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Enantioselective whole cell and isolated enzyme catalyzed bayer-villiger oxidation of bicyclo[3.2.0]hept-2-en-6-one

Shipston, N.F., Lenn, Michael J., Knowles, Christopher J. (1992) Enantioselective whole cell and isolated enzyme catalyzed bayer-villiger oxidation of bicyclo[3.2.0]hept-2-en-6-one. Journal of Microbiological Methods, 15 (1). pp. 41-52. ISSN 0167-7012. (The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided) (KAR id:22224)

The full text of this publication is not currently available from this repository. You may be able to access a copy if URLs are provided.

Abstract

Bicyclo[3.2.0]hept-2-en-6-one (Fig. 1, 1) was subjected to Baeyer - Villiger type oxidation using whole cells of Acinetobacter NCIMB 9871, Acinetobacter junii, Pseudomonas putida, Rhodococcus coprophilus, Rhodococcus fascians and cyclohexanone monooxygenase which had been purified 20-fold from Acinetobacter NCIMB 9871. In all cases, when the racemic ketone was oxidised, equal quantities of the regioisomeric lactones (-) 1(S),5(R) 2-oxabicyclo[3.3.0]oct-6-en-3-one (Fig.1, 3) and (-)-1 (R), 5(S) 3-oxabicyclo[3.3.0]oct-6-en-2-one (Fig. 1, 4) were formed in high enantiomeric excess. The results were compared with peracid and alkaline peroxide mediated oxidations which showed no enantioselectivity towards the racemic ketone substrate and yielded only low amounts of 3-oxabicyclo[3.3.0]oct-6-en-2-one. Further investigation using purified cyclohexanone monooxygenase showed that the (+)-enantiomer was oxidised to 2-oxabicyclo[3.3.0]oct-6-en-3-one (Fig. 1, 3) whilst the (-)-enantiomer was oxidised to 3-oxabicyclo [3.3.0]oct-6-en-2-one (Fig. 1, 4). Both lactone products have potential applications as chirons for the synthesis of compounds containing cyclopentane and cyclohexane rings. The development of a chiral gas chromatography method allowed the rapid and accurate determination of the enantiomeric purity of bicyclic ketones and lactones.

Item Type: Article
Uncontrolled keywords: acinetobacter; baeyer-villiger oxidation; chiral capillary gas-liquid chromatography; cyclohexanone monooxygenase
Subjects: Q Science > QR Microbiology
Divisions: Divisions > Division of Natural Sciences > Biosciences
Depositing User: O.O. Odanye
Date Deposited: 04 Sep 2009 19:29 UTC
Last Modified: 16 Nov 2021 10:00 UTC
Resource URI: https://kar.kent.ac.uk/id/eprint/22224 (The current URI for this page, for reference purposes)

University of Kent Author Information

Knowles, Christopher J..

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