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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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Article information


Submitted
26 Jul 2005
Accepted
16 Aug 2005
First published
09 Sep 2005

Org. Biomol. Chem., 2005,3, 3629-3635
Article type
Paper

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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