色谱

色谱 ›› 2016, Vol. 34 ›› Issue (1): 74-79.DOI: 10.3724/SP.J.1123.2015.10036

• 研究论文 • 上一篇    下一篇

键合型聚丙烯酰胺衍生物手性固定相的制备与手性识别性能

宋佳枫1, 冯四伟1, 徐晓冬1, 刘立佳1, 宋超坤1, 温晓琨1, 陈进勇1, 李芳坤1, 冈本佳男1,2   

  1. 1. 哈尔滨工程大学材料科学与化学工程学院, 黑龙江 哈尔滨 150001;
    2. 日本名古屋大学, 日本 名古屋 464-8603
  • 收稿日期:2015-10-26 出版日期:2016-01-08 发布日期:2012-08-01
  • 通讯作者: 徐晓冬
  • 基金资助:

    国家自然科学基金项目(51103030);黑龙江省自然科学基金项目(E201419);哈尔滨市科技创新人才研究专项(2013RFLXJ027);日本大赛璐公司合作研究基金.

Preparation and chiral recognition ability of chiral stationary phase based on immobilized polyacrylamide derivative

SONG Jiafeng1, FENG Siwei1, XU Xiaodong1, LIU Lijia1, SONG Chaokun1, WEN Xiaokun1, CHEN Jinyong1, LI Fangkun1, OKAMOTO Yoshio1,2   

  1. 1. College of Materials Science and Chemical Engineering, Harbin Engineering University, Harbin 150001, China;
    2. Nagoya University, Nagoya 464-8603, Japan
  • Received:2015-10-26 Online:2016-01-08 Published:2012-08-01
  • Supported by:

    National Natural Science Foundation of China (No. 51103030); Natural Science Foundation of Heilongjiang Province of China (No. E201419); Harbin City Scientific and Technological Innovation Talent Fund of China (No. 2013RFLXJ027); Collaborative Research Fund of Daicel Corporation (Tokyo, Japan).

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被引次数

5

摘要：

高效液相色谱(HPLC)被广泛认为是分离制备光学纯单一对映体的最有效方法。在高效液相色谱手性拆分中,手性固定相(CSP)的性能直接影响到色谱柱的手性分离能力。在众多手性固定相中,键合型手性固定相具有溶剂耐受性好,分离模式灵活等优点,已经发展成为一类重要的手性固定相。本文通过两步化学反应合成了新型的光学活性丙烯酰胺衍生物——(S)-1-丙烯酰-2-(N-苯基甲酰胺基)吡咯烷((S)-APACP),采用核磁共振氢谱表征了(S)-APACP的化学结构;通过3步化学反应制备了键合型聚丙烯酰胺衍生物手性固定相,采用热重分析法表征了聚合物的键合量,采用HPLC评价了键合型手性固定相的识别能力,分析了影响其手性识别能力的因素。研究结果表明,APACP聚合物成功地键合到硅胶表面制备了具有良好溶剂耐受性的键合型手性固定相,其聚合物键合量为10.2%~11.8%,该键合型手性固定相对若干种对映体显示了较好的手性识别能力。

关键词: 高效液相色谱, 聚丙烯酰胺衍生物, 手性固定相, 手性识别能力

Abstract:

High performance liquid chromatography (HPLC) has been widely considered as the most effective way for the separation and preparation of optically pure enantiomers. In the resolution by HPLC, the separation ability of a column strongly depends on the properties of a chiral stationary phase (CSP). Among many CSPs, the immobilized CSPs, which are becoming one of the most important kinds of CSPs, have the advantages of good solvent durability and enormous method flexibility. In this work, a novel optically active acrylamide derivative (S)-APACP was synthesized by two-step reactions, and its chemical structure was characterized by 1H NMR. The polyacrylamide derivatives were immobilized on silica gel by three-step reactions to prepare immobilized CSPs, and the immobilization amount of the polymers was tested by thermogravimetric analysis. The chiral recognition ability of the immobilized CSPs was evaluated by HPLC, and the effects of Lewis acid and mobile phase on the chiral recognition ability were investigated. The results showed that APACP polymer was successfully immobilized on silica gel to prepare immobilized-type CSP with better solvent durability, and the amount of immobilized polymer was 10.2% to 11.8%. The immobilized-type CSP showed good chiral recognition ability for several enantiomers.

Key words: chiral recognition ability, chiral stationary phases (CSP), high performance liquid chromatography (HPLC), polyacrylamide derivative

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