Regioselective Enzymatic β-Carboxylation of para-Hydroxystyrene Derivatives Catalyzed by Phenolic Acid Decarboxylases

被引：42

作者：

Wuensch, Christiane ^{[1
,2
]}

Pavkov-Keller, Tea ^{[1
,3
]}

Steinkellner, Georg ^{[1
,3
]}

Gross, Johannes ^{[1
,2
]}

Fuchs, Michael ^{[2
]}

Hromic, Altijana ^{[1
,3
]}

Lyskowski, Andrzej ^{[1
,3
]}

Fauland, Kerstin ^{[1
,3
]}

Gruber, Karl ^{[3
]}

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

Faber, Kurt ^{[2
]}

机构：

[1] Graz Univ, Dept Chem Organ & Bioorgan Chem, Austrian Ctr Ind Biotechnol, 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：

ADVANCED SYNTHESIS & CATALYSIS | 2015年 / 357卷 / 08期

基金：

奥地利科学基金会;

关键词：

biotransformations; enzyme catalysis; para-hydroxystyrenes; phenolic acid decarboxylases; reaction mechanism; regioselective carboxylation; VANILLYL-ALCOHOL OXIDASE; GAMMA-RESORCYLIC ACID; CARBON-DIOXIDE; ACTIVE-SITE; 2,6-DIHYDROXYBENZOATE DECARBOXYLASE; PURIFICATION; HYDROCARBOXYLATION; ALKYNES; 1,3-DIHYDROXYBENZENE; RESORCINOL;

D O I：

10.1002/adsc.201401028

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

We report on a 'green' method for the utilization of carbon dioxide as C-1 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.

引用

页码：1909 / 1918

页数：10

共 77 条

[1] PHENIX: a comprehensive Python']Python-based system for macromolecular structure solution [J].

Adams, Paul D. ;

Afonine, Pavel V. ;

Bunkoczi, Gabor ;

Chen, Vincent B. ;

Davis, Ian W. ;

Echols, Nathaniel ;

Headd, Jeffrey J. ;

Hung, Li-Wei ;

Kapral, Gary J. ;

Grosse-Kunstleve, Ralf W. ;

McCoy, Airlie J. ;

Moriarty, Nigel W. ;

Oeffner, Robert ;

Read, Randy J. ;

Richardson, David C. ;

Richardson, Jane S. ;

Terwilliger, Thomas C. ;

Zwart, Peter H. .

ACTA CRYSTALLOGRAPHICA SECTION D-STRUCTURAL BIOLOGY, 2010, 66 :213-221

[2] (E)-4-(ALPHA-HALO-PARA-TOLYL)-2-OXO-3-BUTENOIC ACIDS INHIBIT YEAST PYRUVATE DECARBOXYLASE BY A DIVERSITY OF MECHANISMS - MULTIPLE FATE FOR THE THIAMINE-BOUND ENAMINE INTERMEDIATE [J].

ANNAN, N ;

PARIS, R ;

JORDAN, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (24) :8895-8901

[3]

[Anonymous], 2013, ANGEW CHEM

[4]

[Anonymous], ANGEW CHEM

[5]

[Anonymous], PYMOL MOL GRAPH SYST

[6]

[Anonymous], 1987, ANGEW CHEM

[7]

[Anonymous], ANGEW CHEM

[8]

[Anonymous], 2011, ANGEW CHEM-GER EDIT

[9] Catalysis for the Valorization of Exhaust Carbon: from CO2 to Chemicals, Materials, and Fuels. Technological Use of CO2 [J].

Aresta, Michele ;

Dibenedetto, Angela ;

Angelini, Antonella .

CHEMICAL REVIEWS, 2014, 114 (03) :1709-1742

[10] A ternary complex of hydroxycinnamoyl-CoA hydratase-lyase (HCHL) with acetyl-CoA and vanillin gives insights into substrate specificity and mechanism [J].

Bennett, Joseph P. ;

Bertin, Lucille ;

Moulton, Benjamin ;

Fairlamb, Ian J. S. ;

Brzozowski, A. Marek ;

Walton, Nicholas J. ;

Grogan, Gideon .

BIOCHEMICAL JOURNAL, 2008, 414 (02) :281-289

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