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Issue 20, 2005
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Design and synthesis of aromatic inhibitors of anthranilate synthase

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Abstract

Anthranilate synthase catalyses the conversion of chorismate to anthranilate, a key step in tryptophan biosynthesis. A series of 3-(1-carboxy-ethoxy) benzoic acids were synthesised as chorismate analogues, with varying functionality at C-4, the position of the departing hydroxyl group in chorismate. Most of the compounds were moderate inhibitors of anthranilate synthase, with inhibition constants between 20–30 µM. The exception was 3-(1-carboxy-ethoxy) benzoic acid, (C-4 = H), for which KI = 2.4 µM. These results suggest that a hydrogen bonding interaction with the active site general acid (Glu309) is less important than previously assumed for inhibition of the enzyme by these aromatic chorismate analogues.

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

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Publication details

The article was received on 26 Jul 2005, accepted on 16 Aug 2005 and first published on 09 Sep 2005


Article type: Paper
DOI: 10.1039/B510633H
Citation: Org. Biomol. Chem., 2005,3, 3629-3635
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    Design and synthesis of aromatic inhibitors of anthranilate synthase

    R. J. Payne, E. M. M. Bulloch, A. D. Abell and C. Abell, Org. Biomol. Chem., 2005, 3, 3629
    DOI: 10.1039/B510633H

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