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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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Publication details

The article was received on 03 Aug 2012, accepted on 16 Aug 2012 and first published on 20 Aug 2012


Article type: Communication
DOI: 10.1039/C2CC35653H
Chem. Commun., 2012,48, 10386-10388

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    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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