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

Adrian Scaffidi, Keith Stubbs, R.J. Dennis, E.J. Taylor, G.J. Davies, D.J. Vocadlo, Robert Stick

Research output: Contribution to journalArticle

32 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)3013-3019
JournalOrganic & Biomolecular Chemistry
Volume5
DOIs
Publication statusPublished - 2007

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