A 1-acetamido derivative of 6-epi-valienamine: an inhibitor of a diverse group of beta-N-acetylglucosaminidases

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Research output: Contribution to journal › Article

Published copy (DOI)

10.1039/b709681j

Author(s)

Adrian Scaffidi
Keith A. Stubbs
Rebecca J. Dennis
Edward J. Taylor
Gideon J. Davies
David J. Vocadlo
Robert V. Stick

Department/unit(s)

Chemistry

Publication details

Journal	Organic and Biomolecular Chemistry
Date	Published - 2007
Issue number	18
Volume	5
Number of pages	7
Pages (from-to)	3013-3019
Original language	English

Abstract

The synthesis of an analogue of 6-epi-valienamine bearing an acetamido group and its characterisation as an inhibitor of beta-N-acetylglucosaminidases are described. The compound is a good inhibitor of both human O-GlcNAcase and human beta-hexosaminidase, as well as two bacterial beta-N-acetylglucosaminidases. A 3-D structure of the complex of Bacteroides thetaiotaomicron BtGH84 with the inhibitor shows the unsaturated ring is surprisingly distorted away from its favoured solution phase conformation and reveals potential for improved inhibitor potency.

Research areas

SUBSTRATE-ASSISTED CATALYSIS, O-GLCNACASE, D-GLUCOSAMINIDASE, GLYCOSIDE HYDROLASE, MECHANISM, HEXOSAMINIDASE, GLUCOSIDASE, ANALOGS, CRYSTALLOGRAPHY, PURIFICATION

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