An azidoaryl thioglycoside of sialic acid. A potential photoaffinity probe of sialidases and sialic acid-binding proteins.

An azidoaryl thioglycoside of sialic acid was prepared, as a potential photoaffinity probe reagent for the analysis of sialidases and sialic acid-binding proteins, by treatment of the glycosyl chloride of N-acetylneuraminic acid methyl ester with potassium thioacetate to give, in 70% yield, methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-S-acetyl-2,3,5-trideoxy-2-thio-alph a-D- glycero-D-galacto-2-nonulopyranosonate. Selective hydrolysis of the thioacetate ester, followed by condensation with 4-fluoro-3-nitrophenyl azide, O-deacetylation, and hydrolysis gave (4-azido-2-nitrophenyl)- 5-acetamido-2,3,5-trideoxy-2-thio-alpha-D-glycero-D-galacto-2- nonulopyranosidonic acid.