新型衍生化β-环糊精键合硅胶手性固定相的合成与性能研究

Synthesis and Chromatographic Properties of a Novel Phenyl Carbamate Perderivatized β-Cyclodextrin Bonded Silica Chiral Stationary Phase

合成了苯基氨基甲酸酯全衍生化β-环糊精键合硅胶手性固定相.在正相色谱条件下,对系列2-(噻唑基)-α-氨基膦酸酯化合物进行了有效的手性拆分研究.结果表明,所有化合物都得到基线分离,对映异构体选择性α>1.2,为制备型液相色谱的手性拆分提供条件.

A novel chiral stationary phase has been prepared by immobilized of(mono-6-ethylene diamine-6-deoxy-2, 3, 6-perphenylcarbamated)β-cyclodextrin onto the surface of silica gel via the spacer 3-iso-cyanatopropyl-triethoxysilane with an extended application of the ester exchange reaction, in order to achieve the following two aims: firstly, we tried to use a facile method to get a characteristic multimode chiral stationary by adding more effective interaction sites ; secondly, we wanted to achieve the separation of chiral organophosphorus compounds. The resulting bonded silica stationary phase was characterized by the bonded density of derivative β-CD calculated from the results of C, H and N elemental analyses and spectrum analysis, etc.. The column performance was up to 48 000 plates/m, and symmetry factor up to 1. 095. A series of fifteen 2-(thiazolyl)-α-amidophosphonates organophosphorus compounds were successfully separated into their enantiomers in the normal phase of HPLC for the first time. Some of them could be separated in baseline, good enantioseparations with separation factors of a up to 1. 789. Strong π-π interaction or dipole-dipole interaction, hydrophobic interaction etc. , contribute to the possible chiral recognition mechanism.