Chiral HPLC separation with self-assembled organic stationary phase

手性拆分仍然是分析化学和分离技术的重要目标，因为每种对映体在生物体系中的作用是完全不同的。手性固定相高效液相色谱法是一种简便的手性固定相方法。然而，很少有例子是通过反相-高效液相模式来完成的，因为这是最方便的高效液相色谱模式。这是因为每个对映体中没有疏水性差异。因此，我们着眼于自组装体系来增强分子识别中的微环境效应，并将其应用于功能有机固定相。我们的研究项目阐明：(1)聚丙烯酸十八酯接枝二氧化硅通过长链烷基部分的无序到有序的陈旧相变，对识别多环芳烃分子形状的微小差异显示出明显的增强选择性，(2)固定相与溶质之间的多个羰基-π相互作用导致了选择性的提高，以及(3)这种高效液相色谱与非对映聚合剂的结合显示了对生成的非对映异构体的增强的选择性。

Chiral separation is still significant target in analytical chemistry and separation technology because each enantiomer provides absolutely different action in biosystems. HPLC with chiral stationary phase has been recognized as a facile method to perform it. However, there are few examples those were accomplished with a reversed phase-HPLC mode as the most convenient HPLC. This is due to no hydrophobicity difference in each enantiomer. Therefore, we focused on self-assembled systems to enhance microenvironmental effect in molecular recognition and applied these systems for functional organic stationary phases. Our research project clarified that (1)poly(octadecyl acrylate)-grafted silica showed distinct enhanced selectivity to recognize small difference in the molecular shape of polyaromatic hydrocarbons through disordered-to-ordered stale phase transition of the long-chain alkyl moieties, (2)the enhanced selectivity was brought about from multiple carbonyl-π interaction between the stationary phase and solutes, and (3)combination of this HPLC with diastereomerizing agents showed enhanced selectivity for the resultant diastereomers.