Carbohydrates

chemistry
Dr. Mohammad Waseem Kausar
Assistant professor, Biochemistry
IMDC
SOME PROPERTIES OF
MONOSECCHARIDES
 1. formation of polyols or
alcohol
when carbonyl gp is reduced to a

hydroxyl gp
Keto sugar of more then 3 c can

yeild more then one sugar

alcohal because of creation of
new asym- center at c2. e.g
fructose yeild a mixture of
sorbitol & mannitol.
Glyceradehyde & DHA = glycerol
Mannose = mannitol

 sorbitol (DM)
Sugar alcohol though derived from
reducing m/s are not reducing agents,
exist only in straight chain form.
Uses of sugar alcohol → prevention of

dental caries,

mannitol
 2,Oxidation to form Sugar
Acids
glucose
D-Glucuronic acid

When a carbonyl gp or a –OH gp is oxidized t o –COOH gp

oxidized aldoses m ay form
1. m onobasic Aldonic acids (gluconic acids) = oxidat ion at C1
2. m onobasic Uronic acids(glucoronic acids) = oxidat ion at C 6
3. dibasic saccharic acid (glucaric acids) = oxidat ion at bot h C1 &
C6
Glucuronic acid= sm all am ount s from t he diet ., int racellular lysosom al
degradat ion of glycosam inoglycans, via t he uronic acid pat hway. The
endproduct of glucuronic acid is D-xylulose 5-phosphat e, which can ent er
t he hexose m onophosphat e pat hw ay and produce t he glycolyt ic
int erm ediat es glyceraldehyde 3-phosphat e and fruct ose 6-phosphat e .
The act ive form of glucuronic acid t hat donat es t he sugar in
glycosam inoglycan synt hesis and ot her glucuronylat ing react ions is UDP-
glucuronic acid, w hich is produced by oxidat ion of UDP-glucose
3,Crystal
formation(osazone)
 They have a characteristic melting points,
 Structure and precipitation time.
 Valuable in identification of
sugars(diagnostic value)
 Reaction take place only the carbonyl C &
next adjacent C.
 Glucose, mannose and fructose due to
simmilar in structure form the same
osazone. But galactose differs at C4.
Amonia + analine + H2O
 Reducing sugars

 Ifthe oxygen on the anomeric

carbon of a sugar is not attached to
any other structure, that sugar can
act as a reducing agent and is
termed a reducing sugar. Such
sugars can react with chromogenic
agents.
 the anomeric carbon of the sugar
becoming oxidized.
 the other hydroxyl groups on the
molecule are not involved.

Amino Sugar formation

eit her D-glucosam ine or D-

galact osam ine,
t he am ino group is usually
acet ylat ed, t hus elim inat ing it s
posit ive charge.
The am ino sugar m ay also be
sulfat ed on carbon 4 or 6 or on a
nonacet ylat ed nit rogen.
Deoxy sugars
 Lack of an oxygen
 Posses a hydrogen atom
in place of –OH.
 It does not form
osazones
 L-fucose found in
glycoproteins, blood
groups.
Glycosides
 widely distributed in nature
-OH group of the anomeric carbon of a m/s,

or m/s residue, and a second compound

that may or may not be another
monosaccharide.
 Glycosidic bond, O & N linkages
aglycon = methanol, glycerol, a sterol, a

phenol, or a base such as adenine

If the second group is a hydroxyl, the O-

glycosidic bond is an acetal link because

it results from a reaction between a
hemiacetal group (formed from an
aldehyde and an OH group) and an-other
OH group.
If the second group is an amine, an N-

glycosidic bond is formed, eg, between

adenine and ribose in nucleotides such as
ATP.
 galactose, a galactoside.
glycosides therapeutically used.