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Issue 1, 2005
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Biotransformation of the sesquiterpene (+)-valencene by cytochrome P450cam and P450BM-3

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Abstract

The sesquiterpenoids are a large class of naturally occurring compounds with biological functions and desirable properties. Oxidation of the sesquiterpene (+)-valencene by wild type and mutants of P450cam from Pseudomonas putida, and of P450BM-3 from Bacillus megaterium, have been investigated as a potential route to (+)-nootkatone, a fine fragrance. Wild type P450cam did not oxidise (+)-valencene but the mutants showed activities up to 9.8 nmol (nmol P450)−1 min−1, with (+)-trans-nootkatol and (+)-nootkatone constituting >85% of the products. Wild type P450BM-3 and mutants had higher activities (up to 43 min−1) than P450cam but were much less selective. Of the many products, cis- and trans-(+)-nootkatol, (+)-nootkatone, cis-(+)-valencene-1,10-epoxide, trans-(+)-nootkaton-9-ol, and (+)-nootkatone-13S,14-epoxide were isolated from whole-cell reactions and characterised. The selectivity patterns suggest that (+)-valencene has one binding orientation in P450cam but multiple orientations in P450BM-3.

Graphical abstract: Biotransformation of the sesquiterpene (+)-valencene by cytochrome P450cam and P450BM-3

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Publication details

The article was received on 25 Aug 2004, accepted on 11 Oct 2004 and first published on 18 Nov 2004


Article type: Paper
DOI: 10.1039/B413068E
Org. Biomol. Chem., 2005,3, 57-64

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    Biotransformation of the sesquiterpene (+)-valencene by cytochrome P450cam and P450BM-3

    R. J. Sowden, S. Yasmin, N. H. Rees, S. G. Bell and L. Wong, Org. Biomol. Chem., 2005, 3, 57
    DOI: 10.1039/B413068E

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