Issue 20, 2005

Design and synthesis of aromatic inhibitors of anthranilate synthase

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

Article information

Article type
Paper
Submitted
26 juil. 2005
Accepted
16 août 2005
First published
09 sept. 2005

Org. Biomol. Chem., 2005,3, 3629-3635

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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