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Issue 39, 2014
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Exploring functional cyclophellitol analogues as human retaining beta-glucosidase inhibitors

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Abstract

The natural product, cyclophellitol and its aziridine analogue are potent mechanism-based retaining β-glucosidase inhibitors. In this paper we explore the inhibitory potency of a number of cyclophellitol analogues against the three human retaining β-glucosidases, GBA, GBA2 and GBA3. We demonstrate that N-alkyl cyclophellitol aziridine is at least equally potent in inhibiting the enzymes evaluated as its N-acyl congener, whereas the N-sulfonyl analogue is a considerably weaker inhibitor. Our results complement the literature on the inhibitory potency of cyclophellitol analogues and hold promise for the future design of more effective activity-based retaining glycosidase probes with respect to probe stability in physiological media.

Graphical abstract: Exploring functional cyclophellitol analogues as human retaining beta-glucosidase inhibitors

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Publication details

The article was received on 29 Jul 2014, accepted on 19 Aug 2014 and first published on 19 Aug 2014


Article type: Paper
DOI: 10.1039/C4OB01611D
Citation: Org. Biomol. Chem., 2014,12, 7786-7791
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    Exploring functional cyclophellitol analogues as human retaining beta-glucosidase inhibitors

    K. Li, J. Jiang, M. D. Witte, W. W. Kallemeijn, W. E. Donker-Koopman, R. G. Boot, J. M. F. G. Aerts, J. D. C. Codée, G. A. van der Marel and H. S. Overkleeft, Org. Biomol. Chem., 2014, 12, 7786
    DOI: 10.1039/C4OB01611D

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