Resolution of fused bicyclic ketones by a recombinant biocatalyst expressing the Baeyer-Villiger monooxygenase gene Rv3049c from Mycobacterium tuberculosis H37Rv

Radka Snajdrova; Gideon Grogan; Marko D. Mihovilovic

doi:10.1016/j.bmcl.2006.06.072

Resolution of fused bicyclic ketones by a recombinant biocatalyst expressing the Baeyer-Villiger monooxygenase gene Rv3049c from Mycobacterium tuberculosis H37Rv

Radka Snajdrova, Gideon Grogan, Marko D. Mihovilovic

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Recombinant Escherichia coli B834 (DE3) pDB5 expressing the Rv3049c gene encoding a Baeyer-Villiger monooxygenase from Mycobacterium tuberculosis H37Rv was used for regioselective oxidations of fused bicyclic ketones. This whole-cell system represents the first recombinant Baeyer-Villiger oxidation biocatalyst that effectively resolves the racemic starting materials in this series. Within biotransformations using this organism one substrate enantiomer remains in high optical purity, while the second enantiomer is oxidized to one type of regioisomeric lactone preferably. (c) 2006 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	4813-4817
Number of pages	5
Journal	Bioorganic & Medicinal Chemistry Letters
Volume	16
Issue number	18
DOIs	https://doi.org/10.1016/j.bmcl.2006.06.072
Publication status	Published - 15 Sept 2006

Keywords

Baeyer-Villiger oxidation
biocatalysis
biotransformation
lactone
monooxygenase
ENGINEERED ESCHERICHIA-COLI
MICROBIOLOGICAL TRANSFORMATIONS
WHOLE-CELLS
OXIDATIONS
CLONING
ROUTE

Access to Document

10.1016/j.bmcl.2006.06.072

Cite this

@article{015e6c1cf58844188522773da2df62c4,

title = "Resolution of fused bicyclic ketones by a recombinant biocatalyst expressing the Baeyer-Villiger monooxygenase gene Rv3049c from Mycobacterium tuberculosis H37Rv",

abstract = "Recombinant Escherichia coli B834 (DE3) pDB5 expressing the Rv3049c gene encoding a Baeyer-Villiger monooxygenase from Mycobacterium tuberculosis H37Rv was used for regioselective oxidations of fused bicyclic ketones. This whole-cell system represents the first recombinant Baeyer-Villiger oxidation biocatalyst that effectively resolves the racemic starting materials in this series. Within biotransformations using this organism one substrate enantiomer remains in high optical purity, while the second enantiomer is oxidized to one type of regioisomeric lactone preferably. (c) 2006 Elsevier Ltd. All rights reserved.",

keywords = "Baeyer-Villiger oxidation, biocatalysis, biotransformation, lactone, monooxygenase, ENGINEERED ESCHERICHIA-COLI, MICROBIOLOGICAL TRANSFORMATIONS, WHOLE-CELLS, OXIDATIONS, CLONING, ROUTE",

author = "Radka Snajdrova and Gideon Grogan and Mihovilovic, {Marko D.}",

year = "2006",

month = sep,

day = "15",

doi = "10.1016/j.bmcl.2006.06.072",

language = "English",

volume = "16",

pages = "4813--4817",

journal = "Bioorganic & Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier",

number = "18",

}

Resolution of fused bicyclic ketones by a recombinant biocatalyst expressing the Baeyer-Villiger monooxygenase gene Rv3049c from Mycobacterium tuberculosis H37Rv. / Snajdrova, Radka; Grogan, Gideon; Mihovilovic, Marko D.
In: Bioorganic & Medicinal Chemistry Letters, Vol. 16, No. 18, 15.09.2006, p. 4813-4817.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Resolution of fused bicyclic ketones by a recombinant biocatalyst expressing the Baeyer-Villiger monooxygenase gene Rv3049c from Mycobacterium tuberculosis H37Rv

AU - Snajdrova, Radka

AU - Grogan, Gideon

AU - Mihovilovic, Marko D.

PY - 2006/9/15

Y1 - 2006/9/15

N2 - Recombinant Escherichia coli B834 (DE3) pDB5 expressing the Rv3049c gene encoding a Baeyer-Villiger monooxygenase from Mycobacterium tuberculosis H37Rv was used for regioselective oxidations of fused bicyclic ketones. This whole-cell system represents the first recombinant Baeyer-Villiger oxidation biocatalyst that effectively resolves the racemic starting materials in this series. Within biotransformations using this organism one substrate enantiomer remains in high optical purity, while the second enantiomer is oxidized to one type of regioisomeric lactone preferably. (c) 2006 Elsevier Ltd. All rights reserved.

AB - Recombinant Escherichia coli B834 (DE3) pDB5 expressing the Rv3049c gene encoding a Baeyer-Villiger monooxygenase from Mycobacterium tuberculosis H37Rv was used for regioselective oxidations of fused bicyclic ketones. This whole-cell system represents the first recombinant Baeyer-Villiger oxidation biocatalyst that effectively resolves the racemic starting materials in this series. Within biotransformations using this organism one substrate enantiomer remains in high optical purity, while the second enantiomer is oxidized to one type of regioisomeric lactone preferably. (c) 2006 Elsevier Ltd. All rights reserved.

KW - Baeyer-Villiger oxidation

KW - biocatalysis

KW - biotransformation

KW - lactone

KW - monooxygenase

KW - ENGINEERED ESCHERICHIA-COLI

KW - MICROBIOLOGICAL TRANSFORMATIONS

KW - WHOLE-CELLS

KW - OXIDATIONS

KW - CLONING

KW - ROUTE

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DO - 10.1016/j.bmcl.2006.06.072

M3 - Article

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JO - Bioorganic & Medicinal Chemistry Letters

JF - Bioorganic & Medicinal Chemistry Letters

IS - 18

ER -