Yang S K, Mushtaq M, Bao Z P, Weems H B, Shou M G, Lu X L
Department of Pharmacology, F. Edward Hébert School of Medicine, Uniformed Services University of the Health Sciences, Bethesda, MD 20814-4799.
J Chromatogr. 1989 Jan 6;461:377-95. doi: 10.1016/s0021-9673(00)94305-x.
K-region trans-dihydrodiol derivatives of phenanthrene, 1-methylphenanthrene, 4,5-methylenephenanthrene, pyrene, 1-bromopyrene, chrysene, benzo[c]phenanthrene, benz[a]anthracene, 1-, 4-, 6-, 7-, 11- and 12-methylbenz[a]anthracenes, 7,12-dimethylbenz[a]anthracene, 3-methylcholanthrene, and benzo[a]pyrene, and non-K-region trans-3,4-dihydrodiols of benz[a]anthracene, chrysene, and 7,12-dimethylbenz[a]anthracene are converted to O-methyl ethers. Enantiomers of these O-methyl ethers are generally more efficiently separated on Pirkle's chiral stationary phases than the enantiomers of underivatized dihydrodiols. O-Methyl ethers are substantially less polar than dihydrodiols, and O-methyl ethers are eluted with shorter retention times. Eluents of lower polarity can hence be used. This enhances chiral interactions between chiral stationary phase and solutes, allowing improved separation of enantiomers.
菲、1-甲基菲、4,5-亚甲基菲、芘、1-溴芘、屈、苯并[c]菲、苯并[a]蒽、1-、4-、6-、7-、11-和12-甲基苯并[a]蒽、7,12-二甲基苯并[a]蒽、3-甲基胆蒽和苯并[a]芘的K-区域反式二氢二醇衍生物，以及苯并[a]蒽、屈和7,12-二甲基苯并[a]蒽的非K-区域反式3,4-二氢二醇被转化为O-甲基醚。这些O-甲基醚的对映体通常比未衍生化二氢二醇的对映体在Pirkle手性固定相上更有效地分离。O-甲基醚的极性比二氢二醇小得多，且O-甲基醚以较短的保留时间被洗脱。因此可以使用极性较低的洗脱剂。这增强了手性固定相与溶质之间的手性相互作用，从而改善了对映体的分离。
