Chromatographia ( IF 1.7 ) Pub Date : 2021-05-12 , DOI: 10.1007/s10337-021-04048-5 Helena Kažoka , Baiba Turovska , Toms Upmanis , Natalja Orlova , Maksims Vorona
Our previous studies concerning the enantioseparation of 4C-substituted pyrrolidin-2-one derivatives on coated polysaccharide-based chiral stationary phases have shown that amylose-based chiral selectors, together with mobile phases consisting of ethanol and n-hexane mixtures, are the most effective. To extend this research, five commercially available immobilized amylose-based chiral stationary phases (3,5-dimethylphenylcarbamate, 3-chlorophenylcarbamate, 3,5-dichlorophenylcarbamate, 3-chloro-4-methylphenylcarbamate and 3-chloro-5-methylphenylcarbamate) were tested with ethanol-containing mobile phases and obtained results were compared with data obtained on coated phases (3,5-dimethylphenylcarbamate and 5-chloro-2-methylphenylcarbamate). The effect of the nature of chiral stationary phase and analytes studied on enantiomer elution order, retention and resolution was tested. Compared to immobilized phase based on amylose 3,5-dimethylphenylcarbamate with its coated version, a better enantioseparation is observed on coated column. However, in addition to the coated amylose-based phases, immobilized phases with both methyl- and chloro-substituents in phenylcarbamate moiety were found to best separate the 4C-substituted pyrrolidin-2-one derivatives. Non-typical eluents with medium-polarity solvents were tested for the separation of three 4C-phenyl-substituted racemic compounds on five immobilized phases. Enantiorecognition of amylose derivatives containing 3,5-dimethylphenylcarbamate and 3-chloro-5-methylphenylcarbamate improved when working with mobile phases containing ethyl acetate, methyl tert-butyl ether and dichloromethane.
Graphical abstract
中文翻译:
基于直链淀粉的手性固定相上4C取代的Pyrrolidin-2-One衍生物的分离
我们先前关于在包衣的基于多糖的手性固定相上对映体拆分4C取代的吡咯烷-2-酮衍生物的研究表明,基于直链淀粉的手性选择剂,以及由乙醇和正丙醇组成的流动相-己烷混合物是最有效的。为了扩展这项研究,测试了五个市售的固定化直链淀粉基手性固定相(3,5-二甲基苯基氨基甲酸酯,3-氯苯基氨基甲酸酯,3,5-二氯苯基氨基甲酸酯,3-氯-4-甲基苯基氨基甲酸酯和3-氯-5-甲基苯基氨基甲酸酯)。用含乙醇的流动相进行分析,并将所得结果与包被相(3,5-二甲基苯基氨基甲酸酯和5-氯-2-甲基苯基氨基甲酸酯)获得的数据进行比较。测试了手性固定相和分析物的性质对对映体洗脱顺序,保留度和分离度的影响。与基于带涂层的直链淀粉3,5-二甲基苯基氨基甲酸酯的固定相相比,在带涂层的色谱柱上观察到更好的对映体分离。但是,除了包被的直链淀粉相之外,发现在苯基氨基甲酸酯部分中同时具有甲基和氯取代基的固定相可以最好地分离4C取代的吡咯烷-2-一衍生物。测试了使用中极性溶剂的非典型洗脱液在五个固定相上分离三种4C-苯基取代的外消旋化合物的方法。与含有乙酸乙酯,甲基丙烯酸的流动相一起使用时,含有3,5-二甲基苯基氨基甲酸酯和3-氯-5-甲基苯基氨基甲酸酯的直链淀粉衍生物的对映异构体识别得到改善叔丁基醚和二氯甲烷。