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利福霉素帽(3-(2-O-β-环糊精)-2-羟丙氧基)丙基硅烷键合硅胶颗粒的制备及其作为高效液相色谱手性固定相的应用。

Preparation and application of rifamycin-capped (3-(2-O-β-cyclodextrin)-2-hydroxypropoxy)-propylsilyl-appended silica particles as chiral stationary phase for high-performance liquid chromatography.

机构信息

Department of Obstetrics and Gynaecology, Yong Loo Lin School of Medicine, National University of Singapore, 5 Lower Kent Ridge Road, Singapore 119074, Singapore.

出版信息

Talanta. 2010 Nov 15;83(1):286-90. doi: 10.1016/j.talanta.2010.08.031. Epub 2010 Aug 27.

DOI:10.1016/j.talanta.2010.08.031
PMID:21035677
Abstract

Rifamycin-capped (3-(2-O-β-cyclodextrin)-2-hydroxypropoxy)-propylsilyl-appended silica particles (RCD-HPS), a new type of substituted β-cyclodextrin-bonded chiral stationary phase (CSP) for high-performance liquid chromatography (HPLC), have been synthesized by the treatment of bromoacetate-substituted-(3-(2-O-β-cyclodextrin)-2-hydroxypropoxy)-propylsilyl-appended silica particles (BACD-HPS) with rifamycin SV in anhydrous acetonitrile. The stationary phase is characterized by means of elemental analysis and Fourier-transform infrared spectroscopy. This new CSP has a chiral selector with two recognition sites: rifamycin and β-cyclodextrin (β-CD). The chromatographic behavior of RCD-HPS was studied with several disubstituted benzenes and some chiral drug compounds under reversed-phase HPLC mobile phase conditions. The results show that RCD-HPS has excellent selectivity for the separation of aromatic positional isomers and enantiomers of chiral compounds due to the cooperative functioning of rifamycin and β-CD.

摘要

利福霉素封端的(3-(2-O-β-环糊精)-2-羟丙氧基)丙基硅烷键合硅胶颗粒(RCD-HPS),一种新型取代β-环糊精键合手性固定相(CSP),用于高效液相色谱(HPLC),通过溴乙酸酯取代的(3-(2-O-β-环糊精)-2-羟丙氧基)丙基硅烷键合硅胶颗粒(BACD-HPS)与利福霉素 SV 在无水乙腈中的反应合成。固定相通过元素分析和傅里叶变换红外光谱进行表征。这种新型 CSP 具有两个识别位点的手性选择剂:利福霉素和β-环糊精(β-CD)。在反相 HPLC 流动相条件下,用几种二取代苯和一些手性药物化合物研究了 RCD-HPS 的色谱行为。结果表明,由于利福霉素和β-CD 的协同作用,RCD-HPS 对芳香族位置异构体和手性化合物对映体的分离具有优异的选择性。

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