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Baeyer-Villiger oxidations of representative heterocyclic ketones by whole cells of engineered Escherichia coli expressing cyclohexanone monooxygenase |
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| Authors: | Marko D Mihovilovic Bernhard Müller Margaret M Kayser Jon D Stewart Johannes Frhlich Peter Stanetty Helmut Spreitzer |
| Institution: | a Institute for Organic Chemistry, Vienna University of Technology, Getreidemarkt 9, A-1060 Vienna, Austria b Department of Physical Sciences, University of New Brunswick, Saint John, N.B., E2L 4L5, Canada c Department of Chemistry, University of Florida, Gainesville, FL 32611, USA d Institute of Pharm. Chemistry, Vienna University, A-1090 Vienna, Austria |
| Abstract: | 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. |
| Keywords: | Cyclohexanone monooxygenase Baeyer-Villiger oxidation Chemoselective oxidation Heterocyclic ketones Whole-cell biotransformation |
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