Details
| Original language | English |
|---|---|
| Pages (from-to) | 329-335 |
| Number of pages | 7 |
| Journal | Journal of biotechnology |
| Volume | 159 |
| Issue number | 4 |
| Publication status | Published - 23 Jun 2011 |
Abstract
Mycelium of the basidiomycete Pleurotus sapidus known to contain a novel dioxygenase was used for the bioconversion of car-3-ene [I]. After 4h of incubation 25.3mgL-1 car-3-en-5-one [V], 5.4mgL-1 car-3-en-2-one [VII], and 7.3mgL-1 car-2-en-4-one [XV] accumulated as major oxidation products. The identity of the respective carenones and their corresponding alcohols was confirmed by comparison with MS and NMR spectral data obtained for synthesized authentic compounds. The peak areas of oxidation products were at least five times higher as compared with autoxidation. A radical mechanism similar to lipoxygenase catalysis was proposed and substantiated with detailed product analyses. The reduction of assumed car-3-ene hydroperoxides to the corresponding alcohols evidenced the radical initiated formation of hydroperoxides and confirmed the regio- and stereo-selectivity of the dioxygenase. The introduction of molecular oxygen into the bicyclic car-3-ene [I] molecule occurred at allylic positions of a cyclic isopentenyl moiety with a pronounced preference for the position adjacent to the non-substituted carbon atom of the C-C-double bond. This co-factor independent selective oxygenation presents an alternative to P450 mono-oxygenase based approaches for the production of terpene derived flavor compounds, pharmaceuticals and other fine chemicals.
Keywords
- (+)-Car-3-ene, Bioconversion, Dioxygenase, Pleurotus sapidus, Regio-selectivity, Stereo-selectivity
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biotechnology
- Chemical Engineering(all)
- Bioengineering
- Immunology and Microbiology(all)
- Applied Microbiology and Biotechnology
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In: Journal of biotechnology, Vol. 159, No. 4, 23.06.2011, p. 329-335.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Bioconversion of car-3-ene by a dioxygenase of Pleurotus sapidus
AU - Lehnert, Nicole
AU - Krings, Ulrich
AU - Sydes, Daniel
AU - Wittig, Maximilian
AU - Berger, Ralf G.
N1 - Funding information: Supported by Forschungskreis der Ernährungsindustrie e.V. (Bonn) through AIF and BMWi (AIF 299 ZN). H. Zorn and M.A. Fraatz are thanked for their kind cooperation.
PY - 2011/6/23
Y1 - 2011/6/23
N2 - Mycelium of the basidiomycete Pleurotus sapidus known to contain a novel dioxygenase was used for the bioconversion of car-3-ene [I]. After 4h of incubation 25.3mgL-1 car-3-en-5-one [V], 5.4mgL-1 car-3-en-2-one [VII], and 7.3mgL-1 car-2-en-4-one [XV] accumulated as major oxidation products. The identity of the respective carenones and their corresponding alcohols was confirmed by comparison with MS and NMR spectral data obtained for synthesized authentic compounds. The peak areas of oxidation products were at least five times higher as compared with autoxidation. A radical mechanism similar to lipoxygenase catalysis was proposed and substantiated with detailed product analyses. The reduction of assumed car-3-ene hydroperoxides to the corresponding alcohols evidenced the radical initiated formation of hydroperoxides and confirmed the regio- and stereo-selectivity of the dioxygenase. The introduction of molecular oxygen into the bicyclic car-3-ene [I] molecule occurred at allylic positions of a cyclic isopentenyl moiety with a pronounced preference for the position adjacent to the non-substituted carbon atom of the C-C-double bond. This co-factor independent selective oxygenation presents an alternative to P450 mono-oxygenase based approaches for the production of terpene derived flavor compounds, pharmaceuticals and other fine chemicals.
AB - Mycelium of the basidiomycete Pleurotus sapidus known to contain a novel dioxygenase was used for the bioconversion of car-3-ene [I]. After 4h of incubation 25.3mgL-1 car-3-en-5-one [V], 5.4mgL-1 car-3-en-2-one [VII], and 7.3mgL-1 car-2-en-4-one [XV] accumulated as major oxidation products. The identity of the respective carenones and their corresponding alcohols was confirmed by comparison with MS and NMR spectral data obtained for synthesized authentic compounds. The peak areas of oxidation products were at least five times higher as compared with autoxidation. A radical mechanism similar to lipoxygenase catalysis was proposed and substantiated with detailed product analyses. The reduction of assumed car-3-ene hydroperoxides to the corresponding alcohols evidenced the radical initiated formation of hydroperoxides and confirmed the regio- and stereo-selectivity of the dioxygenase. The introduction of molecular oxygen into the bicyclic car-3-ene [I] molecule occurred at allylic positions of a cyclic isopentenyl moiety with a pronounced preference for the position adjacent to the non-substituted carbon atom of the C-C-double bond. This co-factor independent selective oxygenation presents an alternative to P450 mono-oxygenase based approaches for the production of terpene derived flavor compounds, pharmaceuticals and other fine chemicals.
KW - (+)-Car-3-ene
KW - Bioconversion
KW - Dioxygenase
KW - Pleurotus sapidus
KW - Regio-selectivity
KW - Stereo-selectivity
UR - http://www.scopus.com/inward/record.url?scp=84861235510&partnerID=8YFLogxK
U2 - 10.1016/j.jbiotec.2011.06.007
DO - 10.1016/j.jbiotec.2011.06.007
M3 - Article
C2 - 21723336
AN - SCOPUS:84861235510
VL - 159
SP - 329
EP - 335
JO - Journal of biotechnology
JF - Journal of biotechnology
SN - 0168-1656
IS - 4
ER -