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Publication Abstract from PubMed

We report on a 'green' method for the utilization of carbon dioxide as C1 unit for the regioselective synthesis of (E)-cinnamic acids via regioselective enzymatic carboxylation of para-hydroxystyrenes. Phenolic acid decarboxylases from bacterial sources catalyzed the beta-carboxylation of para-hydroxystyrene derivatives with excellent regio- and (E/Z)-stereoselectivity by exclusively acting at the beta-carbon atom of the C=C side chain to furnish the corresponding (E)-cinnamic acid derivatives in up to 40% conversion at the expense of bicarbonate as carbon dioxide source. Studies on the substrate scope of this strategy are presented and a catalytic mechanism is proposed based on molecular modelling studies supported by mutagenesis of amino acid residues in the active site.

Regioselective Enzymatic beta-Carboxylation of -Hydroxy- styrene Derivatives Catalyzed by Phenolic Acid Decarboxylases.,Wuensch C, Pavkov-Keller T, Steinkellner G, Gross J, Fuchs M, Hromic A, Lyskowski A, Fauland K, Gruber K, Glueck SM, Faber K Adv Synth Catal. 2015 May 26;357(8):1909-1918. Epub 2015 Apr 2. PMID:26190963^[1]

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.