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

Marthe T C Walvoort, Wouter W. Kallemeijn, Lianne I. Willems, Martin D. Witte, Johannes M F G Aerts, Gijsbert A. Van Der Marel, Jeroen D C Codée, Herman S. Overkleeft

Research output: Contribution to journalArticlepeer-review


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.

Original languageEnglish
Pages (from-to)10386-10388
Number of pages3
JournalChemical Communications
Issue number84
Publication statusPublished - 28 Oct 2012

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