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Mechanistic aspects of the biogenesis of rose oxide in Pelargonium graveolens L'Héritier
Author(s) -
Wüst Matthias,
Rexroth Annette,
Beck Thomas,
Mosandl Armin
Publication year - 1998
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/(sici)1520-636x(1998)10:3<229::aid-chir5>3.0.co;2-4
Subject(s) - chemistry , citronellol , photooxygenation , chirality (physics) , biogenesis , singlet oxygen , terpene , essential oil , stereochemistry , organic chemistry , chromatography , oxygen , geraniol , biochemistry , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , gene , quark
Mechanistic aspects of the biogenesis of the chiral monoterpenoid rose oxide in Pelargonium graveolens L'Héritier are investigated using deuterium‐labelled precursors. After administration of the precursors using the cut‐stem method, the dynamic headspace extracts of the plants are analysed using multidimensional gas chromatography‐mass spectrometry (enantio‐MDGC‐MS). It is unequivocally shown that this plant is able to convert citronellol and menthocitronellol into cis‐/trans ‐rose oxide. Menthocitronellol is converted into rose oxide with a clearly detectable enantiodiscrimination. These facts may be explained with the presence of an oxidase, which is able to oxidize citronellol and menthocitronellol in allylic position. A photooxygenation mechanism including singlet oxygen as the oxidizing agent is rather unlikely. Chirality 10:229 – 237, 1998 . © 1998 Wiley‐Liss, Inc.