Article ID Journal Published Year Pages File Type
1374612 Bioorganic & Medicinal Chemistry Letters 2010 4 Pages PDF
Abstract

A novel analog of isochorismate, in which the enolpyruvyl substituent is replaced with a carboxymethoxyl group, has been synthesized in four steps from a known intermediate. This analog is more stable than the natural product, but still acts as a good substrate for the enzyme MenD (SEPHCHC synthase). The enzyme consumes the (+)-enantiomer only, with an apparent turnover similar to that of the natural substrate, and an apparent Michaelis constant conveniently higher than that of isochorismate. This analog will be useful in the study of any isochorismate-utilizing enzyme.

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Physical Sciences and Engineering Chemistry Organic Chemistry
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