Journal of the American Chemical Society
Journal of the American Chemical Society
5 years ago

New Class of Glycoside Hydrolase Mechanism-Based Covalent Inhibitors: Glycosylation Transition State Conformations

New Class of Glycoside Hydrolase Mechanism-Based Covalent Inhibitors: Glycosylation Transition State Conformations
Pal John Pal Adabala, Michael Tran, Saeideh Shamsi Kazem Abadi, Saswati Chakladar, Anuj K. Yadav, Andrew J. Bennet
The design of covalent inhibitors in glycoscience research is important for the development of chemical biology probes. Here we report the synthesis of a new carbocyclic mechanism-based covalent inhibitor of an α-glucosidase. The enzyme efficiently catalyzes its alkylation via either an allylic cation or a cationic transition state. We show this allylic covalent inhibitor has different catalytic proficiencies for pseudoglycosylation and deglycosylation. Such inhibitors have the potential to be useful chemical biology tools.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b05065

DOI: 10.1021/jacs.7b05065

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