CARBOHYDRATE CHEMISTRY

 Carbohydrates (or sugars in layman terms) are organic molecules with a general
formula Cn(H2O)n. The value of n may vary between 3 to 9. They can be polyhydroxy
aldehydes CH=O or polyhydroxy ketones C=O which will form the functional group.
 Carbohydrate compounds are the most important source of energy for the activities of the
cell and other body functions. Metabolism of the dietary carbohydrates in the body provides
this energy.
 Dietary carbohydrates are subdivided into monosaccharides, the simplest sugars (glucose,
fructose, galactose, ribose), disaccharides (lactose, maltose and
sucrose), oligosaccharides (3-10 monosaccharides covalently linked to proteins or lipids,
giving rise to glycoproteins and glycolipids respectively), and lastly polysaccharides consisting
of more than 10 monosaccharides (starch, glycogen and cellulose).
 Polysaccharides can be homopolysaccharides if they are made up of the same repeating
monosaccharide units or heteropolysaccharides if they contain different monosaccharide
units eg heparin, dextran
 The carbon atoms from the sugar can also be used to synthesize new compounds
 All dietary carbohydrates will ultimately be broken down into monosaccharides, usually
glucose before being absorbed into the bloodstream
 The number of carbon atoms in the sugar can be inferred from the initial part of the name
with suffix ose - thus triose (three carbon atoms), tetrose, pentose and hexose sugars

Types of carbohydrate isomers

Carbohydrate isomers have the same molecular formula but may differ in other properties. The
various isomers are
1. Structural isomers - differing in structure eg glucose, fructose and galactose
2. Stereoisomers - having different spatial configuration. These include epimers (different orientation
of OH and H around one carbon), enantiomers (sugars that are mirror images of each other eg D and
L forms) and anomers (differ in orientation of H and OH around anomeric carbon eg alpha -glucose
and beta - glucose)
3. Optical isomers - differ in optical rotation eg dextro and levo rotatory forms

Modified Sugars
Modified sugars are obtained when the hydroxyl group gets reduced or the alcohol group is oxidised
or these are replaced by amino group
1. OH group is reduced to H - eg Deoxyribonucleic acid (DNA)
2. Amino sugar - eg glucosamine, galactosamine - OH group is replaced by amino group
3. Alcohol group of first carbon is oxidised to COOH - eg gluconic acid
4. Acidic sugar - Last carbon of glucose is oxidised to COOH - eg glucuronic acid
5. Aldehyde group is reduced to alcohol - eg glycerol, mannitol, sorbitol
Read about mannitol and sorbitol

Glycoproteins, glycolipids, glycosaminoglycans, and proteoglycans are composed of unmodified and

modified sugars
Some important glycoproteins and their functions
As mentioned previously, glycoproteins are sugar molecules covalently linked to proteins. Some of
the medically important glycoproteins are
1. Collagen - structural glycoprotein and an important component of connective tissue
2. Hormones - Thyroid stimulating hormone (TSH)
3. Prothrombin - clotting factor in blood
4. Transferrin and ceruloplasmin - transport proteins involved in transport of other molecules
5. Mucin - protective function and lubricant in lining of hollow organs
6. Immunoglobulins - important in immune function
7. Blood group antigens - important in blood grouping and blood banking
8. Glycophorin - membrane glycoprotein of red cells

Glycosaminoglycans (GAGS)
These are long, linear polysaccharides made up of repeating units of a specific disaccharide. The
disaccharide units have one acetylated amino sugar and one uronic acid (see above)—an
acidic sugar such as D-glucuronic acid or D-iduronic acid.
Glycosaminoglycans form important constituents of connective tissue (e.g., cartilage) and synovial
fluid (i.e., joint lubricant).
The six physiologically important glycosaminoglycans include heparin, heparan sulfate, dermatan
sulfate, keratan sulfate (which does not contain an acid sugar), chondroitin sulfate, and hyaluronic
acid.

Functions of GAGS
Hyaluronic acid - polysaccharide consisting of alternating D-glucuronic acid and D-N-
acetylglucosamine molecules - joint lubricant and important component of extracellular fluid
Heparin - strongly negative GAG and an important anticoagulant
Heparan sulphate - Occurs in glomerular basement membrane and thus involved in kidney filtration
function
Dermatan sulphate - important component of skin, blood vessels and heart valves
Keratan sulphate - occurs in bone, cartilage and cornea
Chondroitin sulphate - occurs in cartilage (loss of chondroitin sulphate may result in joint
degeneration and osteoarthritis).

Defective metabolism of GAGS results in a condition termed as mucopolysaccharidoses. Examples

include Hunter's syndrome and Hurler's syndrome and both are characterized by significant
accumulation of heparan sulphate and dermatan sulphate.

With this brief overview on chemistry of carbohydrates, I hope it will be easier to understand
carbohydrate metabolism

Lakshmi Venkataraman
drexampill@gmail.com
exampill.blogspot.com