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From the same journal

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

Research output: Contribution to journalArticle

Published copy (DOI)

Author(s)

  • 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

Department/unit(s)

Publication details

JournalChemical Communications
DatePublished - 28 Oct 2012
Issue number84
Volume48
Number of pages3
Pages (from-to)10386-10388
Original languageEnglish

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.

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