Gollamudi R, Feng Z X
Department of Medicinal Chemistry, College of Pharmacy, University of Tennessee-Memphis 38163.
Chirality. 1991;3(6):480-3. doi: 10.1002/chir.530030613.
alpha,alpha'-Bis[3-(N,N-diethylcarbamoyl)piperidino]-p-xylene dihydrobromide, a novel antiplatelet agent, was resolved into three isomers A, B, and C, on a chiral alpha 1-acid glycoprotein analytical column using a mobile phase of 0.025 M phosphate buffer containing 0.025 M tetrabutylammonium hydrogen sulfate, at a pH of 6.5. The effect of molarity, temperature, pH, flow rate, and organic modifiers on the enantioselectivity was examined. Based on circular dichroic spectra at 220 nm, A and C appear to be the (-)- and (+)-enantiomers, respectively, and B the meso diastereomer. Attempts at resolution using Pirkle type columns gave unsatisfactory results. It appears that both hydrophobic and polar interactions between the compound and the stationary phase are important determinants of resolution.
新型抗血小板药物α,α'-双[3-(N,N-二乙基氨基甲酰基)哌啶基]-对二甲苯二氢溴化物在含有0.025 M硫酸氢四丁铵的0.025 M磷酸盐缓冲液（pH 6.5）流动相的手性α1-酸性糖蛋白分析柱上被拆分为三种异构体A、B和C。研究了摩尔浓度、温度、pH、流速和有机改性剂对 enantioselectivity 的影响。基于220 nm处的圆二色光谱，A和C似乎分别是(-)-和(+)-对映体，B是内消旋非对映体。使用Pirkle型柱进行拆分的尝试得到了不理想的结果。看来化合物与固定相之间的疏水和极性相互作用都是拆分的重要决定因素。
