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Type: Journal article
Title: Design and synthesis of aromatic inhibitors of anthranilate synthase
Author: Payne, R.
Bulloch, E.
Abell, A.
Abell, C.
Citation: Organic & Biomolecular Chemistry, 2005; 3(20):3629-3635
Publisher: Royal Soc Chemistry
Issue Date: 2005
ISSN: 1477-0520
Statement of
Richard J. Payne, Esther M. M. Bulloch, Andrew D. Abell and Chris Abell
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 K₁ = 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.
Keywords: Serratia marcescens; Benzoates; Chorismic Acid; Anthranilate Synthase; Enzyme Inhibitors; Binding Sites; Enzyme Activation; Molecular Structure; Structure-Activity Relationship; Stereoisomerism; Hydrogen Bonding; Models, Molecular
RMID: 0020064452
DOI: 10.1039/b510633h
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Appears in Collections:Chemistry publications

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