Design and synthesis of substrate-mimic inhibitors of mycothiol-S-conjugate amidase from Mycobacterium tuberculosis

BB Metaferia, S Ray, JA Smith, CA Bewley

Index: Metaferia, Belhu B.; Ray, Satyajit; Smith, Jeremy A.; Bewley, Carole A. Bioorganic and Medicinal Chemistry Letters, 2007 , vol. 17, # 2 p. 444 - 447

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Citation Number: 26

Abstract

The Staudinger reaction between a polymer-supported triphenylphosphine reagent and pseudo-disaccharide azides is successfully applied to synthesize a variety of substrate- mimic mycothiol analogs. Screening of this new group of analogs against the mycobacterial detoxification enzyme mycothiol-S-conjugate amidase (MCA) yielded several modest inhibitors (IC50 values around 50μM) and provided additional structure–activity ...