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 Ki 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.
The phytochromes are the best studied plant photoreceptors, controlling a wide variety of responses at both whole plant and single cell levels. Three signal transduction pathways, dependent on cGMP and/or calcium, have been found to be utilized by phytochrome to control the expression of genes required for chloroplast development (e.g., CAB and FNR) and anthocyanin biosynthesis (e.g., CHS). In particular, cGMP is a second messenger positively regulating CHS gene expression whilst calcium and calmodulin act as negative regulators. In addition to phytochrome regulation of CHS we have begun to examine the signal transduction pathways utilized by UV photoreceptors. In contrast to phytochrome-mediated responses, results indicate a role for calcium and calmodulin as positive regulators of CHS gene expression in UV light.
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