色谱

色谱 ›› 2014, Vol. 32 ›› Issue (5): 452-457.DOI: 10.3724/SP.J.1123.2014.01022

• 研究论文 • 上一篇    下一篇

新型键合纤维素手性固定相的制备及其拆分性能评价

涂鸿盛1, 范军1, 谭艺2, 林纯1, 华江颖1, 章伟光1,2   

  1. 1. 华南师范大学化学与环境学院, 广东 广州 510006;
    2. 广州研创生物技术发展有限公司, 广东 广州 510663
  • 收稿日期:2014-01-13 修回日期:2014-03-01 出版日期:2014-05-08 发布日期:2014-04-26
  • 通讯作者: 章伟光，范军
  • 基金资助:

    国家自然科学基金项目（21171059）；科技部中小型企业技术创新基金项目（13C26214404534）；广东省科技计划项目（2011B010400023，2012B010900043）；广州市创新基金项目（2013J4400027）.

Preparation of a new immobilized cellulose-based chiral stationary phase and its enantioseparation behaviors

TU Hongsheng1, FAN Jun1, TAN Yi2, LIN Chun1, HUA Jiangying1, ZHANG Weiguang1,2   

  1. 1. School of Chemistry and Environment, South China Normal University, Guangzhou 510006, China;
    2. Guangzhou Research & Creativity Biotechnology Co. Ltd., Guangzhou 510663, China
  • Received:2014-01-13 Revised:2014-03-01 Online:2014-05-08 Published:2014-04-26

PDF

335

被引次数

21

摘要：

键合型多糖手性固定相因具有化学稳定性高和溶剂耐受性好的特点而受到研究者的极大关注。采用施陶丁格（Staudinger）反应将6-叠氮-6-脱氧纤维素-3，5-二氯苯基氨基甲酸酯键合到氨丙基硅胶上得到一种新的键合型手性固定相（ImCel），研究了其手性分离性能，并探讨了非常规流动相（如氯仿、四氢呋喃等）的影响。结果表明，在20对手性化合物中，17对在合适的流动相下得到基线分离。ImCel在正相条件下的分离性能优于反相条件，且在含氯仿的流动相中仍对手性化合物表现出良好的分离能力。在分离一系列芴甲氧羰基（fmoc）-氨基酸衍生物时，ImCel与键合6-叠氮-6-脱氧纤维素-3，5-二甲基苯基氨基甲酸酯的手性固定相表现出互补性，出现了固定相改变引起的对映体洗脱反转现象。本研究丰富了键合型多糖手性固定相的种类和合成方法，为开发新的键合型手性固定相提供了参考。

关键词: 非常规流动相, 键合型手性固定相, 施陶丁格（Staudinger）反应, 手性拆分, 纤维素

Abstract:

The immobilized polysaccharide-based chiral stationary phase has attracted considerable attention over the past decades due to its high chemical stability, good solvent resistance, great enantioseparation ability, etc. In this study, a new immobilized cellulose chiral stationary phase (denoted as ImCel) was prepared through the Staudinger reaction of 6-azido-6-deoxy-cellulose-3,5-dichlorophenylcarbamate and aminopropyl silica gel. The enantioseparation performance of the ImCel for 20 pairs of chiral analytes and the effect of non-standard solvents have been investigated by high performance liquid chromatography. Baseline separations of 17 pairs of enantiomers were achieved on the ImCel. The separation ability of the ImCel in the normal mode was much better than in reversed mode. In addition, the ImCel showed good chemical stability in the non-standard mobile phase due to the covalent bonds between the cellulose chiral selectors and silica support. Moreover, it exhibited complementarity with another immobilized-cellulose chiral stationary phase containing 3,5-dimethylphenylcarbamate groups for the separation of a series of 9-fluorenylmethyloxycarbonyl (fmoc)-derived amino acids. The reversal of enantiomer elution order induced by the difference of the substituents in chiral stationary phase was observed under the same chromatographic conditions. In brief, a new immobilized cellulose chiral stationary phase with high stability and good separation performance was developed in this work.

Key words: cellulose, enantioseparation, immobilized chiral stationary phase, non-standard solvent, Staudinger reaction

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