Journal article

Publication year: 2010

Pages: 457-462

Journal: Bioresource Technology

Volume number: 101

Issue number: 2

ISSN: 0960-8524

DOI Link: https://doi.org/10.1016/j.biortech.2009.08.087

Publisher: Elsevier

Abstract: 
A selective and highly efficient allylic oxidation of the sesquiterpene (+)-valencene to the grapefruit flavour compound (+)-nootkatone was achieved with lyophilisate of the edible mushroom Pleurotus sapidus. The catalytic reaction sequence was elucidated through the identification of intermediate, (+)-valencene derived hydroperoxides. A specific staining of hydroperoxides allowed the semi-preparative isolation of two secondary (+)-valencene hydroperoxides, 6(R)-Isopropenyl-4(R),4a(S)-dimethyl-2,3,4,4a,5,6,7,8-octahydro-naphthalen-4(S)-yl-hydroperoxide and 6(R)-Isopropenyl-4(R),4a(S)-dimethyl-2,3,4,4a,5,6,7,8-8-octahydro-naphthalen-2(R)-yl-hydroperoxide. Chemical reduction of the biotransformation products yielded a tertiary alcohol identified as 2(R)-Isopropenyl-S(R),8a(S)-dimethyl-1,3,4,7,8,8a-hexahydro-2H-naphthalen-4a(R)-ol. This suggested a lipoxygenase-type oxidation of (+)-valencene via secondary and tertiary hydroperoxides and confirmed homology data of the key enzyme obtained previously from amino acid sequencing.

Harvard Citation style: Krügener, S., Krings, U., Zorn, H. and Berger, R. (2010) A dioxygenase of Pleurotus sapidus transforms (+)-valencene regio-specifically to (+)-nootkatone via a stereo-specific allylic hydroperoxidation, Bioresource Technology, 101(2), pp. 457-462. https://doi.org/10.1016/j.biortech.2009.08.087

APA Citation style: Krügener, S., Krings, U., Zorn, H., & Berger, R. (2010). A dioxygenase of Pleurotus sapidus transforms (+)-valencene regio-specifically to (+)-nootkatone via a stereo-specific allylic hydroperoxidation. Bioresource Technology. 101(2), 457-462. https://doi.org/10.1016/j.biortech.2009.08.087