the other carbohydrates in the body e.g.
glycogen, galactose, ribose, glycolipids, glycoproteins and proteoglycans.
– For synthesis of FA, cholesterol, amino acids
– Carbohydrates derivatives are used as drugs e.g.
– Principal sugar in milk, galactose
– Strong detoxification agent in body e.g. Glucoronic acid
– Play a role in lubrication, cellular intercommunication, and immunity.
– Diseases ssociated with carbohydrate metabolism include Diabetes mellitus,
galactosemia, glycogen storage diseases, and lactose intolerance.
Carbohydrates Classification
no satisfactory classification.
•GENERALLY
1.Simple carbohydrates
2.Complex carbohydrates
• On the basis of hydrolysis
1.Monosaccharides
2.Disaccharides
3.Oligosaccharides,
4.Polysaccharides.
and .Derived carbohydrates
Monosaccharides
 Monosaccharides
-Single Sugar-

•Glucose

The Formula for glucose is

C6 H12 O6
 Glucose
H
C O
H C OH
HO C H
H C OH
H C OH
CH2OH

D-Glucose
9
 Fructose
CH2OH
C O
HO C H
H C OH
H C OH
CH2OH

D-Fructose 10
• These are the basic building blocks of other
carbohydrates
• Simple sugars
• Can not be further hydrolyzed
• Name usually suffix - ose
• Empirical formula is CnH2n On, here “ n” =3 or more
• Color less, white, solid crystalline in nature, soluble
in water, sweet taste, insoluble in non-polor solvent
• Simplest m/s are two, which are 3 carbon. Trioses
glyceraldehyde & dihydroxyacetone.
• Subdivision of m/s
1.On the basis of “C” atoms.
2.On the basis of functional group.
Classification of m/s
1.number of carbons
2.On the basis of functional group
• Aldoses are monosacchrides with an aldehyde
group and many hydroxyl (-OH) groups.

• Ketoses are monosacchrides with a ketone

group and many hydroxyl (-OH) groups.

14
Some properties of m/s with reference to
glucose
 :
chiral Carbon

ISOMERS=
2n.
 Chirality rules.

1. Monosaccharides contain one or more asymmetric C-

atoms: get D- and L-forms, where D- and L- designate
absolute configuration
2. D-form: -OH group is attached to the right of the
asymmetric carbon
3. L-form: -OH group is attached to the left of the
asymmetric carbon
4. If there is more than one chiral C-atom: absolute
configuration of chiral C furthest away from carbonyl
group determines whether D- or L-
 Ring formation / Ring structure

An aldose: Glucose
A ketose: Fructose
 Ring Structure
• Linear known as “Fischer” structure”
• Ring know as a “Haworth projection”
• Cyclization via intramolecular hemiacetal (hemiketal)
formation
• C-1 becomes chiral upon cyclization - anomeric carbon
• Anomeric C contains -OH group which may be α or β
(mutarotation α ⇔ β )
 EPIMERS
•Carbohydrate isomers that differ
in configuration around only one
specific carbon atom (with the
exception of the carbonyl carbon)
Epimers: Isomers differing as a
result of variations in
configuration of the -OH and -H
on carbon
atoms 2, 3, and 4 of glucose are
known as epimers. . For example,
glucose and galactose are C-4
epimers ,their structures differ
only in the position of the -OH
group at carbon 4
 OPTICAL ACTIVITY
• The presence of asymmetric carbon atoms also
confers optical activity on the compound. When
a beam of plane-polarized light is passed through
a solution of an optical isomer, it will be rotated
either to the right, dextrorotatory (+); or to the
left, levorotatory (−). The direction of rotation is
independent of the stereochemistry of the sugar,
so it may be designated D(−), D(+), L(−), or L(+).
For example, the naturally occurring formof
fructose is the D(−) isomer.