title: Salient features of enantioselective gas chromatography: the enantiomeric differentiation of chiral inhalation anesthetics as a representative methodological case in point.
abstract: The enantiomeric differentiation of the volatile chiral inhalation anesthetics enflurane, isoflurane, and desflurane by analytical and preparative gas chromatography on various modified cyclodextrins is described. Very large enantioseparation factors α are obtained on the chiral selector octakis(3-O-butanoyl-2,6-di-O-pentyl)-γ-cyclodextrin (Lipodex E). The gas-chromatographically observed enantioselectivities are corroborated by NMR-spectroscopy using Lipodex E as chiral solvating agent and by various sensor devices using Lipodex E as sensitive chiral coating layer. The assignment of the absolute configuration of desflurane is clarified. Methods are described for the determination of the enantiomeric distribution of chiral inhalation anesthetics during narcosis in clinical trials. The quantitation of enantiomers in a sample by the method of enantiomeric labeling is outlined. Reliable thermodynamic parameters of enantioselectivity are determined by using the retention-increment R' approach for the enantiomeric differentiation of various chiral halocarbon selectands on diluted cyclodextrin selectors.
authors.affiliation: Institute of Organic Chemistry, University of Tübingen, Auf der Morgenstelle 18, 72076, Tübingen, Germany, volker.schurig@uni-tuebingen.de.
authors.forename: Volker
authors.initials: V
authors.lastname: Schurig
mesh_terms: D000769:Anesthesia, Inhalation / Q000379:methods; D018685:Anesthetics, Inhalation / Q000737:chemistry / Q000302:isolation & purification*; D002849:Chromatography, Gas / Q000295:instrumentation / Q000379:methods*; D000077335:Desflurane; D004737:Enflurane / Q000737:chemistry / Q000302:isolation & purification; D006801:Humans; D007530:Isoflurane / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism; D013816:Thermodynamics; D047408:gamma-Cyclodextrins / Q000737:chemistry
chemical_list: D018685:Anesthetics, Inhalation; D047408:gamma-Cyclodextrins; C113626:octakis(3-O-butanoyl-2,6-di-O-pentyl)cyclodextrin; D004737:Enflurane; D000077335:Desflurane; D007530:Isoflurane; C023792:gamma-cyclodextrin