Regio- and stereoselective oxidation of unactivated C-H bonds with Rhodococcus rhodochrous

被引：6

作者：

O'Reilly, Elaine ^{[1
]}

Aitken, Suzanne J. ^{[1
]}

Grogan, Gideon ^{[2
]}

Kelly, Paul P. ^{[1
]}

Turner, Nicholas J. ^{[1
]}

Flitsch, Sabine L. ^{[1
]}

机构：

[1] Univ Manchester, Sch Chem, Manchester Interdisciplinary Bioctr, Manchester M1 7ND, Lancs, England

[2] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 8卷

基金：

英国生物技术与生命科学研究理事会;

关键词：

biocatalysis; cytochrome P450; hydroxylation; Rhodococcus rhodochrous; selective C-H activation; DRUG METABOLITE SYNTHESIS; BASSIANA ATCC 7159; P450; BM-3; HYDROXYLATION; ENZYMES; BIOHYDROXYLATION;

D O I：

10.3762/bjoc.8.56

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ability of Rhodococcus rhodochrous (NCIMB 9703) to catalyse the regio- and stereoselective hydroxylation of a range of benzyloxy-substituted heterocycles has been investigated. Incubation of 2-benzyloxytetrahydropyrans with resting cell suspensions of the organism yielded predominantly a mixture of 5-hydroxylated isomers in combined yields of up to 40%. Exposure of the corresponding 2-benzyloxytetrahydrofuran derivatives to the cell suspensions gave predominantly the 4-hydroxylated isomers in yields of up to 26%. Most interestingly, 2-(4-nitrobenzyloxy)tetrahydrofuran and 2-(4-nitrobenzyloxy)tetrahydropyran were transformed in high yields to the 4-hydroxylated and 5-hydroxylated products, respectively.

引用

页码：496 / 500

页数：5

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