D. H. Kim, Suhman Chung
Sep 24, 1999
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Influential Citations
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Journal
Tetrahedron-asymmetry
Abstract
Abstract Both enantiomers of 2-benzyl-3-formylpropanoic acid were synthesized in five steps starting with hydrocinnamic acid and each enantiomer assayed for inhibitory activity against carboxypeptidase A to find that the ( R )-form is 674-fold more potent than its enantiomer. The finding that the ( R )-form which belongs to the l -series is mostly responsible for the inhibitory activity accords with the explanation that the present inhibitor is a transition state analog inhibitor because, as such, its stereochemistry should belong to the same series as that of the substrate, i.e., the l -series. The gem -diol form of the inhibitor generated in situ mimics the transition state in the catalytic process.