Orosz Tímea, Bajtai Attila, Minh Le Tam, Tanács Dániel, Szakonyi Zsolt, Fülöp Ferenc, Péter Antal, Ilisz István
Institute of Pharmaceutical Analysis, University of Szeged, Szeged, Hungary.
Institute of Pharmaceutical Chemistry and Research Group for Stereochemistry, Hungarian Academy of Sciences, University of Szeged, Szeged, Hungary.
Biomed Chromatogr. 2019 May;33(5):e4517. doi: 10.1002/bmc.4517. Epub 2019 Mar 13.
Enantioseparation of limonene-based bicyclic 1,3-aminoalcohols and 1,3,5- and 1,3,6-aminodiols was performed by normal-phase high-performance liquid chromatographic and supercritical fluid chromatographic (SFC) methods on polysaccharide-based chiral stationary phases. The effects of the composition of the mobile phase, the column temperature and the structures of the analytes and chiral selectors on retention and selectivity were investigated by normal-phase LC and SFC technique. Thermodynamic parameters derived from selectivity-temperature-dependence studies were found to be dependent on the chromatographic method applied, the nature of the chiral selector and the structural details of the analytes. Enantiorecognition in most cases was enthalpically driven but an unusual temperature behavior was also observed: decreased retention times were accompanied by improved separation factors with increasing temperature, i.e. some entropically driven separations were also observed. The elution sequence was determined in all cases. The separation of the stereoisomers was optimized in both chromatographic modalities.
基于多糖的手性固定相，采用正相高效液相色谱法和超临界流体色谱法（SFC）对柠檬烯基双环1,3 -氨基醇以及1,3,5 -和1,3,6 -氨基二醇进行了对映体拆分。通过正相液相色谱和SFC技术，研究了流动相组成、柱温以及分析物和手性选择剂的结构对保留和选择性的影响。从选择性-温度依赖性研究中得出的热力学参数被发现取决于所应用的色谱方法、手性选择剂的性质以及分析物的结构细节。在大多数情况下，对映体识别是由焓驱动的，但也观察到了异常的温度行为：随着温度升高，保留时间缩短，分离因子提高，即也观察到了一些由熵驱动的分离。在所有情况下都确定了洗脱顺序。在两种色谱模式下都对立体异构体的分离进行了优化。
