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Synthesis of α- And β-galactopyranose-configured isomers of cyclophellitol and cyclophellitol aziridine

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Published copy (DOI)

Author(s)

  • Lianne I. Willems
  • Thomas J. M. Beenakker
  • Benjamin S. Murray
  • Berend Gagestein
  • Hans Van Den Elst
  • Erwin R. van Rijssel
  • Jeroen D C Codée
  • Wouter W. Kallemeijn
  • Johannes M F G Aerts
  • Gijsbert A. Van Der Marel
  • Herman S. Overkleeft

Department/unit(s)

Publication details

JournalEuropean Journal of Organic Chemistry
DatePublished - 14 Aug 2014
Issue number27
Volume2014
Number of pages13
Pages (from-to)6044-6056
Original languageEnglish

Abstract

Cyclophellitol and cyclophellitol aziridine are potent and irreversible mechanism-based inhibitors of retaining β-glucosidases. Alterations in the configuration of these compounds can lead to irreversible inhibition of different classes of retaining glycosidases. We have recently reported on the design of a set of α-galactopyranose-configured cyclophellitol and cyclophellitol aziridine derivatives that inhibit human retaining α-galactosidases. Moreover, we have shown that fluorescently labeled derivatives enable the activity-based profiling of these enzymes in vitro. In this report we describe in detail the synthetic strategies that were used to obtain these epoxide- and aziridine-based probes. In addition, we describe the parallel synthesis of a set of β-galactopyranose-configured cyclophellitol isomers as putative inhibitors of retaining β-galactosidases.

    Research areas

  • Aziridines, Cyclitols, Enzyme inhibitors, Epoxides, Fluorescent probes, Irreversible inhibitors

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