Issue 12, 2005

Design and synthesis of aromatic inhibitors of anthranilate synthase

Abstract

Aromatic analogues of chorismate were synthesised as potential inhibitors of anthranilate synthase. Molecular modelling using GOLD2.1 showed that these analogues docked into the active site of Serratia marcescens anthranilate synthase in the same conformation as chorismate. Most compounds were found to be micromolar inhibitors of S. marcescens anthranilate synthase. The most potent analogue, 3-(1-carboxy-ethoxy)-4-hydroxybenzoate (KI 3 µM), included a lactyl ether side chain. This appears to be a good replacement for the enol-pyruvyl side chain of chorismate.

Graphical abstract: Design and synthesis of aromatic inhibitors of anthranilate synthase

Article information

Article type
Paper
Submitted
15 Нау. 2005
Accepted
15 Сәу. 2005
First published
06 Мам. 2005

Org. Biomol. Chem., 2005,3, 2271-2281

Design and synthesis of aromatic inhibitors of anthranilate synthase

R. J. Payne, M. D. Toscano, E. M. M. Bulloch, A. D. Abell and C. Abell, Org. Biomol. Chem., 2005, 3, 2271 DOI: 10.1039/B503802B

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