5m1i › Citations

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

Figure 1
Figure 2
Scheme 1
Adamson C, Pengelly RJ, Shamsi Kazem Abadi S, Chakladar S, Draper J, Britton R, Gloster TM, Bennet AJ
OpenAccess logo Angew Chem Int Ed Engl 55 14978-14982 (2016)
Related entries: 5m0x, 5m12, 5m16

Cited: 14 times
EuropePMC logo PMID: 27783466

Abstract

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 H3 conformations. We also report the synthesis and reactivity of a fluorinated analogue and the structure of its covalently linked intermediate (flattened 2 H3 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.

Articles - 5m1i mentioned but not cited (1)

  1. Activity-based metaproteomics driven discovery and enzymological characterization of potential α-galactosidases in the mouse gut microbiome. Jiang J, Czuchry D, Ru Y, Peng H, Shen J, Wang T, Zhao W, Chen W, Sui SF, Li Y, Li N. Commun Chem 7 184 (2024)


Reviews citing this publication (1)

  1. Applications of alkyl orthoesters as valuable substrates in organic transformations, focusing on reaction media. Khademi Z, Nikoofar K. RSC Adv 10 30314-30397 (2020)

Articles citing this publication (12)



Quick links