Baeyer-Villiger oxidations of representative heterocyclic ketones by whole cells of engineered Escherichia coli expressing cyclohexanone monooxygenase

Whole cells of an Escherichia coli strain overexpressing Acinetobacter sp. NCIB 9871 cyclohexanone monooxygenase (CHMO; E.C. 1.14.13.22) have been used for the Baeyer-Villiger oxidation of representative heterocyclic six-membered ketones to probe the potential impact of nitrogen, sulfur and oxygen o...

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Bibliographic Details
Published in:Journal of molecular catalysis. B, Enzymatic Enzymatic, 2001-01, Vol.11 (4-6), p.349-353
Main Authors: Mihovilovic, Marko D., Müller, Bernhard, Kayser, Margaret M., Stewart, Jon D., Fröhlich, Johannes, Stanetty, Peter, Spreitzer, Helmut
Format: Article
Language:English
Subjects:
Baeyer-Villiger oxidation
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Chemoselective oxidation
Cyclohexanone monooxygenase
Fundamental and applied biological sciences. Psychology
Heterocyclic ketones
Methods. Procedures. Technologies
Whole-cell biotransformation
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Summary:Whole cells of an Escherichia coli strain overexpressing Acinetobacter sp. NCIB 9871 cyclohexanone monooxygenase (CHMO; E.C. 1.14.13.22) have been used for the Baeyer-Villiger oxidation of representative heterocyclic six-membered ketones to probe the potential impact of nitrogen, sulfur and oxygen on the chemoselectivity of these reactions. The fact that all of these heterocyclic systems were accepted as substrates by the enzyme and gave normal Baeyer-Villiger products broadens the synthetic utility of the engineered E. coli strain and emphasizes the chemoselectivity achievable with enzymatic oxidation catalysts.
ISSN:1381-1177
1873-3158
DOI:10.1016/S1381-1177(00)00021-7