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Issue 19, 2014
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Regioselective ortho-carboxylation of phenols catalyzed by benzoic acid decarboxylases: a biocatalytic equivalent to the Kolbe–Schmitt reaction

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Abstract

The enzyme catalyzed carboxylation of electron-rich phenol derivatives employing recombinant benzoic acid decarboxylases at the expense of bicarbonate as CO2 source is reported. In contrast to the classic Kolbe–Schmitt reaction, the biocatalytic equivalent proceeded in a highly regioselective fashion exclusively at the ortho-position of the phenolic directing group in up to 80% conversion. Several enzymes were identified, which displayed a remarkably broad substrate scope encompassing alkyl, alkoxy, halo and amino-functionalities. Based on the crystal structure and molecular docking simulations, a mechanistic proposal for 2,6-dihydroxybenzoic acid decarboxylase is presented.

Graphical abstract: Regioselective ortho-carboxylation of phenols catalyzed by benzoic acid decarboxylases: a biocatalytic equivalent to the Kolbe–Schmitt reaction

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Supplementary files

Article information


Submitted
17 Dec 2013
Accepted
23 Jan 2014
First published
27 Jan 2014

RSC Adv., 2014,4, 9673-9679
Article type
Paper

Regioselective ortho-carboxylation of phenols catalyzed by benzoic acid decarboxylases: a biocatalytic equivalent to the Kolbe–Schmitt reaction

C. Wuensch, J. Gross, G. Steinkellner, A. Lyskowski, K. Gruber, S. M. Glueck and K. Faber, RSC Adv., 2014, 4, 9673
DOI: 10.1039/C3RA47719C

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