Biogenetic studies in Mentha x piperita. 1. deuterium-labeled monoterpene ketones: synthesis and stereoselective analysis.
Pulegone, menthone, and isomenthone isotopomers are synthesized as regioselectively deuterated d(5)- and d(8)-stereoisomers. Deuterium-labeled menthone and isomenthone enantiomers are analyzed using enantioselective multidimensional gas chromatography/mass spectrometry. The deuterated stereoisomers of menthone and isomenthone are separated from the unlabeled menthone and isomenthone on a glass capillary column, coated with 50% octakis(2, 3-di-O-butyryl-6-O-tert- butyldimethylsilyl)-gamma-cyclodextrin in OV 1701vi as the chiral stationary phase. These deuterium-labeled monoterpene ketones are proved to be highly valuable substrates in biosynthetic studies of terpenoid compounds.
Fuchs
S
S
Institut für Lebensmittelchemie, Johann Wolfgang Goethe-Universität Frankfurt, Germany.
Beck
T
T
Burkardt
S
S
Sandvoss
M
M
Mosandl
A
A
D003903:Deuterium; D008401:Gas Chromatography-Mass Spectrometry; D007553:Isotope Labeling / Q000379:methods; D007659:Ketones / Q000737:chemistry / Q000378:metabolism*; D019686:Lamiaceae / Q000378:metabolism*; D019684:Magnoliopsida / Q000378:metabolism; D013729:Terpenes / Q000737:chemistry / Q000378:metabolism*
D007659:Ketones; D013729:Terpenes; D003903:Deuterium