Issue 18, 2007
From the journal:

Organic & Biomolecular Chemistry

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

Adrian Scaffidi,a   Keith A. Stubbs,*b   Rebecca J. Dennis,c   Edward J. Taylor,c   Gideon J. Davies,c   David J. Vocadlob  and  Robert V. Sticka  

* Corresponding authors

a Chemistry M313, School of Biomedical, Biomolecular and Chemical Sciences, The University of Western Australia, 35 Stirling Hwy, Crawley, WA, Australia
Fax: +61 8 6488 1005
Tel: +61 8 6488 320

b Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, BC, Canada
E-mail: kstubbs@sfu.ca
Tel: +1 604-291-3530

c York Structural Biology Laboratory, Department of Chemistry, The University of York, Heslington, York, United Kingdom

Abstract

The synthesis of an analogue of 6-epi-valienamine bearing an acetamido group and its characterisation as an inhibitor of β-N-acetylglucosaminidases are described. The compound is a good inhibitor of both human O-GlcNAcase and human β-hexosaminidase, as well as two bacterial β-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.

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

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Article information

DOI
https://doi.org/10.1039/B709681J
Article type
Paper
Submitted
27 Jun 2007
Accepted
16 Jul 2007
First published
15 Aug 2007

Org. Biomol. Chem., 2007,5, 3013-3019

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

A. Scaffidi, K. A. Stubbs, R. J. Dennis, E. J. Taylor, G. J. Davies, D. J. Vocadlo and R. V. Stick, Org. Biomol. Chem., 2007, 5, 3013 DOI: 10.1039/B709681J

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