Carbohydrate Chemistry: Dr. Herat D. Soni Assistant Professor Rural Medical College Loni
Carbohydrate Chemistry: Dr. Herat D. Soni Assistant Professor Rural Medical College Loni
Carbohydrate Chemistry: Dr. Herat D. Soni Assistant Professor Rural Medical College Loni
Definition
Carbohydrates
may be defined as
polyhydroxy aldehydes or
ketones or compounds which
produce them on hydrolysis.
Formula = (C.H2O)n
Biomedical Importance
Sources
CLASSIFICATION OF
CARBOHYDRATE
Classification
1
Monosaccharide
Oligosaccharide
Polysaccharide
Monosaccharide
Cannot further Hydrolyzed
Oligosaccharide
Polysaccharides
Polysaccharides
Homopolysaccharides
Starch
Glycogen
Cellulose
Inulin
Dextrans
Chitin
Heteropolysacchrides
Agar
Mucopolysaccharide
Isomers
Same chemical formula but different
structural formula
Example = Glucose and fructose
C6H12O6
Stereoisomer
D and L isomerism(Enantiomers)
Epimers
Epimers
Anomers
To understand this we first understand
Three Representations of Glucose
Structure
open chain
projection
formula
Fischer's
formula
Haworths
formula
Fischer's formula
Haworth formula
Mutarotation
When
D glucose is crystallized at
room temperature, and a fresh
solution is prepared, its specific
rotation of polarized light is +112o;
but after 1218 hours it changes
o
to +52.5 .
This
Mutarotation
-D-glucopyranose
O
Rotation of 112
-D-glucopyranose
0
Rotation of 19
DISACCHARIDES
Sucrose
Maltose
Isomaltose
Lactose.
Sucrose
Lactose
Lactose intolerance
Maltose
Isomaltose
REACTIONS OF
CARBOHYDRATE
Benedicts test
Principle
The principle of Benedict's test is that
when reducing sugars are heated in the
presence of an alkali(pH 10.6), they get
converted to powerful reducing
compounds known as enediols.
Enediols reduce the cupric ions (Cu2+)
present in the Benedict's reagent to
cuprous ions (Cu+) which get precipitated
as insoluble red copper oxide.
Non-Carbohydrates giving
positive Benedict s test
High concentration of Uric acid and
Ketones
Homogentisic acid (solution turns black
due to black colored oxidized
homogentisic acid)
Vitamin C (even without Boiling)
Certain drugs like aspirin, cephalosporins
Glucose + O2
Glucose Oxidase
Gluconolactone + H2O2
H2O2 + (reduced colourless dye)
Peroxidase
(Oxidized colored dye)
Thus,
Osazone Formation
All
Molischs test
All carbohydrates when treated with conc.
sulphuric acid undergo dehydration to
give fufural compounds. These
compounds condense with Alpha-napthol
to form colored compounds.
Molish test is given by sugars with at
least five carbons because it involves
furfural derivatives, which are five carbon
compounds.
Fehlings test
Same
Barfoeds test
This test is based on the same principle as
Benedicts test.
But, the test medium is acidic.
In acidic medium (pH 4.6)
monosaccharides react faster than
disaccharide.
Barfoeds reagent contains copper acetate
in glacial acetic acid.
Seliwanoffs test
Seliwanoffs
Cherry
red color
Oxidation
Significance of reduction
Sorbitol,
Cataract
Retinopathy
Nephropathy
Neuropathy
Lactulose
Glycosides
Biomedical importance of
glycosides
Streptomycin
Antibiotic
Given in Tuberculosis
Phloridzin
cause renal damage, glycosuria.
Blocks the transport of sugar across the
mucosal cells of small intestine & also
renal tubular epithelium.
Formation of Esters
Esterification
of alcoholic groups of
monosaccharides with phosphoric
acid is a common reaction in
metabolism.
Examples :Glucose-6-phosphate, and
Glucose-1-phosphate.
ATP donates the phosphate moiety.
Amino sugars
Importance
Amino sugars
Found in
Glucosamine
Galactosamine
Chondroitin sulphate of
cartilage, bone and tendons.
Mannosamine
constituent of glycoproteins
N-acetylglucosamine
(GluNac) and Nacetyl galactosamine
(GalNac)
constituents of
glycoproteins,
Mucopolysaccharide and cell
membrane antigens.
Deoxy Sugars
Oxygen of the hydroxyl group may be removed to
form Deoxy sugars
Homopolysaccharides
Starch
Glycogen
Cellulose
Inulin
Dextrans
Chitin
Starch
It
Amylose
Starch
Hydrolysis of starch
Amylodextrin
Short
time to
long time
Glycogen
Cellulose
It is made up of glucose units combined
with beta-1,4 linkages.
It has a straight line structure, with no
branching points.
Beta-1,4 bridges are hydrolyzed by the
enzyme cellobiase. But this enzyme is
absent in animal and human digestive
system, and hence cellulose cannot be
digested.
Importance
It is a major constituent of fiber, the
nondigestable carbohydrate.
Fiber can absorb 1015 times its own
weight in water, drawing fluid into
the lumen of the intestine
Increasing bowel motility
1.Decrease the risk for constipation
Intestine
Bile salt
Decreases
serum
cholesterol
level
Fibers
Excreted
Inulin
It is a long chain homoglycan composed
of D-fructose units with repeating beta-1,2
linkages.
It is the reserve carbohydrate present in
various bulbs and tubers, such as onion,
garlic.
It is clinically used to find renal
clearance value and glomerular
filtration rate.
Dextrans
These are highly branched homopolymers
of glucose units with 1-6, 1-4 and 1-3
linkages. They are produced by microorganisms.
Since they will not easily go out of
vascular compartment, they are used for
intravenous infusion as plasma volume
expander for treatment of hypovolemic
shock.
Chitin
It
is present in exoskeletons of
insects.
It is composed of units of Nacetylglucosamine with beta-1,4
glycosidic linkages.
Heteropolysaccharides
Agar
Mucopolysaccharide
Agar
Agar = The linear polysaccharide Agarose
+ agaropectin
It is dissolved in water at 100C, which
upon cooling sets into a gel. Agarose is
used as matrix for electrophoresis.
Agar cannot be digested by bacteria and
hence used widely as a supporting agent to
culture bacterial colonies.
Mucopolysaccharide
i.e. glycosaminoglycans(GAGs)
GAGs
Composition
Hyaluronic
acid
D-glucuronic acid
and N-acetyl Dglucosamine
Connective tissue
Synovial fluid
Vitreous humor
Gel around ovum
bone, cartilage,
Tendons,heart
valves and skin.
Helps to maintain
the structure And
shapes of tissues
Helps to maintain
shapes of tissues
Keratan
sulphate
cornea
tendons
Keeps cornea
Transparent
Heparin
sulphated glucosamine
and glucuronic acid or
iduronic acid
Anticoagulant
Clearing factor
Hyaluronic acid
Hyaluronidase
Breaks b(1-4 linkages) in hyaluronic acid.
Present in high concentration in testes,
seminal fluid, and in certain snake and insect
venoms.
Hyaluronidase of semen clears the gel
(hyaluronic acid) around the ovum allowing a
better penetration of sperm into the ovum.
Serves important role in fertilization
Hyaluronidase of bacteria helps their invasion
into the animal tissues.
Chondroitin sulphate
Dermatan sulfate
Keratan sulphate
Heparin
Capillary
Lipoprotein
lipase
EN
HS
Heparin displaces
lipoprotein lipase from
heparan sulphate binding
site hence clearing factor
Heparan
sulphate
On capillary
endothelial
wall surface
Proteoglycans and
Glycoproteins
Proteoglycans
Glycoprotein
Glycophorin
Collagen
Ceruloplasmin
Immunoglobulin
Intrinsic factor
Fibrinogen
Major function
glycoprotein of
erythrocytes cell
membrane
Structure of cartilage
and bone
Transport protein
Defense against
infection
Absorption of vitamin
B12
Blood clotting
Thank
you
Any questions?