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Synthesis of photoaffinity labeling derivatives of d-glucose and d-galactose

✍ Scribed by Syeda N. Husain; Bernard Gentile; Ronald R. Sauers; Alexander Eichholz

Publisher
Elsevier Science
Year
1983
Tongue
English
Weight
479 KB
Volume
118
Category
Article
ISSN
0008-6215

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✦ Synopsis

Two new photoaffinity reagents having photoreactive groups attached to C-6 of D-galactose have been prepared. 6-N-(6Azido-2-hydroxybenzoyl)-D-glucopyranosylamine and 6-N-(4-azido-2-hydroxybenzoyl)-D-galactopyranosylamine were synthesized by acylation of the protected amino sugars with 4-azidosalicoyl chloride or by treating the amine with 4-azidosalicylic acid. Subsequent iodination of the aromatic ring yields the diiodo derivative. Deprotection yields the sugar derivatized at C-6 by the diiodinated photoaffinity reagent. Photoaffinity reagents having high specific activity may be prepared by this procedure.

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