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BETA-GLUCOSIDASE INHIBITORS INCORPORATING PYRIDINIUM AS A GLUCOSYL MIMIC

TitleBETA-GLUCOSIDASE INHIBITORS INCORPORATING PYRIDINIUM AS A GLUCOSYL MIMIC
Publication TypeJournal Article
Year of Publication1995
AuthorsKnapp, S, DONG, YH, RUPITZ, K, Withers, SG
JournalBIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume5
Pagination763-766
Date PublishedAPR 6
ISSN0960-894X
Abstract

The synthesis of several 2-pyridylthio-based pseudo-disaccharides (5 - 9) is described. One of them, them, 5a, shows inhibition of Agrobacterium beta-glucosidase (K-i = 800 mu M), possibly because in protonated form it mimics the protonated substrate (or transition state, compare I) lending to the glucopyranosyl cation.

DOI10.1016/0960-894X(95)00111-6