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

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

Content Provider	Royal Society of Chemistry (RSC)
Author	Gruber, Karl Gross, Johannes Lyskowski, Andrzej Glueck, Silvia M. Faber, Kurt Wuensch, Christiane Steinkellner, Georg
Copyright Year	2014
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.
Starting Page	9673
Ending Page	9679
Page Count	7
File Format	HTM / HTML PDF
ISSN	20462069
Volume Number	4
Issue Number	19
Journal	RSC Advances
DOI	10.1039/c3ra47719c
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Bicarbonate Phenol Dihydroxybenzoic acid Schmitt Enzyme Alkyl Docking (molecular) Carboxylation Kolbe\u2013Schmitt reaction Kolbe
Content Type	Text
Resource Type	Article
Subject	Chemistry Chemical Engineering

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