Artificial Transfer Hydrogenases for the Enantioselective Reduction of Cyclic Imines

被引：109

作者：

Duerrenberger, Marc ^{[1
]}

Heinisch, Tillmann ^{[1
]}

Wilson, Yvonne M. ^{[1
]}

Rossel, Thibaud ^{[1
]}

Nogueira, Elisa ^{[1
]}

Knoerr, Livia ^{[1
]}

Mutschler, Annette ^{[1
]}

Kersten, Karoline ^{[1
]}

Zimbron, Malcolm Jeremy ^{[1
]}

Pierron, Julien ^{[1
]}

Schirmer, Tilman ^{[1
]}

Ward, Thomas R. ^{[1
]}

机构：

[1] Univ Basel, Inst Anorgan Chem, CH-4056 Basel, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 13期

基金：

瑞士国家科学基金会;

关键词：

artificial metalloenzymes; asymmetric catalysis; imine reduction; piano stool complexes; transfer hydrogenation; ASYMMETRIC TRANSFER HYDROGENATION; DIRECTED EVOLUTION; AMINATION; CATALYSTS; COMPLEX; KETONES; DESIGN; SITE;

D O I：

10.1002/anie.201007820

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Man-made activity: Introduction of a biotinylated iridium piano stool complex within streptavidin affords an artificial imine reductase (see scheme). Saturation mutagenesis allowed optimization of the activity and the enantioselectivity of this metalloenzyme, and its X-ray structure suggests that a nearby lysine residue acts as a proton source during the transfer hydrogenation. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：3026 / 3029

页数：4

共 41 条

[1]

Abe S, 2009, TOP ORGANOMETAL CHEM, V25, P25, DOI 10.1007/3418_2008_4

[2] Mechanistic investigation on the hydrogenation of imines by [p-(Me2CH)C6H4Me]RuH(NH2CHPhCHPhNSO2C6H4-p-CH3).: Experimental support for an ionic pathway [J].

Aberg, Jenny B. ;

Samec, Joseph S. M. ;

Baeckvall, Jan-E. .

CHEMICAL COMMUNICATIONS, 2006, (26) :2771-2773

[3]

[Anonymous], 2009, ANGEW CHEM, DOI DOI 10.1002/ANGE.200902570

[4] Kinetic studies of the asymmetric transfer hydrogenation of imines with formic acid catalyzed by Rh-diamine catalysts [J].

Blackmond, Donna G. ;

Ropic, Melanie ;

Stefinovic, Marijan .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2006, 10 (03) :457-463

[5] Mechanisms of the H2-hydrogenation and transfer hydrogenation of polar bonds catalyzed by ruthenium hydride complexes [J].

Clapham, SE ;

Hadzovic, A ;

Morris, RH .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2201-2237

[6]

Creus M., 2008, ANGEW CHEM, V120, P1422

[7] X-ray structure and designed evolution of an artificial transfer hydrogenase [J].

Creus, Marc ;

Pordea, Anca ;

Rossel, Thibaud ;

Sardo, Alessia ;

Letondor, Christophe ;

Ivanova, Anita ;

Le Trong, Isolde ;

Stenkamp, Ronald E. ;

Ward, Thomas R. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (08) :1400-1404

[8]

Deuss P. J., 2010, ANGEW CHEM, V122, P5443

[9] Highly Efficient and Site-Selective Phosphane Modification of Proteins through Hydrazone Linkage: Development of Artificial Metalloenzymes [J].

Deuss, Peter J. ;

Popa, Gina ;

Botting, Catherine H. ;

Laan, Wouter ;

Kamer, Paul C. J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (31) :5315-5317

[10] A Highly Enantioselective Access to Tetrahydroisoquinoline and β-Carboline Alkaloids with Simple Noyori-Type Catalysts in Aqueous Media [J].

Evanno, Laurent ;

Ormala, Joel ;

Pihko, Petri M. .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (47) :12963-12967

← 1 2 3 4 5 →