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Issue 84, 2012
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Tuning the leaving group in 2-deoxy-2-fluoroglucoside results in improved activity-based retaining β-glucosidase probes

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Abstract

The potency of 2-deoxy-2-fluoroglycosides in activity-based profiling of human acid β-glucosidase is drastically improved by introducing an N-phenyl trifluoroacetimidate leaving group at the anomeric center. Protonation by the general acid–base catalyst in the active site turned out to be a prerequisite, making the imidate probe a genuine mechanism-based glycosidase inactivator.

Graphical abstract: Tuning the leaving group in 2-deoxy-2-fluoroglucoside results in improved activity-based retaining β-glucosidase probes

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Supplementary files

Article information


Submitted
03 Aug 2012
Accepted
16 Aug 2012
First published
20 Aug 2012

Chem. Commun., 2012,48, 10386-10388
Article type
Communication

Tuning the leaving group in 2-deoxy-2-fluoroglucoside results in improved activity-based retaining β-glucosidase probes

M. T. C. Walvoort, W. W. Kallemeijn, L. I. Willems, M. D. Witte, J. M. F. G. Aerts, G. A. V. D. Marel, J. D. C. Codée and H. S. Overkleeft, Chem. Commun., 2012, 48, 10386
DOI: 10.1039/C2CC35653H

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