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

doi:10.1039/b709681j

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

School of Molecular Sciences

Research output: Contribution to journal › Article › peer-review

34 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 language	English
Pages (from-to)	3013-3019
Journal	Organic & Biomolecular Chemistry
Volume	5
DOIs	https://doi.org/10.1039/b709681j
Publication status	Published - 2007

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

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T1 - A 1-acetamido derivative of 6-epi-valienamine: an inhibitor of a diverse group of β-N-acetylglucosaminidases

AU - Scaffidi, Adrian

AU - Stubbs, Keith

AU - Dennis, R.J.

AU - Taylor, E.J.

AU - Davies, G.J.

AU - Vocadlo, D.J.

AU - Stick, Robert

PY - 2007

Y1 - 2007

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AB - 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.

U2 - 10.1039/b709681j

DO - 10.1039/b709681j

M3 - Article

C2 - 17728868

SN - 1477-0520

VL - 5

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EP - 3019

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

ER -

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

Abstract

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