SYNTHESIS, STRUCTURE AND ENZYMATIC EVALUATION OF NEW SPIRO OXATHIAZOLE SUGAR DERIVATIVES

Article abstract of DOI:10.1016/S0040-4020(01)89686-1

On treatment with N-bromosuccinimide under irradiation in refluxing carbon tetrachloride, 2,3,4,6-tetra-O-acetyl-1-S-(Z)-benzhydroximoyl-1-thio-D-glucopyranose 1 and various analogs yielded new spiro anomeric oxathiazole derivatives in ca. 60percent total yield.After deacetylation, the tested major 1(S) epimers were found good competitive inhibitors of emulsin β-D-glucosidase whereas a 1(R) counterpart had no effect on the enzyme.