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

被引：42

作者：

Wuensch, Christiane ^{[1
,2
]}

Gross, Johannes ^{[1
,2
]}

Steinkellner, Georg ^{[1
,3
]}

Lyskowski, Andrzej ^{[1
,3
]}

Gruber, Karl ^{[3
]}

Glueck, Silvia M. ^{[1
,2
]}

Faber, Kurt ^{[2
]}

机构：

[1] Austrian Ctr Ind Biotechnol ACIB GmbH, A-8010 Graz, Austria

[2] Graz Univ, Dept Chem Organ & Bioorgan Chem, A-8010 Graz, Austria

[3] Graz Univ, Inst Mol Biosci, A-8010 Graz, Austria

来源：

RSC ADVANCES | 2014年 / 4卷 / 19期

关键词：

GAMMA-RESORCYLATE DECARBOXYLASE; P-AMINOSALICYLIC ACID; SP STRAIN MTP-10005; CARBON-DIOXIDE; 4-HYDROXYBENZOATE DECARBOXYLASE; NONOXIDATIVE DECARBOXYLATION; CLOSTRIDIUM-HYDROXYBENZOICUM; HYDROXYSTYRENE DERIVATIVES; PURIFICATION; GENE;

D O I：

10.1039/c3ra47719c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：9673 / 9679

页数：7