Regio- and stereoselective oxidation of unactivated C–H bonds with Rhodococcus rhodochrous
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...
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doaj-b02b817aa61845d582b500b249b1ba9c2021-02-02T07:50:16ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972012-04-018149650010.3762/bjoc.8.561860-5397-8-56Regio- and stereoselective oxidation of unactivated C–H bonds with Rhodococcus rhodochrousElaine O’Reilly0Suzanne J. Aitken1Gideon Grogan2Paul P. Kelly3Nicholas J. Turner4Sabine L. Flitsch5School of Chemistry, Manchester Interdisciplinary Biocentre, The University of Manchester, 131 Princess Street, Manchester, M1 7ND, UK, Fax: +44 (0)161 2751311, Tel: +44 (0)161 3065172School of Chemistry, Manchester Interdisciplinary Biocentre, The University of Manchester, 131 Princess Street, Manchester, M1 7ND, UK, Fax: +44 (0)161 2751311, Tel: +44 (0)161 3065172Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK, Tel: +44 (0)1904 328256School of Chemistry, Manchester Interdisciplinary Biocentre, The University of Manchester, 131 Princess Street, Manchester, M1 7ND, UK, Fax: +44 (0)161 2751311, Tel: +44 (0)161 3065172School of Chemistry, Manchester Interdisciplinary Biocentre, The University of Manchester, 131 Princess Street, Manchester, M1 7ND, UK, Fax: +44 (0)161 2751311, Tel: +44 (0)161 3065172School of Chemistry, Manchester Interdisciplinary Biocentre, The University of Manchester, 131 Princess Street, Manchester, M1 7ND, UK, Fax: +44 (0)161 2751311, Tel: +44 (0)161 3065172The 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.https://doi.org/10.3762/bjoc.8.56biocatalysiscytochrome P450hydroxylationRhodococcus rhodochrousselective C–H activation |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Elaine O’Reilly Suzanne J. Aitken Gideon Grogan Paul P. Kelly Nicholas J. Turner Sabine L. Flitsch |
spellingShingle |
Elaine O’Reilly Suzanne J. Aitken Gideon Grogan Paul P. Kelly Nicholas J. Turner Sabine L. Flitsch Regio- and stereoselective oxidation of unactivated C–H bonds with Rhodococcus rhodochrous Beilstein Journal of Organic Chemistry biocatalysis cytochrome P450 hydroxylation Rhodococcus rhodochrous selective C–H activation |
author_facet |
Elaine O’Reilly Suzanne J. Aitken Gideon Grogan Paul P. Kelly Nicholas J. Turner Sabine L. Flitsch |
author_sort |
Elaine O’Reilly |
title |
Regio- and stereoselective oxidation of unactivated C–H bonds with Rhodococcus rhodochrous |
title_short |
Regio- and stereoselective oxidation of unactivated C–H bonds with Rhodococcus rhodochrous |
title_full |
Regio- and stereoselective oxidation of unactivated C–H bonds with Rhodococcus rhodochrous |
title_fullStr |
Regio- and stereoselective oxidation of unactivated C–H bonds with Rhodococcus rhodochrous |
title_full_unstemmed |
Regio- and stereoselective oxidation of unactivated C–H bonds with Rhodococcus rhodochrous |
title_sort |
regio- and stereoselective oxidation of unactivated c–h bonds with rhodococcus rhodochrous |
publisher |
Beilstein-Institut |
series |
Beilstein Journal of Organic Chemistry |
issn |
1860-5397 |
publishDate |
2012-04-01 |
description |
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. |
topic |
biocatalysis cytochrome P450 hydroxylation Rhodococcus rhodochrous selective C–H activation |
url |
https://doi.org/10.3762/bjoc.8.56 |
work_keys_str_mv |
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