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

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.

journal_name

FEBS Lett

journal_title

FEBS letters

authors

Kwan DH,Jin Y,Jiang J,Chen HM,Kötzler MP,Overkleeft HS,Davies GJ,Withers SG

doi

10.1002/1873-3468.12059

subject

Has Abstract

pub_date

2016-02-01 00:00:00

pages

461-8

issue

4

eissn

0014-5793

issn

1873-3468

journal_volume

590

pub_type

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