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Issue 12, 2005
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Design and synthesis of aromatic inhibitors of anthranilate synthase

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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

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Publication details

The article was received on 15 Mar 2005, accepted on 15 Apr 2005 and first published on 06 May 2005


Article type: Paper
DOI: 10.1039/B503802B
Citation: Org. Biomol. Chem., 2005,3, 2271-2281
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    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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