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|Title:||Design and synthesis of aromatic inhibitors of anthranilate synthase|
|Citation:||Organic & Biomolecular Chemistry, 2005; 3(20):3629-3635|
|Publisher:||Royal Soc Chemistry|
|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|
|Appears in Collections:||Chemistry publications|
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