(E)-cinnamic acid analogues as inhibitors of phenylalanine ammonia-lyase and of anthocyanin biosynthesis

Abstract

Several carboxylic, phosphonic, phosphinic, boronic and nitro analogues of (E)-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 KM. 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.