(S)-2-hydroxypropyl-beta-cyclodextrin, a new chiral stationary phase for reversed-phase liquid chromatography

(S)-2- and (R,S)-2-hydroxypropyl-beta-cyclodextrin have been bonded to silica gel and evaluated as stationary phases for reversed-phase liquid chromatography. Stationary phases also were prepared on two silicas having different pore sizes and surface areas. Dissimilarities were observed in enantiomeric selectivities between these columns and also between these and the native beta-cyclodextrin columns. With the exception of compounds 5 and 10, all other racemates reported here which have been successfully resolved on the new phases are enantiomers which have not been previously reported as separated on the beta-cyclodextrin stationary phase. In some cases, there were also differences in enantioselectivities observed between the (S)- and the (R,S)-hydroxypropyl-beta-cyclodextrin phases on the same silica. The results are discussed in terms of the retention mechanism and compared to results reported earlier for beta-cyclodextrin columns.