Synthesis and mode of action of 1-substituted trans-cyclopropane 1,2-dicarboxylic acids: inhibitors of the methylaspartase reaction

Chemical Communications Pub Date: 1900-01-01 DOI: 10.1039/CC9960000675

Abstract

A range of 1-substituted cyclopropane 1,2-dicarboxylic acids are synthesised using short efficient routes and are found to be good to potent inhibitors of 3-methylaspartase; the crystallographically determined absolute stereochemistry and the mode of action of the most potent inhibitor, (1S,2S)-1-methylcyclopropane 1,2-dicarboxylic acid, is consistent with it acting as a transition state analogue for the central substrate deamination reaction catalysed by the enzyme.

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