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

DOI: 10.1002/1873-3468.12059 DOI Help

Authors: David H. Kwan (University of British Columbia) , Yi Jin (University of York) , Jianbing Jiang (Leiden University) , Hong-Ming Chen (University of British Columbia) , Miriam P. Kötzler (University of British Columbia) , Herman S. Overkleeft (Leiden University) , Gideon Davies (University of York) , Stephen G. Withers (University of British Columbia)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Febs Letters

State: Published (Approved)
Published: January 2016
Diamond Proposal Number(s): 9948

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-?-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 Keywords: activity-based probes; CAZy GH1; epoxides; Glycosidase inhibitors; sugar-6-phosphate

Diamond Keywords: Enzymes; Bacteria

Subject Areas: Biology and Bio-materials

Instruments: I04-Macromolecular Crystallography

Added On: 16/02/2016 11:26

Discipline Tags:

Structural biology Life Sciences & Biotech

Technical Tags:

Diffraction Macromolecular Crystallography (MX)