Preparative enantiomer separation of the inhalation anesthetics enflurane, isoflurane and desflurane by gas chromatography on a derivatized gamma-cyclodextrin stationary phase.
The preparative enantiomeric separation of the inhalation anesthetics enflurane (1) and isoflurane (2) in very high chemical (> 99.5%) and enantiomeric excess (ee > 99%) by gas chromatography (GC) on octakis(3-O-butanoyl-2,6-di-O-n-pentyl)-gamma-cyclodextrin (4), dissolved in the apolar polysiloxane SE-54 and coated on Chromosorb P AW DMCS, is described. Up to 1 g of each enantiomer of 1-2 can been obtained per diem. The enantiomers of the highly volatile desflurane (3) can also be separated, albeit with diminished ee. The enantiomeric excess of 1-3 was checked by analytical GC on 4 and the absolute configuration of 2 and 3 has been determined via anomalous X-ray diffraction.
Juza
M
M
Institut für Organische Chemie, Universität Tübingen, Germany.
Braun
E
E
Schurig
V
V
D018685:Anesthetics, Inhalation / Q000737:chemistry / Q000302:isolation & purification*; D002849:Chromatography, Gas / Q000295:instrumentation / Q000379:methods; D003505:Cyclodextrins / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D000077335:Desflurane; D004737:Enflurane / Q000737:chemistry / Q000302:isolation & purification*; D007530:Isoflurane / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification*; D015394:Molecular Structure; D013237:Stereoisomerism
D018685:Anesthetics, Inhalation; D003505:Cyclodextrins; D004737:Enflurane; D000077335:Desflurane; D007530:Isoflurane