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

Kwan, David H., Jin, Yi ORCID: https://orcid.org/0000-0002-6927-4371, 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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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.

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:	06 Jan 2024 02:23
URI:	https://orca.cardiff.ac.uk/id/eprint/100308

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