双选择体手性固定相中选择体的构型对分离性能的影响

为研究选择体的构型对双选择体固定相手性识别的影响,以(1S,2S)-(~)-二苯基乙二胺及L-(~)-二苯甲酰酒石酸为手性源,合成了一种新的双选择体固定相,并用不同结构的手性样品测试了其手性分离能力。结果表明,这种固定相与以(1R,2R)-(+)-二苯基乙二胺及L(~)-二苯甲酰酒石酸为手性源制备的双选择体固定相有相当的手性分离能力,但这两种固定相所能分离的化合物不尽相同。对双选择体固定相中两个选择体的构型对固定相手性识别的影响进行了探讨。在手性识别中,以不同手性源制备的两个选择体的立体构型不能同时与一个手性样品的立体构型相匹配,从而导致相应的双选择体固定相手性分离能力的下降。

Influence of selector configurations of biselector chiral stationary phases on enantioseparation

In order to investigate the influence of selector configurations of a biselector chiral stationary phase (CSP) on its chiral recognition, a new biselector CSP was prepared in this work using (1S,2S)-(~)-1,2-diphenylethylenediamine (DPEDA) and L-(~)-dibenzoyl tartaric acid (DBTA) as the chiral origins. The enantioseparation ability of the biselector CSP was evaluated towards chiral analytes of different structures under normal, polar organic and reverse phase modes. The chromatographic separation results showed that the enantioseparation ability of the CSP was equivalent to that of another biselector CSP in previous work, which was derived from (1R,2R)-(+)-1,2-DPEDA and L-(~)-DBTA. However, the chiral compounds separated on the two CSPs were not identical. The influence of selector configurations of biselector CSPs on the chiral recognition was discussed. In the event that the two selectors in a biselector CSP were prepared from different chiral compounds, the stereo-configurations of the two selectors cannot simultaneously match the ones of a chiral analyte, thus causing the decrease in the enantioseparation ability of the biselector CSP.