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 Mär 2005
Accepted
15 Apr 2005
First published
06 Mai 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements