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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页码：701 / 705

页数：5

相关论文

共 59 条

[1]

[Anonymous], 2007, ANGEW CHEM

[2] The asymmetric Suzuki coupling route to axially chiral biaryls [J].

Baudoin, O .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (20) :4223-4229

[3] Origin of enantioselectivity in the Ru(arene)(amino alcohol)-catalyzed transfer hydrogenation of ketones [J].

Brandt, P ;

Roth, P ;

Andersson, PG .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (15) :4885-4890

[4] A site-selective dual anchoring strategy for artificial metalloprotein design [J].

Carey, JR ;

Ma, SK ;

Pfister, TD ;

Garner, DK ;

Kim, HK ;

Abramite, JA ;

Wang, ZL ;

Guo, ZJ ;

Lu, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (35) :10812-10813

[5] Artificial metalloenzymes for enantioselective catalysis based on biotin-avidin [J].

Collot, J ;

Gradinaru, J ;

Humbert, N ;

Skander, M ;

Zocchi, A ;

Ward, TR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (30) :9030-9031

[6] Artificial metalloenzymes for enantio selective catalysis: the phenomenon of protein accelerated catalysis [J].

Collot, J ;

Humbert, N ;

Skander, M ;

Klein, G ;

Ward, TR .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (25) :4868-4871

[7] Designed evolution of artificial metalloenzymes: protein catalysts made to order [J].

Creus, Marc ;

Ward, Thomas R. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (12) :1835-1844

[8] A semisynthetic metalloenzyme based on a protein cavity that catalyzes the enantioselective hydrolysis of ester and amide substrates [J].

Davies, RR ;

Distefano, MD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (48) :11643-11652

[9] Chemical modification of biocatalysts [J].

Davis, BG .

CURRENT OPINION IN BIOTECHNOLOGY, 2003, 14 (04) :379-386

[10] Chemical modification of enzymes for enhanced functionality [J].

DeSantis, G ;

Jones, JB .

CURRENT OPINION IN BIOTECHNOLOGY, 1999, 10 (04) :324-330

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