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New Class of Glycoside Hydrolase Mechanism-Based Covalent Inhibitors: Glycosylation Transition State Conformations
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2017-07-26 00:00:00 , DOI: 10.1021/jacs.7b05065 Saeideh Shamsi Kazem Abadi 1 , Michael Tran 1 , Anuj K. Yadav 1 , Pal John Pal Adabala 1 , Saswati Chakladar 1 , Andrew J. Bennet 1
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2017-07-26 00:00:00 , DOI: 10.1021/jacs.7b05065 Saeideh Shamsi Kazem Abadi 1 , Michael Tran 1 , Anuj K. Yadav 1 , Pal John Pal Adabala 1 , Saswati Chakladar 1 , Andrew J. Bennet 1
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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.
更新日期：2017-07-28
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