The enantioselective separation of newly prepared, pharmacologically significant isopulegol-based ß-amino lactones and ß-amino amides has been studied by carrying out high-performance liquid chromatography on diverse amylose and cellulose tris-(phenylcarbamate)-based chiral stationary phases (CSPs) in n-hexane/alcohol/diethylamine or n-heptane/alcohol/ diethylamine mobile phase systems. For the elucidation of mechanistic details of the chiral recognition, seven polysaccharide-based CSPs were employed under normal-phase conditions. The effect of the nature of selector backbone (amylose or cellulose) and the position of substituents of the tris-(phenylcarbamate) moiety was evaluated. Due to the complex structure and solvation state of polysaccharide-based selectors and the resulting enantioselective interaction sites, the chromatographic conditions (e.g., the nature and content of alcohol modifier) were found to exert a strong influence on the chiral recognition process, resulting in a particular elution order of the resolved enantiomers. Since no prediction can be made for the observed enantiomeric resolution, special attention has been paid to the identification of the elution sequences. The comparison between the effectiveness of covalently immobilized and coated polysaccharide phases allows the conclusion that, in several cases, the application of coated phases can be more advantageous. However, in general, the immobilized phases may be preferred due to their increased robustness. Thermodynamic parameters derived from the temperature-dependence of the selectivity revealed enthalpically-driven separations in most cases, but unusual temperature behavior was also observed.

中文翻译：

---

在多糖类手性固定相上基于异薄荷醇的ß-氨基内酯和ß-氨基酰胺类似物的高效液相色谱对映体分离，重点在于对映体洗脱顺序的变化。

通过在各种直链淀粉和纤维素三（苯基氨基甲酸酯）基手性固定相（CSP）上进行高效液相色谱研究了新制备的，具有药理学意义的基于异薄荷醇的ß-氨基内酯和ß-氨基酰胺的对映选择性分离在正己烷/醇/二乙胺或正庚烷/醇/二乙胺流动相系统中 为了阐明手性识别的机理细节，在正相条件下使用了七种基于多糖的CSP。评价了选择主链（直链淀粉或纤维素）的性质和三-（苯基氨基甲酸酯）部分的取代基位置的影响。由于多糖基选择剂的复杂结构和溶剂化状态以及由此产生的对映选择性相互作用位点，发现色谱条件（例如，醇改性剂的性质和含量）对手性识别过程有很大影响，从而导致拆分的对映异构体具有特定的洗脱顺序。由于无法预测观察到的对映体分辨率，因此特别注意了洗脱序列的鉴定。共价固定的和包被的多糖相的有效性之间的比较可以得出这样的结论：在某些情况下，包被的相的应用可能更有利。然而，一般而言，固定相由于其增加的坚固性而可能是优选的。在大多数情况下，由选择性的温度依赖性得出的热力学参数显示出由焓驱动的分离，