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基于重氮硅烷化硅胶的光辅助制备万古霉素手性固定相及其高效液相色谱对映体拆分评价。

Light-assisted preparation of vancomycin chiral stationary phase based on diazotized silica and its enantioseparation evaluation by high-performance liquid chromatography.

机构信息

Institute of Biomedical Materials and Engineering, College of Chemistry and Chemical Engineering, Qingdao University, Qingdao 266071, China; Laboratory for New Fiber Materials and Modern Textile, Growing Base for State Key Laboratory, College of Materials Science and Engineering, Qingdao University, Qingdao 266071, China.

Institute of Biomedical Materials and Engineering, College of Chemistry and Chemical Engineering, Qingdao University, Qingdao 266071, China.

出版信息

Talanta. 2018 May 15;182:171-177. doi: 10.1016/j.talanta.2018.01.066. Epub 2018 Jan 31.

DOI:10.1016/j.talanta.2018.01.066
PMID:29501137
Abstract

Owing to enantiomers' identical physical and chemical properties, separation work in the chiral environments is still a great challenge.and chemical properties. Chromatographic techniques employing chiral stationary phases (CSPs) have been developed as powerful tools for the chiral analysis and preparation of pure enantiomers. Here we report a facile synthesis of vancomycin stationary phase based on diazotized silica. Monodisperse silica particles were synthesized by a modified Stöber method. The obtained silica particles were modified by self-assembly photosensitive diazoresin (DR) and vancomycin on the surface. After treatment with UV light, the ionic bonding was converted into covalent bonding through a unique photochemistry reaction of DR. Baseline separation of chiral drugs was achieved by using the vancomycin@SiO particles as packing materials in high performance liquid chromatography (HPLC). The effects of separation parameters including elution mode, flow rate and analyte mass on the enantioselectivity of the CSP were investigated in detail. Due to the replacement of highly toxic and moisture sensitive silane agent by water soluble non-toxic DR in the modification of silica microspheres, this method provides a green and easy way to manufacture packing materials for chromatography applications.

摘要

由于对映异构体具有相同的物理和化学性质,因此在手性环境中进行分离工作仍然是一个巨大的挑战。色谱技术采用手性固定相(CSP)已成为手性分析和制备纯对映体的有力工具。在这里,我们报告了一种基于重氮硅石的万古霉素固定相的简便合成方法。通过改进的 Stöber 法合成单分散二氧化硅颗粒。将获得的二氧化硅颗粒通过自组装光敏重氮树脂(DR)和万古霉素在表面上进行修饰。用 UV 光处理后,通过 DR 的独特光化学反应将离子键转化为共价键。将万古霉素@SiO 颗粒用作填充材料在高效液相色谱(HPLC)中实现了手性药物的基线分离。详细研究了分离参数(包括洗脱模式,流速和分析物质量)对 CSP 对映选择性的影响。由于在二氧化硅微球的修饰中用水溶性无毒的 DR 代替了剧毒和吸湿的硅烷试剂,因此该方法为色谱应用提供了一种绿色简便的制造填充材料的方法。

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