beta-D-Galactopyranosyl-thiohydroximates and D-galactopyranosylidene-spiro-oxathiazoles: synthesis and enzymatic evaluation against E. colid-galactosidase.
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. colid-galactosidase (Ki 1.1-11.1 mM).
Elek
Rita
R
Department of Biochemistry, University of Debrecen, PO Box 50, H-4010 Debrecen, Hungary.
Kiss
László
L
Praly
Jean-Pierre
JP
Somsák
László
L
D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D004926:Escherichia coli / Q000201:enzymology; D005690:Galactose / Q000737:chemistry*; D010091:Oximes / Q000737:chemistry*; D013844:Thiazoles / Q000737:chemistry*; D001616:beta-Galactosidase / Q000037:antagonists & inhibitors*
D004791:Enzyme Inhibitors; D010091:Oximes; D013844:Thiazoles; D001616:beta-Galactosidase; D005690:Galactose