beta-D-Galactopyranosyl-thiohydroximates and D-galactopyranosylidene-spiro-oxathiazoles: synthesis and enzymatic evaluation against E-coli galactosidase

摘要

By reaction with arylhydroximoyl chlorides, 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-galactopyranose was converted to the corresponding beta-D-galactopyranosyl-thiohydroximates, which gave predominantly (1S)-D-galactopyranosylidene-spiro-oxathiazoles on illumination in the presence of NBS. Conventional O-deacetylation of both thiohydroximates and oxathiazoles gave weak inhibitors of E. coli D-galactosidase (K-i 1.1-11.1 mM). (c) 2005 Elsevier Ltd. All rights reserved.