100192-55-0Relevant articles and documents
New Class of Glycoside Hydrolase Mechanism-Based Covalent Inhibitors: Glycosylation Transition State Conformations
Shamsi Kazem Abadi, Saeideh,Tran, Michael,Yadav, Anuj K.,Adabala, Pal John Pal,Chakladar, Saswati,Bennet, Andrew J.
supporting information, p. 10625 - 10628 (2017/08/15)
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.