Synlett 2002(5): 0700-0702
DOI: 10.1055/s-2002-25340
LETTER
© Georg Thieme Verlag Stuttgart · New York

Microbial Baeyer-Villiger Oxidation of Bicyclo[4.3.0]ketones by Two Recombinant E. coli Strains. A Novel Access to Indole Alkaloids

Marko D. Mihovilovic*a, Bernhard Müllera, Margaret M. Kayserb, Peter Stanettya
a Vienna University of Technology, Institute of Applied Synthetic Chemistry, Getreidemarkt 9/163-OC, 1060 Vienna, Austria
Fax: +43(1)5880115499; e-Mail: mmihovil@pop.tuwien.ac.at;
b University of New Brunswick, Dept. Phys. Sciences, Saint John, N.B., E2L 4L5, Canada
Further Information

Publication History

Received 27 February 2002
Publication Date:
07 February 2007 (online)

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Abstract

Recombinant Escherichia coli overexpressing Pseudomonas sp. NCIMB 9872 cyclopentanone monooxygenase (CPMO; E.C. 1.14.13.16) and Acinetobacter sp. NCIMB 9871 cyclohexanone monooxygenase (CHMO; E.C. 1.14.13.22) have been utilized in whole-cell biotransformations of prochiral bicyclo[4.3.0]ketones. The lactones produced in a biocatalytic Baeyer-Villiger oxidation represent key intermediates for the synthesis of several indole alkaloids. The two over-expression systems demonstrated a tendency for the formation of opposite enantiomers with CPMO giving (+)-lactones in good yields and excellent enantiomeric excess.