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

Kwan, David H., Jin, Yi, Jiang, Jianbing, Chen, Hong-Ming, Kötzler, Miriam P., Overkleeft, Herman S., Davies, Gideon J. and Withers, Stephen G. 2016. Chemoenzymatic synthesis of 6-phospho-cyclophellitol as a novel probe of 6-phospho-β-glucosidases. FEBS Letters 590 (4) , pp. 461-468. 10.1002/1873-3468.12059

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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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: Activity-based probes; CAZy GH1; Epoxides; Glycosidase inhibitors; Sugar-6-phosphate
Publisher: Wiley
ISSN: 1873-3468
Date of Acceptance: 22 December 2015
Last Modified: 04 Jun 2017 09:49

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