色谱

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万古霉素手性固定相的制备与对映体分离研究

孟晓荣1,史玲1,周华凤1,侯经国2   

  1. 1. College of Science, Xi’an University of Architecture & Technology, Xi’an 710055, China; 2. College of Chemistry &Chemical Engineering, Northwest Normal University, Lanzhou 730000, China
  • 收稿日期:2004-05-30 修回日期:1900-01-01 出版日期:2005-05-30 发布日期:1988-09-25
  • 通讯作者: 孟晓荣
  • 基金资助:

Preparation of Vancomycin Chiral Stationary Phase and Study of Racemate Separation

MENG Xiaorong1, SHI Ling1, ZHOU Huafeng1, HOU Jingguo2   

  1. 1. College of Science, Xi’an University of Architecture & Technology, Xi’an 710055, China; 2. College of Chemistry &Chemical Engineering, Northwest Normal University, Lanzhou 730000, China
  • Received:2004-05-30 Revised:1900-01-01 Online:2005-05-30 Published:1988-09-25

摘要: 采用双官能团试剂4,4′-二苯基甲烷二异氰酸酯在无水二甲基甲酰胺(DMF)中直接与大环糖肽类抗生素万古霉素及γ-氨丙基硅胶键合,得到环状抗生素手性固定相(CSP)并用于高效液相色谱手性分析。实验结果证实,合成的万古霉素CSP在正相和反相条件下均有一定的拆分能力,其中在反相条件下拆分了17种对映体,显示出其较为广泛的拆分范围,且磷酸缓冲体系略优于三乙胺-乙酸缓冲体系;对一些物质,如D,L-丹酰化氨基酸的拆分有一定的规律,能给出绝对构型信息。所制备的CSP在相体系转化时不发生老化和变性,显示了一定的稳定性。对该CSP的拆分机理进行分析所得到的结果与Armstrong等的分析结果基本一致。

关键词: 高效液相色谱, 固定相, 手性拆分 , 万古霉素

Abstract: By adopting the bifunctional group reagent methylene-di-paraphenylene iso-cyanate (MDI), a ring antibiotic chiral stationary phase (CSP) was prepared in non-aqueous dimethylfomamide (DMF) with vancomycin which is a macrocyclic glycopeptide antibiotics bonded on γ-amidopropyl silica gel. It was used in the chiral separation in high performance liquid chromatography. The results showed that vancomycin CSP synthesized in this way can be well used in enantiomer separation of the chiral compounds in normal and reversed-phase. It can be confirmed that the separation capability in reversed-phase is better than that in normal phase. Seventeen pairs of enantiomers were separated in reversed-phase mode, and the results showed a wide range of application. The phosphorus buffer system was better than the triethylamine-acetic acid buffer system. The resolution of some chiral drugs such as D,L-dansyl amino acid has certain rule, and provides information about absolute configuration. The aging or denaturalization can not happen in the CSP when phase system was transformed, so it has some stability. The mechanism of the separation was analyzed and found to be the same as that of Armstrong.

Key words: stationary phase, chiral separation , vancomycin, high performance liquid chromatography