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

Shipston, N.F. and Lenn, Michael J. and 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 available from this repository)

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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: Faculties > Science Technology and Medical Studies > School of Biosciences
Depositing User: O.O. Odanye
Date Deposited: 04 Sep 2009 19:29
Last Modified: 28 May 2014 10:39
Resource URI: http://kar.kent.ac.uk/id/eprint/22224 (The current URI for this page, for reference purposes)
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