160707-24-4Relevant academic research and scientific papers
SYNTHESIS, STRUCTURE AND ENZYMATIC EVALUATION OF NEW SPIRO OXATHIAZOLE SUGAR DERIVATIVES
Praly, Jean-Pierre,Faure, Rene,Joseph, Benoit,Kiss, Laszlo,Rollin, Patrick
, p. 6559 - 6568 (1994)
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.
β-D-Galactopyranosyl-thiohydroximates and D-galactopyranosylidene- spiro-oxathiazoles: Synthesis and enzymatic evaluation against E. coli D-galactosidase
Elek, Rita,Kiss, Laszlo,Praly, Jean-Pierre,Somsak, Laszlo
, p. 1397 - 1402 (2007/10/03)
By reaction with arylhydroximoyl chlorides, 2,3,4,6-tetra-O-acetyl-1-thio- β-d-galactopyranose was converted to the corresponding β-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 (Ki 1.1-11.1 mM).
