Abstract

A novel chiral selector polyacrylic acid-β-cyclodextrin (PAA-β-CD) was successfully prepared, then a facile synthesis of PAA-β-CD stationary phase based on diazotized silica was developed and characterized. Monodisperse silica microspheres were synthesized by a modified Stöber method. The obtained silica particles were functionalized by self-assembly positive charged photosensitive diazoresin (DR) and PAA-β-CD on the surface. The corresponding chiral stationary phase (CSP) was used in HPLC and the enantioseparation performance was investigated in both polar organic and reverse phase mode. Better separation abilities and excellent enantio-selectivities were obtained on PAA-β-CD CSP for antihistamine drugs in the acetonitrile and triethylammonium acetate buffer mobile phase.

Abbreviations: AIBN: azodiisobutyronitrile; β-CD: b-cyclodextrin; β-CD-NH2: amino-β-CDcyclodextrin; β-CD-OTs: sulfonyl-b-cyclodextrin; CD: cyclodextrin; CSP: chiral stationary phase; DCC: dicyclohexyl carbimide; DR: diazoresin; MeOH: methanol; NMP: N-methyl pyrrolidone; PAA: polyacrylic acid; PAA-β-CD: polyacrylic acid-β-cyclodextrin; TEAA: triethylammonium acetate; TEOS: tetraethyl orthosilicate

摘要

成功制备了一种新型手性选择剂聚丙烯酸-β-环糊精（PAA-β-CD），然后开发并表征了一种基于重氮化硅胶的PAA-β-CD固定相的简便合成方法。单分散二氧化硅微球是通过改进的 Stöber 方法合成的。获得的二氧化硅颗粒通过表面自组装带正电荷的光敏重氮树脂（DR）和 PAA-β-CD 进行功能化。相应的手性固定相 (CSP) 用于 HPLC，并在极性有机和反相模式下研究对映分离性能。PAA-β-CD CSP 在乙腈和醋酸三乙铵缓冲液流动相中对抗组胺药物具有更好的分离能力和优异的对映选择性。

缩写：AIBN：偶氮二异丁腈；β-CD：β-环糊精；β-CD-NH2：氨基-β-CD环糊精；β-CD-OTs：磺酰基-β-环糊精；CD：环糊精；CSP：手性固定相；DCC：二环己基碳酰亚胺；DR：重氮树脂；MeOH：甲醇；NMP：N-甲基吡咯烷酮；PAA：聚丙烯酸；PAA-β-CD：聚丙烯酸-β-环糊精；TEAA：三乙基醋酸铵；TEOS：原硅酸四乙酯