Regioselective enzymatic carboxylation of phenols and hydroxystyrene derivatives

Christiane Wuensch; Silvia M Glueck; Johannes Gross; Dominik Koszelewski; Markus Schober; Kurt Faber

doi:10.1021/ol300385k

Regioselective enzymatic carboxylation of phenols and hydroxystyrene derivatives

Org Lett. 2012 Apr 20;14(8):1974-7. doi: 10.1021/ol300385k. Epub 2012 Apr 3.

Authors

Christiane Wuensch¹, Silvia M Glueck, Johannes Gross, Dominik Koszelewski, Markus Schober, Kurt Faber

Affiliation

¹ Austrian Centre of Industrial Biotechnology, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria.

Abstract

The enzymatic carboxylation of phenol and styrene derivatives using (de)carboxylases in carbonate buffer proceeded in a highly regioselective fashion: Benzoic acid (de)carboxylases selectively formed o-hydroxybenzoic acid derivatives, phenolic acid (de)carboxylases selectively acted at the β-carbon atom of styrenes forming (E)-cinnamic acids.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carboxy-Lyases / metabolism*
Cinnamates / chemical synthesis*
Cinnamates / chemistry
Combinatorial Chemistry Techniques
Hydroxybenzoates / chemical synthesis*
Hydroxybenzoates / chemistry
Molecular Structure
Phenols / chemistry*
Stereoisomerism
Styrenes / chemistry*

Substances

Cinnamates
Hydroxybenzoates
Phenols
Styrenes
cinnamic acid
Carboxy-Lyases