226546-99-2Relevant articles and documents
Biotransformation of the sesquiterpene (+)-valencene by cytochrome P450cam and P450BM-3
Sowden, Rebecca J.,Yasmin, Samina,Rees, Nicholas H.,Bell, Stephen G.,Wong, Luet-Lok
, p. 57 - 64 (2005)
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 P450 BM-3.
The Preparation and Microbiological Hydroxylation of the Sesquiterpenoid Nootkatone
Arantes, Simone F.,Farooq, Afgan,Hanson, James R.
, p. 801 - 812 (2007/10/03)
The sesquiterpenoid nootkatone has been prepared from valencene by copper(I) iodide catalysed oxidation with t-butylhydroperoxide and hydroxylated at C-9 by Mucor plumbeus and Cephalosporium aphidicola.
