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

• Published in: Journal of molecular catalysis. B, Enzymatic Vol. 11; no. 4-6; pp. 349 - 353
• Main Authors: Mihovilovic, Marko D., Müller, Bernhard, Kayser, Margaret M., Stewart, Jon D., Fröhlich, Johannes, Stanetty, Peter, Spreitzer, Helmut
• Format: Journal Article Conference Proceeding
• Language: English
• Published: Amsterdam Elsevier B.V 22.01.2001; Elsevier Science
• 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; Baeyer-Villiger oxidation; Whole-cell biotransformation; Chemoselective oxidation; Cyclohexanone monooxygenase; Heterocyclic ketones; Recombinant microorganism; Enzyme; Chemoselectivity; Escherichia coli; Ketone; Baeyer Villiger reaction; Biotransformation; Bacteria; Oxidation; Oxidoreductases; Heterocyclic compound; Enterobacteriaceae
• ISSN: 1381-1177; 1873-3158
• DOI: 10.1016/S1381-1177(00)00021-7

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.