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; Bernhard Müller; Margaret M. Kayser; Peter Stanetty

doi:10.1055/s-2002-25340

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Synlett 2002(5): 0700-0702
DOI: 10.1055/s-2002-25340

LETTER

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 Müller^a, Margaret M. Kayser^b, Peter Stanetty^a
^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

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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.

Key words

biocatalysis - recombinant whole-cell biotransformation - monooxygenase - Baeyer-Villiger oxidation - indole alkaloids - enantioselectivity

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Physical and spectroscopic data of lactones 2: (4a R ,8a R )-1,4,4a,5,8,8a-Hexahydro-3 H -2-benzopyran-3-one(2a). Colorless oil; [α]_D ²⁰ = +24.5 (c 1.0, CHCl₃); ee >99% (chiral phase GC); ¹H NMR (200 MHz, CDCl₃): δ = 1.80-2.13 (m, 2 H), 2.16-2.44 (m, 4 H), 2.50-2.60 (m, 2 H), 4.22-4.40 (m, 2 H), 5.67 (br s, 2 H); ¹³C NMR (50 MHz, CDCl₃): δ = 24.0 (t), 28.4 (t), 28.5 (d), 29.6 (d), 33.7 (t), 72.1 (t), 124.1 (d), 124.6 (d), 170.6 (s).
(4a R ,8a R ) - Octahydro-3 H -2-benzopyran-3-one(2b). Colorless oil; [α]_D ²⁰ = +39.1 (c 1.0, CHCl₃); ee = 99% (chiral phase GC); ¹H NMR (200 MHz, CDCl₃): δ = 1.22-1.63 (m, 8 H), 1.83-2.01 (m, 1 H), 2.05-2.25 (m, 1 H), 2.40-2.55 (m, 2 H), 4.25 (d, 2 H, J = 8 Hz); ¹³C NMR (50 MHz, CDCl₃): δ = 21.5 (t), 23.3 (t), 24.6 (t), 28.6 (t), 31.0 (d), 32.7 (d), 32.8 (t), 72.4 (t), 171.1 (s).