Asymmetric Baeyer-Villiger biooxidation of α-substituted cyanocyclohexanones:: Influence of the substituent length on regio- and enantioselectivity

被引：18

作者：

Berezina, Nathalie ^{[1
]}

Kozma, Erika ^{[1
]}

Furstoss, Roland ^{[1
]}

Alphand, Veronique ^{[1
]}

机构：

[1] Aix Marseille Univ, Grp Biocatalyse Biosci, CNRS 3005, F-13288 Marseille, France

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2007年 / 349卷 / 11-12期

关键词：

asymmetric Baeyer-Villiger oxidation; biotransformation; cyano-lactone; cyclohexanone monooxygenase; regioselectivity; whole-cell process;

D O I：

10.1002/adsc.200700150

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Cells of Escherichia coli expressing cyclohexanone monooxygenase catalyzed a highly enantioselective Baeyer-Villiger oxidation of a-substituted cyanocyclohexanones, leading to the corresponding enantiopure caprolactones (ees > 97%). Classical kinetic resolution and regiodivergent parallel kinetic resolution patterns were observed, depending on the length of the linear chain at the alpha position. Regioselectivity was compared with that of chemical BV oxidations. Cells revealed an outstanding stability since 50% of the specific BV activity was retained after 42 days of storage, which facilitates their use in biotransformations.

引用

页码：2049 / 2053

页数：5

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