Chiral Phase High-Performance Liquid Chromatographic Separation of Enantiomeric 1, 2-and 2, 3-O-Isopropylidene-snglycerols as 3, 5-Dinitrophenylurethanes

概要

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High-performance liquid chromatographic separation of enantiomeric 1,2- and 2,3-O-isopropylidene-sn-glycerols was performed on two different stationary phases of opposite configurations: N-(S)-1-(α-naphthyl)ethylaminocarbonyl-(S)-tert-leucine and N-(R)-1-(α-naphthyl)ethylaminocarbonyl-(R)-tert-leucine. This caused a reversal in the order of enantiomer elution. The isopropylideneglycerols were chromatographed as 3,5-dinitrophenylurethane derivatives. Complete enantiomer resolution, which permitted an accurate estimation of the optical purity of each enantiomer, was easily achieved on both columns (each 25 cm × 4.6 mm i.d.) within 15 min after an injection by an isocratic elution with hexane/dichloromethane/ethanol (40:12:3, by vol) as the mobile phase. The formations of diastereomeric π-π donor-accepter interaction, hydrogen bonding association, and dipole-dipole stacking between the solutes and the chiral stationary phases were considered as contributing factors to enantiomer resolution. Under optimal conditions, the optical purities of several commercially available 1,2-O-isopropylideneglycerol enantiomers were successfully determined in this study. The new method used in this study demonstrates that chiral phase high-performance liquid chromatography provides effective resolution, identification, and quantitation of synthetic 1,2- and 2,3-O-isopropylidene-sn-glycerol enantiomers.
日本油化学会の論文
2004-08-01