M. L. Chawla, O. P. Bahl
1974
Citations
0
Influential Citations
19
Citations
Journal
Carbohydrate Research
Abstract
Abstract Syntheses of p-aminophenyl 1-thio-α- L - and β- L -fucopyranosides are described. 1,2,3,4-Tetra-O-acetyl-α- L -fucopyranose, on heating with p-nitrothiophenol in the presence of p-toluenesulfonic acid under diminished pressure, gave a mixture of p-nitrophenyl 2,3,4-tri-O-acetyl-1-thio-α- and β- L -fucopyranosides, which was separated by chromatography on silica gel. When the reaction was carried out in the presence of zinc chloride at atmospheric pressure, the β-anomer was the exclusive product. Deacetylation of the aryl α- L - and α- L -thiofucopyranosides with sodium methoxide, followed by catalytic hydrogenation in the presence of palladium on barium sulfate, afforded the respective aminophenyl 1-thiofucopyranosides. The aryl thiofucopyranosides thus synthesized were tested for their inhibitory activity toward clam α- L -fucosidase. The p-aminophenyl 1-thio α- L -fucopyranoside showed a competitive-type inhibition, with a Ki of 0.71m M .