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  • Title: Chemoenzymatic synthesis of 6-phospho-cyclophellitol as a novel probe of 6-phospho-β-glucosidases.
    Author: Kwan DH, Jin Y, Jiang J, Chen HM, Kötzler MP, Overkleeft HS, Davies GJ, Withers SG.
    Journal: FEBS Lett; 2016 Feb; 590(4):461-8. PubMed ID: 26790390.
    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.
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