By the same authors

From the same journal

Chemoenzymatic synthesis of 6-phospho-cyclophellitol as a novel probe of 6-phospho-β-glucosidases

Research output: Contribution to journalArticle

Published copy (DOI)

Author(s)

  • David H. Kwan
  • Yi Jin
  • Jianbing Jiang
  • Hong Ming Chen
  • Miriam P. Kötzler
  • Herman S. Overkleeft
  • Gideon J. Davies
  • Stephen G. Withers

Department/unit(s)

Publication details

JournalFEBS Letters
DateAccepted/In press - 22 Dec 2015
DatePublished (current) - 14 Feb 2016
Issue number4
Volume590
Number of pages8
Pages (from-to)461-468
Original languageEnglish

Abstract

Covalent, mechanism-based inhibitors of glycosidases are valuable probe molecules for visualizing enzyme activities in complex systems. We, here, describe the chemoenzymatic synthesis of 6-phospho-cyclophellitol and evaluate its behaviour as a mechanism-based inactivator of the Streptococcus pyogenes 6-phospho-β-glucosidase from CAZy family GH1. We further present the three-dimensional structure of the inactivated enzyme, which reveals the constellation of active site residues responsible for the enzyme's specificity and confirms the covalent nature of the inactivation.

    Research areas

  • activity-based probes, CAZy GH1, epoxides, Glycosidase inhibitors, sugar-6-phosphate

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