吡啶二甲酰胺基桥联双β-环糊精手性固定相的制备和评价

钟慧 曾庆丽 张天赐 双亚洲 李来生

引用本文: 钟慧, 曾庆丽, 张天赐, 双亚洲, 李来生. 吡啶二甲酰胺基桥联双β-环糊精手性固定相的制备和评价[J]. 分析化学, 2022, 50(3): 433-444. doi: 10.19756/j.issn.0253-3820.210787 shu
Citation:  ZHONG Hui,  ZENG Qing-Li,  ZHANG Tian-Ci,  SHUANG Ya-Zhou,  LI Lai-Sheng. Preparation and Evaluation of a Pyridinediamide Bridged Bis(β-cyclodextrin) Chiral Stationary Phase[J]. Chinese Journal of Analytical Chemistry, 2022, 50(3): 433-444. doi: 10.19756/j.issn.0253-3820.210787 shu

吡啶二甲酰胺基桥联双β-环糊精手性固定相的制备和评价

    通讯作者: 李来生,E-mail:lilaishengcn@163.com
  • 基金项目:

    国家自然科学基金项目(Nos.31860469,21165012)和江西省科技创新平台项目(No.20192BCD40001)资助。

摘要: 基于吡啶-2,3-二甲酸和6-氨基-β-环糊精的缩合反应,合成了桥联β-环糊精,将其键合到硅胶表面,制备了一种新型的吡啶二甲酰胺基桥联双β-环糊精手性固定相(PyCDP)。以黄烷酮类、三唑类、氨基酸类、β-受体阻滞剂类共38种手性药物和农药作探针,系统评价了此固定相的手性色谱性能,并采用自制的天然环糊精固定相(CDCSP)作为对比。结果表明,PyCDP可在反相和极性有机两种模式下拆分全部38种手性物质,其中2'-羟基黄烷酮、粉唑醇、苯丙氨酸和艾司洛尔对映体的分离度(Rs)分别为2.36、1.98、1.86和1.62,分析时间较短(<30 min)。反相色谱模式下,PyCDP可在15~30℃温度范围通过调节流动相中乙腈体积分数(20%~35%)实现三唑类农药的基线分离,并能将含两个手性中心的三唑醇和联苯三唑醇分别拆分为4个峰。在流动相pH 5.0~6.5范围内,PyCDP可基线拆分易电离的酸性、碱性和极性氨基酸对映体。此外,PyCDP也适用于极性有机模式,如较大位阻的卡维地洛也能被拆分(Rs=1.42),并首次实现了贝凡洛尔在环糊精类固定相上的拆分。而CDCSP只能拆分其中的20种手性物质,且分离度偏低。PyCDP结构中,桥联环糊精上邻近的两个空腔的协同包结作用和吡啶二甲酰胺桥基提供氢键、π-π作用有助于手性分离。研究结果表明,PyCDP是一种多功能的手性分离材料。

English


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  • 收稿日期:  2021-10-12
  • 修回日期:  2021-12-07
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