Preparation and application of urea-based derivatized β-cyclodextrin chiral stationary phase based on diazotized silica microspheres

Abstract

Recently, the design and development of efficient chiral stationary phases is still the core and goal of chiral chromatography. In order to quickly separate chiral drugs, we designed and prepared an environmentally friendly small particle chiral stationary phase: p-methylphenylurea-β-cyclodextrin chiral stationary phase (SiO2@PMPU-β-CD). Firstly, p-methylphenylurea-β-cyclodextrin (PMPU-β-CD) was connected to the surface of mesoporous silica microspheres by diazoresin (DR) to prepare a SiO2@PMPU-β-CD. In reverse elution mode, the column temperature was set at 25 °C, the flow rate was 0.2 mL/min, and ACNH2O (v/v = 70:30) was used as the elution condition of the mobile phase. The enantiomers of chlorpheniramine maleate, 2-phenylcyclohexanone, and promethazine were separated within 5 min. In addition, the addition of TEAA buffer to the mobile phase improved the enantiomer resolution of chlorpheniramine maleate from 1.03 to 5.69. The experimental results show that the SiO2@PMPU-β-CD column can be used for the separation of appellant chiral drugs with good repeatability, and the use of DR instead of silane coupling agent has the advantages of being non-toxic, environmentally protected, and easy to operate, which is of great significance for the development of chiral stationary phase.