Semipreparative-scale gas-chromatographic separation of filbertone enantiomers.
The enantioselectivity of heptakis(2,3-di-O-acetyl-6-O-tert-butyldimethylsilyl-beta-CD) toward racemic filbertone (E-5-methyl-hep-2-en-4-one) was studied by performing the chiral separation on a capillary column, a thick-film wide-bore column and a semipreparative column. The semipreparative enantioseparation of filbertone was achieved at 80 degrees C by using a packed column providing (R)- and (S)-enantiomers of filbertone with ee 90 and 96%, respectively. The isolated enantiomers (approximately 250 microg each, ee = 90-96%) may be used for studies on the relationship of chirality and biological activity by olfactory screening and toxicological studies.
Blanch
Gracia Patricia
GP
Instituto de Fermentaciones Industriales, Consejo Superior Investigaciones Cientificas (CSIC), c/ Juan de la Cierva 3, Madrid, Spain. gblanch@ifi.csic.es
Ruiz del Castillo
Marisa L
ML
D002849:Chromatography, Gas / Q000379:methods*; D006536:Heptanes / Q000032:analysis / Q000302:isolation & purification; D010938:Plant Oils / Q000737:chemistry; D013237:Stereoisomerism
D006536:Heptanes; D010938:Plant Oils; C475234:5-methylhept-2-en-4-one