Structural Snapshots for Mechanism‐Based Inactivation of a Glycoside Hydrolase by Cyclopropyl Carbasugars | Zendy

Adamson Christopher | Zendy; Pengelly Robert J. | Zendy; Shamsi Kazem Abadi Saeideh | Zendy; Chakladar Saswati | Zendy; Draper Jason | Zendy; Britton Robert | Zendy; Gloster Tracey M. | Zendy; Bennet Andrew J. | Zendy

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Structural Snapshots for Mechanism‐Based Inactivation of a Glycoside Hydrolase by Cyclopropyl Carbasugars

Author(s) -

Adamson Christopher,

Pengelly Robert J.,

Shamsi Kazem Abadi Saeideh,

Chakladar Saswati,

Draper Jason,

Britton Robert,

Gloster Tracey M.,

Bennet Andrew J.

Publication year - 2016

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201607431

Subject(s) - chemistry , stereochemistry , glycoside hydrolase , anomer , reactivity (psychology) , mechanism (biology) , covalent bond , glycoside , carbon atom , combinatorial chemistry , enzyme , biochemistry , organic chemistry , philosophy , medicine , alternative medicine , alkyl , epistemology , pathology

Glycoside hydrolases (GHs) have attracted considerable attention as targets for therapeutic agents, and thus mechanism‐based inhibitors are of great interest. We report the first structural analysis of a carbocyclic mechanism‐based GH inactivator, the results of which show that the two Michaelis complexes are in 2 H 3 conformations. We also report the synthesis and reactivity of a fluorinated analogue and the structure of its covalently linked intermediate (flattened 2 H 3 half‐chair). We conclude that these inactivator reactions mainly involve motion of the pseudo‐anomeric carbon atom, knowledge that should stimulate the design of new transition‐state analogues for use as chemical biology tools.

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