DNA-based hydrolytic kinetic resolution of epoxides

被引：43

作者：

Dijk, Ewold W. ^{[1
]}

Feringa, Ben L. ^{[1
]}

Roelfes, Gerard ^{[1
]}

机构：

[1] Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands

来源：

TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 20期

关键词：

D O I：

10.1016/j.tetasy.2008.10.004

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

DNA-bound copper(H) complexes serve as catalysts for the hydrolytic kinetic resolution of 2-pyridyloxiranes in water. Selectivity factors of up to 2.7 were achieved, indicating a chirality transfer of DNA to epoxides via a coordinated metal ion. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：2374 / 2377

页数：4

共 40 条

[1] Synthetic applications of epoxide hydrolases [J].

Archelas, A ;

Furstoss, R .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2001, 5 (02) :112-119

[2] STEREOCHEMISTRY OF RING OPENING OF SOME STILBAZOLE OXIDES [J].

BERTI, G ;

BOTTARI, F ;

LIPPI, G ;

MACCHIA, B .

TETRAHEDRON, 1968, 24 (04) :1959-&

[3]

BERTI G, 1964, ANN CHIM-ROME, V54, P1253

[4] α,β-unsaturated 2-acyl imidazoles as a practical class of dienophiles for the DNA-Based catalytic asymmetric diels-alder reaction in water [J].

Boersma, Arnold J. ;

Feringa, Ben L. ;

Roelfes, Gerard .

ORGANIC LETTERS, 2007, 9 (18) :3647-3650

[5] 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

[6] MICROBIOLOGICAL TRANSFORMATIONS .27. THE 1ST EXAMPLES FOR PREPARATIVE-SCALE ENANTIOSELECTIVE OR DIASTEREOSELECTIVE EPOXIDE HYDROLYZES USING MICROORGANISMS - AN UNEQUIVOCAL ACCESS TO ALL 4 BISABOLOL STEREOISOMERS [J].

CHEN, XJ ;

ARCHELAS, A ;

FURSTOSS, R .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) :5528-5532

[7] 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

[8] DNA-Based catalytic enantioselective Michael reactions in water [J].

Coquiere, David ;

Feringa, Ben L. ;

Roelfes, Gerard .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (48) :9308-9311

[9] Biocatalytic conversion of epoxides [J].

de Vries, EJ ;

Janssen, DB .

CURRENT OPINION IN BIOTECHNOLOGY, 2003, 14 (04) :414-420

[10]

Faber K., 2000, Biotransformations in Organic Chemistry, V4th

← 1 2 3 4 →