Organic Chemistry: Concepts and Applications - Headley Allan D. 2020

Synthetic Polymers and Biopolymers
20.17 N-Glycosides and Amino Sugars

In a comparable reaction to the glycoside formation described in the previous section, amines can react with monosaccharides to form N-glycoside bonds as shown in Reaction (20-74).

(20-74)ααβImage

The products of these reactions are very important in biology in that they serve as building blocks for RNA and DNA, examples of these molecules are shown below.

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By changing the amine bases bonded through the N-glycoside bond, the different bases of DNA are formed and they are shown below.

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Replacing one of the hydroxyl groups of a monosaccharide with an anime results in a new type of molecule. For example, the substitution of the OH group on the α-carbon of D-glucose results in glucosamine. Glucosamine is used to stimulate the formation and repair of cartilage found naturally in the body that cushions joint, its structure is shown below.

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