Scaffidi, Adrian, Stubbs, Keith A., Dennis, Rebecca J. et al, Taylor, Edward J., Davies, Gideon J., Vocadlo, David J. and Stick, Robert V.
(2007)
A 1-acetamido derivative of 6-epi-valienamine: an inhibitor of a diverse group of β-N-acetylglucosaminidases.
Organic & Biomolecular Chemistry, 5
(18).
pp. 3013-3019.
ISSN 1477-0520
Full content URL: http://dx.doi.org/10.1039/B709681J
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| Item Type: | Article |
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| Item Status: | Live Archive |
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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.
| Additional Information: | 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. |
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| Keywords: | β-N-acetylglucosaminidases, 6-epi-valienamine |
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| Subjects: | C Biological Sciences > C700 Molecular Biology, Biophysics and Biochemistry |
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| Divisions: | College of Science > School of Life Sciences |
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| ID Code: | 6158 |
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| Deposited On: | 18 Sep 2012 15:31 |
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