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化学学报
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化学学报 ›› 2009, Vol. 67 ›› Issue (17): 2005-2012. 上一篇    下一篇

研究论文

替考拉宁及间甲基苯基异氰酸酯替考拉宁手性固定相的 对映体分离能力评价与比较

沈报春a,b 袁建勇c 徐贝佳b 徐秀珠*,b

  

  1. (a昆明医学院药学院 昆明 650031)
    (b浙江大学化学系 杭州 310027)
    (c浙江医药股份有限公司新昌制药厂 新昌 312500)

  • 投稿日期:2008-11-27 修回日期:2009-02-16 发布日期:2009-09-14
  • 通讯作者: 徐秀珠

Evaluation and Comparison of m-Tolyl Isocyanate Teicoplanin and Teicoplanin Chiral Stationary Phase

Shen, Baochun a,b Yuan, Jianyongc Xu, Beijiab Xu, Xiuzhu*,b

  

  1. (a School of Pharmaceutical Science, Kunming Medical University, Kunming 650031)
    (b Department of Chemistry, Zhejiang University, Hangzhou 310027)
    (c Zhejiang Medicine Co.Ltd, Xinchang Pharmaceutical Factory, Xinchang 312500)
  • Received:2008-11-27 Revised:2009-02-16 Published:2009-09-14
  • Contact: XU Xiu-Zhu

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被引次数

4

由替考拉宁手性固定相(TE CSP)制备出了一种新型的高效液相色谱手性固定相: 间甲基苯基异氰酸酯替考拉宁手性固定相(TI-TE CSP). 在反相流动相中用7种氨基酸和3种非氨基酸化合物对这两种手性固定相的手性分离能力进行了评价和比较. 考察了有机添加剂的种类和浓度, 缓冲液的pH值等条件对10个手性化合物在两种CSP上手性分离的影响, 计算得出了溶质在两种CSP上的手性选择性自由能差值, 同时初步探讨了这些溶质在两种CSP上的手性识别机理. 实验数据表明, 氨基酸在TE上保留更强, 但在TI-TE上得到了更好的手性分离效果. 结果显示, 经间甲基苯基异氰酸酯衍生化后的替考拉宁CSP在反相流动相中的分离能力有所提高.

关键词: 替考拉宁, 手性固定相, 间甲基苯基异氰酸酯, 手性识别机理

A new HPLC chiral stationary phase (CSP), m-tolyl isocyanate teicoplanin (TI-TE), was synthesized from the macrocyclic glycopeptide teicoplanin CSP (TE), using a derivative agent, m-tolyl isocyanate. Evaluation and comparison of these two TE-based CSPs were carried out with 10 recemates, including 7 amino acids and 3 non-amino acid compounds (lamivudine, oxazepam and p-hydroxyphenylglycine), using RPLC mobile phase. The chromatographic results were given as the retention, selectivity, resolution factors and the enantioselective free energy difference corresponding to the separation of the two enantiomers. The effects of pH, organic modifier type and amount were discussed, and the stereoselectivities of the two TE-based CSPs were compared, and the chiral recognition mechanism of TE-based CSP was also discussed. The retention for α-amino acids on TE was somewhat longer than that on TI-TE while chiral selectivity and resolution were bigger on TI-TE. The results show that the derivative CSP gets better selectivity than TE CSP under the RP mode.

Key words: teicoplanin, chiral stationary phase, m-tolyl isocyanate, chiral recognition mechanism