Details
| Original language | English |
|---|---|
| Pages (from-to) | 457-462 |
| Number of pages | 6 |
| Journal | Bioresource technology |
| Volume | 101 |
| Issue number | 2 |
| Publication status | Published - 17 Sept 2009 |
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-octahydro-naphthalen-2(R)-yl-hydroperoxide. Chemical reduction of the biotransformation products yielded a tertiary alcohol identified as 2(R)-Isopropenyl-8(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.
Keywords
- (+)-Valencene hydroperoxide, Nootkatone, Pleurotus sapidus, Valencene dioxygenase
ASJC Scopus subject areas
- Chemical Engineering(all)
- Bioengineering
- Environmental Science(all)
- Environmental Engineering
- Energy(all)
- Renewable Energy, Sustainability and the Environment
- Environmental Science(all)
- Waste Management and Disposal
Sustainable Development Goals
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In: Bioresource technology, Vol. 101, No. 2, 17.09.2009, p. 457-462.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - A dioxygenase of Pleurotus sapidus transforms (+)-valencene regio-specifically to (+)-nootkatone via a stereo-specific allylic hydroperoxidation
AU - Krügener, Sven
AU - Krings, Ulrich
AU - Zorn, Holger
AU - Berger, Ralf G.
N1 - Funding information: Support of the work by the “ Deutsche Bundesstiftung Umwelt ” ( AZ 13187-32 ) is gratefully acknowledged.
PY - 2009/9/17
Y1 - 2009/9/17
N2 - 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-octahydro-naphthalen-2(R)-yl-hydroperoxide. Chemical reduction of the biotransformation products yielded a tertiary alcohol identified as 2(R)-Isopropenyl-8(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.
AB - 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-octahydro-naphthalen-2(R)-yl-hydroperoxide. Chemical reduction of the biotransformation products yielded a tertiary alcohol identified as 2(R)-Isopropenyl-8(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.
KW - (+)-Valencene hydroperoxide
KW - Nootkatone
KW - Pleurotus sapidus
KW - Valencene dioxygenase
UR - http://www.scopus.com/inward/record.url?scp=70349414278&partnerID=8YFLogxK
U2 - 10.1016/j.biortech.2009.08.087
DO - 10.1016/j.biortech.2009.08.087
M3 - Article
C2 - 19765983
AN - SCOPUS:70349414278
VL - 101
SP - 457
EP - 462
JO - Bioresource technology
JF - Bioresource technology
SN - 0960-8524
IS - 2
ER -