Derivatives Of Monosaccharides

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Derivatives of Monosaccharides

Monosaccharides form a variety of derivatives which are constituents of structural and storage polysaccharides.

Deoxysugars

Deoxyribose is a constituent of high molecular weight deoxyribonucleic acid chains of which genes are made. It is derived from ribose in which the hydroxyl group at C- 2 is replaced by a hydrogen atom.

Sugar Acids

Sugar acids are derived by oxidation of aldehyde group or the primary OH group or both. When the –CHO group of glucose is oxidized, gluconic acid is formed, while oxidation of the primary alcoholic group (C-6) yields glucuronic acid. Oxidation of both, the aldehyde as well as the primary alcoholic group results in the formation of glucaric acid.

Ascorbic acid (vitamin C) which is the lactone of 2-keto-L-gulonate is an important sugar acid of great biological importance. In many biological reactions ascorbic acid is a hydrogen donor and in some cases is also serves as a strong reducing agent.

sugar acids

Sugar Alcohols

Reduction of the aldehyde or ketone group of monosaccharides yields sugar alcohols.

sugar alcohols

An important cyclic form of sugar alcohol is myoinositol which is a constituent of phosphatidyl inositol.

Myoinositol

Amino Sugars

These are derived from sugars by replacement of a hydroxyl group by an amino group. Glucosamine is a derivative of glucose in which the OH group on C-2 is replaced by an amino group. Glucosamine is a component of chitin, a polysaccharide present in the outer covering of arthropods. Similarly if the OH group is replaced by N- acetylamino group, the compound is known as N – acetyl – D- glucosamine. Galactosamine is found in the cartilages and in many glycosphingolipids.

amino sugars

Sialic Acid

Sialic acid is a keto sugar consisting of nine carbon atoms and forms an important component of membrane proteins, called glycophorins. Sialic acid is also known as N- acetylneuraminic acid and when present in an oligosaccharide chain, it is always the last sugar in the chain. This is widely distributed in bacteria and animal tissues.

The cell wall of bacteria contains N- acetylmuramic acid, which is also a 9- carbon derivative. The sugar derivative has an amino group which is acylated; land consists of D – glucosamine linked to lactic acid (3 carbon compound) through an easter bond.

sialic acid

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