几种手性化合物的色谱分离方法研究
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摘要
手性化合物的存在是自然界的一种普遍现象。随着科学和技术的发展，人们对对映体的分离有了更加深入的认识，在生物化学、药物化学及有机化学中的不对称合成和催化技术中，对映体的分离与分析显得越来越重要。因此对手性对映体的拆分是很有必要的。目前，用于手性化合物拆分的主要色谱分离方法有薄层色谱、气相色谱、高效液相色谱和毛细管电泳法等。其中薄层色谱、高效液相和毛细管电泳在目前手性化合物的分离中发挥着极其重要的作用。
本文首先利用毛细管电泳成功地对七种手性化合物进行了拆分，并考察了影响分离的因素。另外，合成了三种纤维素的衍生物，把它们制成薄层板或将其涂布在硅胶上，即可得到一类分离范围极广的手性固定相。通过实验条件的优化，使被分离物质在纤维素衍生物薄层板上得到了很好的分离，并且探讨了纤维素衍生物手性固定相的分离机理。
本论文研究主要分为四部分：
第一章内容：介绍了手性化合物对映体分离研究的背景、意义和手性化合物对映体分离的方法。对Pirkle型手性CSPS，纤维素衍生物类手性CSPS，环糊精型CSPS，大环抗生素类CSPS等进行了简要的评述。
第二章内容：本章以本实验室合成的HP-β-CD作为毛细管电泳手性分离的手性选择剂，采用正极进样，利用高效毛细管电泳对氧氟沙星、扑尔敏、苯丙氨酸等七种手性化合物的分离进行了研究，获得较文献报道要好的分离结果。其中，组氨酸在没有用荧光试剂对其进行柱前衍生化的情况下，使其达到基线分离。在手性化合物的毛细管电泳分离过程中，关键的问题是最佳分离条件的选择，在实际研究中需要大量的实验摸索，我们考察了背景电解质的pH、手性选择剂浓度及电解液种类和操作电压等对分离的影响。
第三章内容：以微晶纤维素为原料，苯甲酰氯、对氯苯甲酰氯和邻氯苯甲酰氯为改性试剂，采用超声方法合成了3种纤维素手性固定相。在合成三(4-氯苯甲酰基)纤维素和三(2-氯苯甲酰基)纤维素反应中，优化工艺条件，加入催化剂4-二甲基胺基吡啶，使反应产率大大提高。产物用核磁共振氢谱、红外光谱和元素分析对它们进行了结构表征。分别将三种手性固定相与一定比例的微晶纤维素混合制备手性薄层板，得到机械性能好、表面均匀光滑的手性薄层板，用来拆分了8种手性化合物，通过色谱条件的优化使2-(9-蒽基)-2-甲氧基乙酸、2-(9-蒽基)-2-羟基乙酸、苯丙氨酸和萘普生等8种手性对映体达到了完全分离，并探讨了纤维素衍生物手性固定相的分离机理。
第四章内容：合成了手性填料纤维素衍生物，并涂敷于氨丙基硅胶上，制备成手性固定相。我们通过电子透射显微分析考察了不同涂敷方式(沉积法和蒸发法)对涂敷型硅胶质量的影响。
最后，对整个论文做了总结。
It is an universal phenomenon that chiral compounds exist in nature. With the development of science and technology, people have had a deep insight into the phenomenon of the enantioseparation. Therefore, it is becoming more and more important to analyze and separate chiral substances in biochemistry, medicinal chemistry, and organic chemistry as well as asymmetric synthesis and catalysis. So far, the chiral separations with chromatographic methods are mainly performed by thin-layer chromatography(TLC), gas chromatography(GC), high performance liquid chromatography(HPLC) and high performance capillary electrophoresis(HPCE), etc. TLC, HPLC and HPCE are the most frequently used methods in separations of chiral substances.
Firstly, seven chiral compounds were used as targets for chiral separation by high performance capillary electrophoresis in this thesis. The influence of various factors was systematically investigated. Secondly, three kinds of cellulose tris(benzoate)s were synthesized from microcrystalline cellulose. The cellulose derivatives were used in thin-layer chromatography and were also coated onto silica gel to prepare CSP. The experimental conditions were investigated and optimized and the chiral recognition mechanisms of these CSPs were discussed.
The present paper research mainly constitutes the following four parts:
The first chapter: In this thesis, the literatures on chiral separation were briefly reviewed. The kinds of chiral stationary phases were introduced, especially Pirkle type CSPs, Cellulose derivatives CSPs, cyclodextrin derivatives(CDs) CSPs and macrocyclic glycopeptide CSPs.
The second chapter: In this part, seven chiral molecules were successfully separated and good results were obtained by high performance capillary electrophoresis using HP-β-cyclodextrin as chiral selector when they were injected from cathode. The effects of the pH of the buffer, the concentrations of the CD derivatives, the type of the background electrolyte and the applied voltage on chiral separation were systematically investigated.
The third chapter: Three kinds of chiral stationary phases- Cellulose tribenzoyl(CTB), Cellulose tris(p-chlorobenzoate)(CTPCB) and Cellulose tris(o-chlorobenzoate)(CTOCB) were ultrasonically prepared by the reaction of microcrystalline cellulose with benzoyl chloride, p-chlorobenzoyl chloride and o-chlorobenzoyl chloride. They were characterized by ~1HNMR, IR spectrometry and elemental analysis. The chiral stationary phases were mixed with microcrystalline cellulose and used in thin-layer chromatographic for the separation of some chiral compounds. Eight chiral compounds were completely separated after optimization of mobile phases. The chiral recognition mechanism of CSPs were also discussed.
The last chapter: Cellulose tris(benzoate)s were synthesized by the reaction of microcrystalline cellulose with benzoyl chloride. A chiral stationary phase was prepared by coating cellulose tris(benzoate)s on the silic. The influence on chiral discrimination of the coated loadings way was performed. The surface topographies of the packing materials have been investigated by the scanning electronmicroscope.
At the last, there is a summary about the progresses of the paper.
本文首先利用毛细管电泳成功地对七种手性化合物进行了拆分，并考察了影响分离的因素。另外，合成了三种纤维素的衍生物，把它们制成薄层板或将其涂布在硅胶上，即可得到一类分离范围极广的手性固定相。通过实验条件的优化，使被分离物质在纤维素衍生物薄层板上得到了很好的分离，并且探讨了纤维素衍生物手性固定相的分离机理。
本论文研究主要分为四部分：
第一章内容：介绍了手性化合物对映体分离研究的背景、意义和手性化合物对映体分离的方法。对Pirkle型手性CSPS，纤维素衍生物类手性CSPS，环糊精型CSPS，大环抗生素类CSPS等进行了简要的评述。
第二章内容：本章以本实验室合成的HP-β-CD作为毛细管电泳手性分离的手性选择剂，采用正极进样，利用高效毛细管电泳对氧氟沙星、扑尔敏、苯丙氨酸等七种手性化合物的分离进行了研究，获得较文献报道要好的分离结果。其中，组氨酸在没有用荧光试剂对其进行柱前衍生化的情况下，使其达到基线分离。在手性化合物的毛细管电泳分离过程中，关键的问题是最佳分离条件的选择，在实际研究中需要大量的实验摸索，我们考察了背景电解质的pH、手性选择剂浓度及电解液种类和操作电压等对分离的影响。
第三章内容：以微晶纤维素为原料，苯甲酰氯、对氯苯甲酰氯和邻氯苯甲酰氯为改性试剂，采用超声方法合成了3种纤维素手性固定相。在合成三(4-氯苯甲酰基)纤维素和三(2-氯苯甲酰基)纤维素反应中，优化工艺条件，加入催化剂4-二甲基胺基吡啶，使反应产率大大提高。产物用核磁共振氢谱、红外光谱和元素分析对它们进行了结构表征。分别将三种手性固定相与一定比例的微晶纤维素混合制备手性薄层板，得到机械性能好、表面均匀光滑的手性薄层板，用来拆分了8种手性化合物，通过色谱条件的优化使2-(9-蒽基)-2-甲氧基乙酸、2-(9-蒽基)-2-羟基乙酸、苯丙氨酸和萘普生等8种手性对映体达到了完全分离，并探讨了纤维素衍生物手性固定相的分离机理。
第四章内容：合成了手性填料纤维素衍生物，并涂敷于氨丙基硅胶上，制备成手性固定相。我们通过电子透射显微分析考察了不同涂敷方式(沉积法和蒸发法)对涂敷型硅胶质量的影响。
最后，对整个论文做了总结。
It is an universal phenomenon that chiral compounds exist in nature. With the development of science and technology, people have had a deep insight into the phenomenon of the enantioseparation. Therefore, it is becoming more and more important to analyze and separate chiral substances in biochemistry, medicinal chemistry, and organic chemistry as well as asymmetric synthesis and catalysis. So far, the chiral separations with chromatographic methods are mainly performed by thin-layer chromatography(TLC), gas chromatography(GC), high performance liquid chromatography(HPLC) and high performance capillary electrophoresis(HPCE), etc. TLC, HPLC and HPCE are the most frequently used methods in separations of chiral substances.
Firstly, seven chiral compounds were used as targets for chiral separation by high performance capillary electrophoresis in this thesis. The influence of various factors was systematically investigated. Secondly, three kinds of cellulose tris(benzoate)s were synthesized from microcrystalline cellulose. The cellulose derivatives were used in thin-layer chromatography and were also coated onto silica gel to prepare CSP. The experimental conditions were investigated and optimized and the chiral recognition mechanisms of these CSPs were discussed.
The present paper research mainly constitutes the following four parts:
The first chapter: In this thesis, the literatures on chiral separation were briefly reviewed. The kinds of chiral stationary phases were introduced, especially Pirkle type CSPs, Cellulose derivatives CSPs, cyclodextrin derivatives(CDs) CSPs and macrocyclic glycopeptide CSPs.
The second chapter: In this part, seven chiral molecules were successfully separated and good results were obtained by high performance capillary electrophoresis using HP-β-cyclodextrin as chiral selector when they were injected from cathode. The effects of the pH of the buffer, the concentrations of the CD derivatives, the type of the background electrolyte and the applied voltage on chiral separation were systematically investigated.
The third chapter: Three kinds of chiral stationary phases- Cellulose tribenzoyl(CTB), Cellulose tris(p-chlorobenzoate)(CTPCB) and Cellulose tris(o-chlorobenzoate)(CTOCB) were ultrasonically prepared by the reaction of microcrystalline cellulose with benzoyl chloride, p-chlorobenzoyl chloride and o-chlorobenzoyl chloride. They were characterized by ~1HNMR, IR spectrometry and elemental analysis. The chiral stationary phases were mixed with microcrystalline cellulose and used in thin-layer chromatographic for the separation of some chiral compounds. Eight chiral compounds were completely separated after optimization of mobile phases. The chiral recognition mechanism of CSPs were also discussed.
The last chapter: Cellulose tris(benzoate)s were synthesized by the reaction of microcrystalline cellulose with benzoyl chloride. A chiral stationary phase was prepared by coating cellulose tris(benzoate)s on the silic. The influence on chiral discrimination of the coated loadings way was performed. The surface topographies of the packing materials have been investigated by the scanning electronmicroscope.
At the last, there is a summary about the progresses of the paper.
引文
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