改性β-环糊精毛细管电色谱手性整体柱研究
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摘要
毛细管电色谱的分离基础为样品与具有特殊结构的固定相分离材料之间相互作用的差别。β-环糊精的特殊分子结构与整体柱技术相结合发展新型手性分离材料,对于进一步拓宽毛细管电色谱在手性分离方面的应用具有重要意义。
本文采用不同结构的取代基对β-环糊精进行衍生化处理,得到了羟丙基、氨基、天冬氨酸、烯丙基等取代的衍生化β-环糊精,分别采用红外光谱、差热分析法等对这些环糊精衍生物的性能加以表征,说明这些化合物皆具有较好的稳定性和水溶性。在毛细管电泳的分离模式下,对所合成的新型β-环糊精衍生化的手性分离能力加以系统考察,探讨不同取代基β-环糊精衍生物的可能分离机制。
在GMA/EDMA整体柱活性环氧基团上连接天冬氨酸、氨基、羟丙基-β-环糊精及β-环糊精,制备出系列新型毛细管电色谱手性整体柱。对β-环糊精及其衍生物修饰整体柱的键合条件和修饰方法进行了考察,获得了最佳的制备条件。采用傅里叶变换红外光谱、扫描电镜、压汞法分别表征了手性固定相的官能团、内部形貌、孔径大小及分布情况。优化了毛细管电色谱分离条件,对缓冲盐的种类、浓度、pH值和分离柱温等因素进行了考察。四种手性整体柱在电色谱条件下实现了对8种氨基酸、2种手性药物和含美西律的生命样品的高效分离。
采用烯丙基-β-环糊精与GMA共聚的方法制备了烯丙基-β-环糊精毛细管整体柱,这种制柱方法增加了β-环糊精在固定相中的用量,从而有利于提高整体柱对有机分子的协同效应,继而增加整体柱的手性选择性。在电色谱模式下,以分离18种氨基酸对映体作为参考,进行考察整体柱的分离性能。同时将本文所制得的新型电色谱整体柱应用于盐酸美西律、盐酸芬氟拉明和手性农药溴氰菊酯的手性分离,也得到了良好的分离效果。
单独采用烯丙基-β-环糊精和甲基丙烯酸缩水甘油酯基-β-环糊精为聚合功能单体,一步键合制备了烯丙基-β-环糊精和甲基丙烯酸缩水甘油酯基-β-环糊精聚合物手性整体柱。这种制柱方法增加了β-环糊精在固定相中的用量,方法操作简单,从而有效提高了整体柱的手性拆分能力。并通过条件实验找出制备该整体柱的最佳配比,通过优化色谱条件使用烯丙基-β-环糊精手性整体柱成功分离了罗格列酮、酮洛芬、愈创甘油醚对映体,使用甲基丙烯酸缩水甘油酯基-β-环糊精聚合物手性整体柱成功分离了盐酸地匹福林、1-甲基-3-苯基丙胺、愈创甘油醚对映体。
The separation principle of capillary electrochromatography lies in different interaction between samples and stationary phase with special structure. It is important to develop new chiral separation material for widening application of capillary electrochromatography in chiral separation by combiningβ-cyclodextrin with special molecular structure and monolithic material.
Theβ-cyclodextrin was derived by substituents with different structure and the derivedβ-cyclodextrins with hydroxypropyl, amidogen, aspartic acid, allylic as substituting groups were obtained. Theseβ-cyclodextrin derivatives were characterized with IR, elemental analysis and thermal analysis respectively. The results showed that these compounds had better stability and water-solubility. The chiral separation performance of these new typeβ-cyclodextrin derivatives has been fully investigated in CEC mode, and the separation mechanism ofβ-cyclodextrin with different substituents were also discussed.
A series of new chiral stationary phases (CSPs) were prepared by immobilizingβ-CD derived with aspartic acid、amino、hydroxypropyl andβ-CD to epoxy-group of the glycidyl methacrylate-co-ethylene dimethacrylate (GMA/EDMA) monolithic column. The bonding conditions and modification methods ofβ-cyclodextrin and its derivatives onto modified monolithic column were studied to obtain the best preparation conditions. The functional groups, internal surface morphology, pore size and its distribution of chiral stationary phase were characterized by the fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM) and mercury porosimetry (MP). In order to optimize the separation conditions of capillary electrochromatography (CEC), the buffer type, concentration, pH value, column temperature and other factors were also studied. The eight amino acids and two chiral drugs were successfully separated by the fabricated four types of chiral monolith column with optimized conditions.
In this paper, the allyl-β-cyclodextrin was prepared by the copolymerization of allyl-β-cyclodextrin with GMA. This method increased dosage ofβ-cyclodextrins in stationary phase, and consequently it was propitious to enhance synergy effects of organic molecules and chiral selectivity of monolithic column. 18 kinds of amino acid enantiomers were used separated as reference sample through the CEC mode. The separating property of the monolithic column was investigated systematically. At the same time, the chiral drugs Mexiletine Hydrochloride, Fenfluramine Hydrochloride and chiral pesticides Deltamethrin were also separated and the better effect was obtained by the new type electrochromatography monolithic column.
Allyl-β-cyclodextrin and GMA-based-β-cyclodextrin were taken independently as polymerization functional monomer, and the chiral monolithic column of the allyl-β-cyclodextrin polymer and GMA-based-β-cyclodextrin polymer were prepared by one-step bonding method. This method increased the dosage of cyclodextrins in stationary phase, and then it was easy to operate. Consequently the separating ability of the monolithic column was enhanced. In this study, the optimum proportion of the monolithic column was obtained by a large number of experiments. In the selected chromatographic conditions, the enantiomers of rosiglitazone、ketoprofen and guaifenesin were successfully separated.
本文采用不同结构的取代基对β-环糊精进行衍生化处理,得到了羟丙基、氨基、天冬氨酸、烯丙基等取代的衍生化β-环糊精,分别采用红外光谱、差热分析法等对这些环糊精衍生物的性能加以表征,说明这些化合物皆具有较好的稳定性和水溶性。在毛细管电泳的分离模式下,对所合成的新型β-环糊精衍生化的手性分离能力加以系统考察,探讨不同取代基β-环糊精衍生物的可能分离机制。
在GMA/EDMA整体柱活性环氧基团上连接天冬氨酸、氨基、羟丙基-β-环糊精及β-环糊精,制备出系列新型毛细管电色谱手性整体柱。对β-环糊精及其衍生物修饰整体柱的键合条件和修饰方法进行了考察,获得了最佳的制备条件。采用傅里叶变换红外光谱、扫描电镜、压汞法分别表征了手性固定相的官能团、内部形貌、孔径大小及分布情况。优化了毛细管电色谱分离条件,对缓冲盐的种类、浓度、pH值和分离柱温等因素进行了考察。四种手性整体柱在电色谱条件下实现了对8种氨基酸、2种手性药物和含美西律的生命样品的高效分离。
采用烯丙基-β-环糊精与GMA共聚的方法制备了烯丙基-β-环糊精毛细管整体柱,这种制柱方法增加了β-环糊精在固定相中的用量,从而有利于提高整体柱对有机分子的协同效应,继而增加整体柱的手性选择性。在电色谱模式下,以分离18种氨基酸对映体作为参考,进行考察整体柱的分离性能。同时将本文所制得的新型电色谱整体柱应用于盐酸美西律、盐酸芬氟拉明和手性农药溴氰菊酯的手性分离,也得到了良好的分离效果。
单独采用烯丙基-β-环糊精和甲基丙烯酸缩水甘油酯基-β-环糊精为聚合功能单体,一步键合制备了烯丙基-β-环糊精和甲基丙烯酸缩水甘油酯基-β-环糊精聚合物手性整体柱。这种制柱方法增加了β-环糊精在固定相中的用量,方法操作简单,从而有效提高了整体柱的手性拆分能力。并通过条件实验找出制备该整体柱的最佳配比,通过优化色谱条件使用烯丙基-β-环糊精手性整体柱成功分离了罗格列酮、酮洛芬、愈创甘油醚对映体,使用甲基丙烯酸缩水甘油酯基-β-环糊精聚合物手性整体柱成功分离了盐酸地匹福林、1-甲基-3-苯基丙胺、愈创甘油醚对映体。
The separation principle of capillary electrochromatography lies in different interaction between samples and stationary phase with special structure. It is important to develop new chiral separation material for widening application of capillary electrochromatography in chiral separation by combiningβ-cyclodextrin with special molecular structure and monolithic material.
Theβ-cyclodextrin was derived by substituents with different structure and the derivedβ-cyclodextrins with hydroxypropyl, amidogen, aspartic acid, allylic as substituting groups were obtained. Theseβ-cyclodextrin derivatives were characterized with IR, elemental analysis and thermal analysis respectively. The results showed that these compounds had better stability and water-solubility. The chiral separation performance of these new typeβ-cyclodextrin derivatives has been fully investigated in CEC mode, and the separation mechanism ofβ-cyclodextrin with different substituents were also discussed.
A series of new chiral stationary phases (CSPs) were prepared by immobilizingβ-CD derived with aspartic acid、amino、hydroxypropyl andβ-CD to epoxy-group of the glycidyl methacrylate-co-ethylene dimethacrylate (GMA/EDMA) monolithic column. The bonding conditions and modification methods ofβ-cyclodextrin and its derivatives onto modified monolithic column were studied to obtain the best preparation conditions. The functional groups, internal surface morphology, pore size and its distribution of chiral stationary phase were characterized by the fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM) and mercury porosimetry (MP). In order to optimize the separation conditions of capillary electrochromatography (CEC), the buffer type, concentration, pH value, column temperature and other factors were also studied. The eight amino acids and two chiral drugs were successfully separated by the fabricated four types of chiral monolith column with optimized conditions.
In this paper, the allyl-β-cyclodextrin was prepared by the copolymerization of allyl-β-cyclodextrin with GMA. This method increased dosage ofβ-cyclodextrins in stationary phase, and consequently it was propitious to enhance synergy effects of organic molecules and chiral selectivity of monolithic column. 18 kinds of amino acid enantiomers were used separated as reference sample through the CEC mode. The separating property of the monolithic column was investigated systematically. At the same time, the chiral drugs Mexiletine Hydrochloride, Fenfluramine Hydrochloride and chiral pesticides Deltamethrin were also separated and the better effect was obtained by the new type electrochromatography monolithic column.
Allyl-β-cyclodextrin and GMA-based-β-cyclodextrin were taken independently as polymerization functional monomer, and the chiral monolithic column of the allyl-β-cyclodextrin polymer and GMA-based-β-cyclodextrin polymer were prepared by one-step bonding method. This method increased the dosage of cyclodextrins in stationary phase, and then it was easy to operate. Consequently the separating ability of the monolithic column was enhanced. In this study, the optimum proportion of the monolithic column was obtained by a large number of experiments. In the selected chromatographic conditions, the enantiomers of rosiglitazone、ketoprofen and guaifenesin were successfully separated.
引文
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