Chiral gas chromatography for the determination of 1,2-O-isopropylidene-sn-glycerol stereoisomers

A stereospecific gas chromatography (GC) method using a (6-O-tButyldimethylsilyl-2,3-di-O-methyl)-beta-cyclodextrin as the chiral stationary phase has been developed and validated for the determination of the enantiomers of 1,2-O-isopropylidene-sn-glycerol (IPG), an important chiral synthon, in kinetic resolution experiments. After liquid-liquid extraction with ethyl acetate, the enantiomers of R-(-)-IPG and S-(+)-IPG and their corresponding butyrate- and caprylate esters were baseline separated using this chiral GC method. The method was accurate, reproducible, specific, and precise and recoveries of at least 77% were accomplished. The detection limits for IPG and its esters were 0.6 ng and 0.1 ng, respectively. The application of this method was demonstrated by a kinetic resolution experiment using the lipase A of Bacillus subtilis.