Details
| Originalsprache | Englisch |
|---|---|
| Seiten (von - bis) | 4333-4339 |
| Seitenumfang | 7 |
| Fachzeitschrift | Journal of Agricultural and Food Chemistry |
| Jahrgang | 56 |
| Ausgabenummer | 12 |
| Publikationsstatus | Veröffentlicht - 24 Mai 2008 |
Abstract
Lyophilisates of the ascomycetes Penicillium solitum and Aspergillus niger converted α-farnesene to 7-hydroxyfarnesene as the major product. The radical mechanism of this bioconversion was proven by electron spin resonance (ESR) and GC-MS using the spin trapping technique. Intermediate carbon-centered radicals of α-farnesene were captured using two spin traps, 2-methyl-2-nitrosopropane and α-(4-pyridyl-1-oxide)-N-tert-butylnitrone, respectively. The evaluation of the coupling constants and hyperfine couplings of the ESR spectra showed that tertiary carbon radicals were trapped. The radical position at C7 of α-farnesene was derived from El and Cl mass spectra of the corresponding MNP spin adduct. The present study demonstrates that the complementary application of ESR and MS spectrometric data allows the detailed evaluation of a radical mechanism of a fungal terpene transformation reaction.
ASJC Scopus Sachgebiete
- Chemie (insg.)
- Allgemeine Chemie
- Agrar- und Biowissenschaften (insg.)
- Allgemeine Agrar- und Biowissenschaften
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in: Journal of Agricultural and Food Chemistry, Jahrgang 56, Nr. 12, 24.05.2008, S. 4333-4339.
Publikation: Beitrag in Fachzeitschrift › Artikel › Forschung › Peer-Review
}
TY - JOUR
T1 - In vivo ESR spin trapping detection of carbon-centered α-farnesene radicals
AU - Krings, Ulrich
AU - Andersen, Mogens L.
AU - Berger, Ralf G.
PY - 2008/5/24
Y1 - 2008/5/24
N2 - Lyophilisates of the ascomycetes Penicillium solitum and Aspergillus niger converted α-farnesene to 7-hydroxyfarnesene as the major product. The radical mechanism of this bioconversion was proven by electron spin resonance (ESR) and GC-MS using the spin trapping technique. Intermediate carbon-centered radicals of α-farnesene were captured using two spin traps, 2-methyl-2-nitrosopropane and α-(4-pyridyl-1-oxide)-N-tert-butylnitrone, respectively. The evaluation of the coupling constants and hyperfine couplings of the ESR spectra showed that tertiary carbon radicals were trapped. The radical position at C7 of α-farnesene was derived from El and Cl mass spectra of the corresponding MNP spin adduct. The present study demonstrates that the complementary application of ESR and MS spectrometric data allows the detailed evaluation of a radical mechanism of a fungal terpene transformation reaction.
AB - Lyophilisates of the ascomycetes Penicillium solitum and Aspergillus niger converted α-farnesene to 7-hydroxyfarnesene as the major product. The radical mechanism of this bioconversion was proven by electron spin resonance (ESR) and GC-MS using the spin trapping technique. Intermediate carbon-centered radicals of α-farnesene were captured using two spin traps, 2-methyl-2-nitrosopropane and α-(4-pyridyl-1-oxide)-N-tert-butylnitrone, respectively. The evaluation of the coupling constants and hyperfine couplings of the ESR spectra showed that tertiary carbon radicals were trapped. The radical position at C7 of α-farnesene was derived from El and Cl mass spectra of the corresponding MNP spin adduct. The present study demonstrates that the complementary application of ESR and MS spectrometric data allows the detailed evaluation of a radical mechanism of a fungal terpene transformation reaction.
KW - α-farnesene
KW - Carbon-centered radicals
KW - ESR
KW - Free radicals
KW - Spin trapping
UR - http://www.scopus.com/inward/record.url?scp=47349085400&partnerID=8YFLogxK
U2 - 10.1021/jf800285n
DO - 10.1021/jf800285n
M3 - Article
C2 - 18500815
AN - SCOPUS:47349085400
VL - 56
SP - 4333
EP - 4339
JO - Journal of Agricultural and Food Chemistry
JF - Journal of Agricultural and Food Chemistry
SN - 0021-8561
IS - 12
ER -