2005•Polish Journal of ChemistryRequires access

(E)-Cinnamic Acid Analogues as Inhibitors of Phenylalanine Ammonia-Lyase and of Anthocyanin Biosynthesis

Alicja Kluczyk, Borys Szefczyk, Nikolaus Amrhein, Jerzy Zoń

Abstract

Several carboxylic, phosphonic, phosphinic, boronic and nitro analogues of ( £ )-cinnamic acid were synthesized. These and other compounds related to (E)-cinnamic acid were evaluated as potential inhibitors of both phenylalanine ammonia-lyase and of anthocyanin biosynthesis in buckwheat. The most potent inhibition was found for 3-phenylprop-2-ynoic acid (21), however its K i is comparable to K M . The molecular modelling of the interaction of (E)-cinnamic acid (1) and 21 with PAL model suggests some similarities in the binding mode of both compounds.

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Key concepts: Cinnamic acid, Chemistry, Phenylalanine ammonia-lyase, Phenylalanine, Anthocyanin, Biosynthesis, Ammonia, Stereochemistry