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.
Warner
T G
TG
University of Tennessee, Memphis, Pediatrics Department 38163.
Lee
L A
LA
D000345:Affinity Labels / Q000138:chemical synthesis*; D001386:Azides / Q000138:chemical synthesis*; D002352:Carrier Proteins / Q000032:analysis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009439:Neuraminidase / Q000032:analysis*; D009904:Optical Rotation; D010777:Photochemistry; D012794:Sialic Acids / Q000032:analysis*; D013055:Spectrophotometry, Infrared; D013400:Sugar Acids / Q000138:chemical synthesis*
D000345:Affinity Labels; D001386:Azides; D002352:Carrier Proteins; D007202:Indicators and Reagents; D012794:Sialic Acids; D013400:Sugar Acids; C057028:(4-azido-2-nitrophenyl)-5-acetamido-2,3,5-trideoxy-2-thioglycerogalacto-2-nonulopyranosidonic acid; D009439:Neuraminidase