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3,5-二甲基苯基异氰酸酯替考拉宁和苯基异氰酸酯替考拉宁手性固定相的评价与比较
引用本文:沈报春a,b,张大同a,袁建勇c,徐贝佳a,徐秀珠,a.3,5-二甲基苯基异氰酸酯替考拉宁和苯基异氰酸酯替考拉宁手性固定相的评价与比较[J].中国化学,2009,27(4):628-632.
作者姓名:沈报春a  b  张大同a  袁建勇c  徐贝佳a  徐秀珠  a
作者单位:a.浙江大学化学系,浙江杭州 310027; ;b.昆明医学院药学院,云南昆明 650031; ;c.浙江医药股份有限公司新昌制药厂,浙江新昌 312500 ;
摘    要:用大环抗生素替考拉宁手性固定相(TE CSP)分别与3,5-二甲基苯基异氰酸酯和苯基异氰酸酯反应得到了两种新型的高效液相色谱手性固定相----3,5-二甲基苯基异氰酸酯替考拉宁手性固定相(DMP-TE CSP)和苯基异氰酸酯替考拉宁手性固定相(Ph-TE CSP)。用十八个手性化合物在反相及极性流动相模式对这两种CSP的对映体分离能力进行了评价和比较。在反相流动相中,十二个化合物(包括八个氨基酸和四个非氨基酸化合物----对羟基苯甘氨酸,拉米夫定,醇酸和去甲羟安定)的对映体在这两种手性固定相上都获得了分离,大部分的溶质在DMP-TE上获得了更强的保留和稍好的手性分离效果。在极性流动相中,六个氨基醇类化合物在DMP-TE上获得了更强的保留,但它们在两种CSP上的选择因子几乎没有区别。对自制的替考拉宁衍生物手性固定相进行评价和比较,将有助于大环糖肽类抗生素手性固定相手性识别机理的研究。

关 键 词:手性固定相  替考拉宁  3  5-二甲基苯基异氰酸酯  苯基异氰酸酯  对映体分离
收稿时间:2008-4-10
修稿时间:2008-7-4

Evaluation and Comparison of a 3,5‐Dimethylphenyl Isocyanate Teicoplanin and Phenyl Isocyanate Teicoplanin Chiral Stationary Phases
Baochun SHEN,Datong ZHANG,Jianyong YUAN,Beijia XU,Xiuzhu XU.Evaluation and Comparison of a 3,5‐Dimethylphenyl Isocyanate Teicoplanin and Phenyl Isocyanate Teicoplanin Chiral Stationary Phases[J].Chinese Journal of Chemistry,2009,27(4):628-632.
Authors:Baochun SHEN  Datong ZHANG  Jianyong YUAN  Beijia XU  Xiuzhu XU
Institution:1. Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, China;2. School of Pharmaceutical Science, Kunming Medical University, Kunming, Yunnan 650031, China;3. Zhejiang Medicine Co. Ltd, Xinchang Pharmaceutical Factory, Xinchang, Zhejiang 312500, China;4. Tel.: 0086‐0571‐87951290;5. Fax: 0086‐0571‐87951995
Abstract:Two chiral stationary phases (CSP), phenyl isocyanate teicoplanin CSP (Ph‐TE) and 3,5‐dimethylphenyl isocyanate teicoplanin CSP (DMP‐TE) were prepared from the macrocyclic glycopeptide teicoplanin CSP (TE) using derivative agents, phenyl isocyanate or 3,5‐dimethylphenyl isocyanate, respectively. The evaluation and comparison of these two self‐made CSP were conducted using HPLC enantiomeric separations in two different mobile phase modes, i.e., the reversed phased (RP) mode and the polar organic (PO) mode. The chromatographic results were given as the retention, selectivity, and resolution factors. Twelve racemic analytes, including eight amino acids and four non‐amino acid compounds, amino‐(4‐hydroxyphenyl) acetic acid, 4‐(1‐hydroxyethyl)‐2‐methoxy phenol, lamivudine and oxazepam reached enantioseparation using the RPLC mobile phase on these two new CSP. The results show that the retention factors and stereoselectivity factors on DMP‐TE are somewhat bigger than those on Ph‐TE for most analytes in the RPLC mobile phase. Six amino alcohols reached enantiomeric separation on these two CSP using the PO mobile phase. The retention of these amino alcohols on DMP‐TE is longer than that on Ph‐TE but the selectivities have little difference between these two CSP. Comparison of the enantiomeric separations using self‐made Ph‐TE and DMP‐TE were conducted in order to gain a better understanding of the chiral recognition mechanism of the macrocyclic glycopeptide CSP.
Keywords:chiral stationary phase  teicoplanin  phenyl isocyanate teicoplanin  3  5‐dimethylphenyl isocyanate teicoplanin  enantiomeric separation
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