Artificial metalloenzymes for asymmetric allylic alkylation on the basis of the biotin-avidin technology

被引：87

作者：

Pierron, Julien

Malan, Christophe ^{[1
]}

Creus, Marc ^{[1
]}

Gradinaru, Julieta ^{[1
]}

Hafner, Ines ^{[1
]}

Ivanova, Anita ^{[1
]}

Sardo, Alessia ^{[1
]}

Ward, Thomas R. ^{[1
]}

机构：

[1] Univ Neuchatel, Inst Chem, CH-2009 Neuchatel, Switzerland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 04期

关键词：

allylic alkylation; artificial metalloenzymes; asymmetric catalysis; biotin; palladium;

D O I：

10.1002/anie.200703159

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Palladium in the active site: The incorporation of a biotinylated palladium diphosphine within streptavidin yielded an artificial metalloenzyme for the title reaction (see scheme). Chemogenetic optimization of the catalyst by the introduction of a spacer (red star) between biotin (green triangle) and palladium and saturation mutagenesis at position S112X afforded both R- and S-selective artificial asymmetric allylic alkylases. (Chemical Equation Presented) © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

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收藏

页码：701 / 705

页数：5

相关论文

共 59 条

[51] CARBON-CARBON BOND FORMATION VIA PALLADIUM COMPLEXES [J].

TSUJI, J .

ACCOUNTS OF CHEMICAL RESEARCH, 1969, 2 (05) :144-&

[52]

Tsuji J., 2004, PALLADIUM REAGENTS C, DOI DOI 10.1002/0470021209.CH1

[53] Coordinated design of cofactor and active site structures in development of new protein catalysts [J].

Ueno, T ;

Koshiyama, T ;

Ohashi, M ;

Kondo, K ;

Kono, M ;

Suzuki, A ;

Yamane, T ;

Watanabe, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (18) :6556-6562

[54] Design of artificial metalloenzymes using non-covalent insertion of a metal complex into a protein scaffold [J].

Ueno, Takafumi ;

Koshiyama, Tomomi ;

Abe, Satoshi ;

Yokoi, Norihiko ;

Ohashi, Masataka ;

Nakajima, Hiroshi ;

Watanabe, Yoshihito .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2007, 692 (1-3) :142-147

[55] Enantioselective sulfoxidation mediated by vanadium-incorporated phytase:: a hydrolase acting as a peroxidase [J].

van de Velde, F ;

Könemann, L ;

van Rantwijk, F ;

Sheldon, RA .

CHEMICAL COMMUNICATIONS, 1998, (17) :1891-1892

[56] Artificial metalloenzymes for enantioselective catalysis based on the noncovalent incorporation of organometallic moieties in a host protein [J].

Ward, TR .

CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (13) :3798-3804

[57]

Wendt K. U., 2000, ANGEW CHEM, V112, P2930

[58] CONVERSION OF A PROTEIN TO A HOMOGENEOUS ASYMMETRIC HYDROGENATION CATALYST BY SITE-SPECIFIC MODIFICATION WITH A DIPHOSPHINERHODIUM(I) MOIETY [J].

WILSON, ME ;

WHITESIDES, GM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (01) :306-307

[59] Asymmetric hydrogenation with antibody-achiral rhodium complex [J].

Yamaguchi, Hiroyasu ;

Hirano, Tohko ;

Kiminami, Hideaki ;

Taura, Daisuke ;

Harada, Akira .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (19) :3571-3573

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