硅基亲水作用液相色谱固定相的制备及应用研究
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摘要
随着蛋白质组学、代谢组学、中药现代化、环境保护等研究领域的迅速发展,强极性和亲水性的小分子物质迅速成为分析化学和生物化学领域的重要研究对象,但这类物质往往较难在传统的液相色谱柱上得到有效分离,因此限制了它们的应用。亲水作用色谱(HILIC)作为一种新型的色谱分离模式应运而生,已经被证明是一种适用于强极性和亲水性样品定性定量分析的可靠手段。目前,亲水色谱固定相的种类十分有限,因此,亲水作用色谱固定相的制备和应用研究具有重要的意义。本论文在文献调研的基础上,制备了四种新型硅基HILIC固定相,并对它们的色谱分离性能及分离机理进行了研究。
本论文主要包括以下研究内容：
1.采用“无溶剂微波辅助有机合成”法合成了一种咪唑啉分子,通过聚合反应将其固定于多孔硅胶表面。所制备的固定相由憎水的烷基酯链和亲水的咪唑啉环构成,因此赋予其亲水作用色谱和反相色谱的特征。滴定曲线表明该材料在9-4的pH范围内具有缓冲能力,并且随着pH增加,材料捕获的正电荷越多,而且只有在高pH时,该材料才是两性的。在高有机溶剂流动相中,通过研究柱温、流动相中水含量、pH值和离子强度对极性化合物保留时间的影响,发现该分离材料可以用作亲水作用色谱固定相,并且显示出复合的保留机理,主要包括分配、吸附和静电作用。此外,还研究了芳香化合物在不同流动相条件下的保留行为,结果表明：在反相色谱模式下,该固定相的保留基于分配机理。在此新固定相上,六种水溶性维他命和五种芳香化合物分别在亲水和反相色谱模式下实现了高效分离。
2.制备了一种磺化/甲基丙烯酰化的多糖衍生物,并且通过聚合反应成功的键合于多孔硅胶表面。此多糖衍生物在所制备的材料上的固定量为10.33%。新固定相具有亲水作用色谱和富水作用色谱的特征。为了考察该多糖固定相在富水流动相中的特点,研究了柱温、流动相中水含量、pH值和离子强度对测试化合物保留时间的影响。当流速为1.0mL/min,流动相中water/ACN (v/v)为97/3时,苯甲酸在该固定相上的柱效可达31000plates/m。与C18柱相比,该新固定相相对弱极性和非极性化合物有更弱的保留,而对强极性化合物有更强的保留。结果表明,富水作用色谱可以作为亲水作用色谱的替代和反相色谱的补充,应用于极性和亲水性物质的分离。
3.通过在硝酸中回流玉米杆灰制备了粒径为6-18m的碳纳米颗粒。由于羧基和羟基的存在,所获得的经过酸氧化的碳纳米颗粒在水中是可溶的。C13NMR显示,该碳纳米颗粒不同于从蜡烛灰和天然气灰制备的碳纳米颗粒,它主要由sp2和sp3的碳结构构成,而且显示出荧光性质。令人感兴趣的是,可以将CNPs有效地固载于硅胶表面作色谱固定相。所得到的材料可以在亲水作用色谱和富水作用色谱模式下,分离在传统的反相柱上保留困难的极性和亲水性化合物。五种核苷、四种磺胺化合物和红花注射液在亲水和富水色谱条件下实现了高效分离。
4.采用固相合成法,制备了一种环肽(环[-Ala-Ala-Ala-Glu-])固定相。通过茚三酮和紫外/可见光谱测试监测每个氨基酸反应进行的程度。所得到的材料通过紫外光谱、红外光谱、元素分析和热重分析进行了表征,证明环[-Ala-Ala-Ala-Glu-]成功的键合于硅胶表面。该固定相对葸这类多环芳烃显示出立体选择性。同时,分别研究了在水富集流动相和乙腈富集流动相,水含量、柱温、pH值和离子强度变化对极性化合物保留的影响。此外,五种核苷、四种磺胺化合物以及苯酚和苯胺类化合物分别在该环肽固定相上得到相应分离。
With the rapid development of various fields of study in proteomics, metabonomics, the modernization of Chinese traditonal medicine, environmental protection and so on, strong polar and hydrophilic small molecules are rapidly becoming the important objects of study in analytical chemistry and biochemistry fields. However, the separation of polar compounds and highly hydrophilic compounds is difficult on conventional columns. This greatly limits their application. Hydrophilic interaction chromatography (HILIC), as a new type of chromatographic separation mode, came into being and has been proved as a powerful technique in qualitative and quantitive analysis of various kinds of polar and hydrophilic samples. So far, type of HILIC stationary phase is very limited. Therefore, the research for preparation and application of HILIC stationary phase has very important significance. Based on these considerations, four novel silica-based HILIC stationary phases were prepared in this paper. Moreover, their separation performance and mechanism were studied.
The contents are as follows:
1. An imidazoline was prepared by solvent-free microwave-assisted organic synthesis and immobilized on porous silica particles by polymerization. The resulting material was composed of both hydrophobic alkyl ester chains and hydrophilic imidazoline rings, which gave it both hydrophilic interaction and reversed-phase characteristics. The titration curve suggests that the new material has buffering capacity and acquires increasing positive charge over the pH range9-4and is "zwitterionic" in the upper part of this pH range. Through investigating the effect of column temperature, the water content, pH and ion strength of mobile phase on the retention time of polar compounds in highly organic eluents, it was found that the new material could be used as a hydrophilic interaction liquid chromatography stationary phase which involved a complex retention process consisting of partitioning, surface adsorption and electrostatic interactions. In addition, the retention behavior of aromatic compounds in different mobile phase conditions was also studied, which showed the new material mainly exhibited a partitioning mechanism in the reversed-phase liquid chromatography (RPLC) mode. The separation of six water-soluble vitamins and five aromatic compounds were achieved by using the new material in the HILIC and RPLC modes, respectively.
2. The mixed sulfated/methacryloyl polysaccharide derivative was prepared and successfully immobilized onto the surface of porous silica particles by polymerization. Polysaccharide derivative was calculated as10.33%in the stationary phase prepared. The new stationary phase (PMSP) showed both HILIC and per aqueous liquid chromatography (PALC) characteristics. The effects of column temperature, the water content, pH and ion strength of mobile phase on the retention time of test compounds in highly aqueous eluents were investigated to evaluate the PALC features of PMSP. The column efficiency is about31000plates/m for benzoic acid in water/ACN (97/3, v/v) mobile phase at a flow rate of1.0mL/min. Compared with C18column, the PMSP had shorter retention time for weak polar and non-polar compounds, but also showed stronger retention for strong polar compounds. It indicated that PALC was a suitable mode of chromatography as replacement of HILIC and complementarity of reversed-phase liquid chromatography (RPLC).
3. Carbon nanoparticles (CNPs)(6～18nm in size) were prepared by refluxing corn stalk soot in nitric acid. The obtained acid-oxidized CNPs are soluble in water due to the existence of carboxylic and hydroxyl groups. C13NMR measurement shows the CNPs are mainly of sp2and sp3carbon structure different from CNPs obtained from candle soot and natural gas soot. Furthermore, these CNPs exhibit unique photoluminescence properties. Interestingly, the CNPs might be exploited to immobilize on the surface of porous silica particles as chromatographic stationary phase. The resultant packing material was evaluated by high-performance liquid chromatography, indicating that the new stationary phase could be used in HILIC and PALC modes to separate polar compounds and highly hydrophilic compounds lack of retention on conventional reversed-phase columns. The separation of five nucleosides, four sulfa compounds and safflower injection was achieved by using the new column in the HILIC and PALC modes, respectively.
4. Cyclopeptide stationary phase, cyclo[-Ala-Ala-Ala-Glu-], was synthesized by solid-phase synthesis method. Each amino acid coupling step was monitored by the ninhydrin test using UV/Visible spectrophotometry. The proposed material was characterized by UV spectra, FT-IR spectra, elemental analysis and thermogravimetric analysis, which proved the successful immobilization of cyclo[-Ala-Ala-Ala-Glu-] on the silica support. The obtained stationary phase had the stereoselectivity for polycyclic aromatic hydrocarbon such as athracene. Retention behavior of polar compounds was studied through varying the water content, column temperature, pH and ion strength in corresponding acetonitrile-rich and water-rich mobile phases. The separation of five nucleosides, five sulfa compounds and phenol compounds were investigated by using the new column in acetonitrile-rich and water-rich mobile phases, respectively.
本论文主要包括以下研究内容：
1.采用“无溶剂微波辅助有机合成”法合成了一种咪唑啉分子,通过聚合反应将其固定于多孔硅胶表面。所制备的固定相由憎水的烷基酯链和亲水的咪唑啉环构成,因此赋予其亲水作用色谱和反相色谱的特征。滴定曲线表明该材料在9-4的pH范围内具有缓冲能力,并且随着pH增加,材料捕获的正电荷越多,而且只有在高pH时,该材料才是两性的。在高有机溶剂流动相中,通过研究柱温、流动相中水含量、pH值和离子强度对极性化合物保留时间的影响,发现该分离材料可以用作亲水作用色谱固定相,并且显示出复合的保留机理,主要包括分配、吸附和静电作用。此外,还研究了芳香化合物在不同流动相条件下的保留行为,结果表明：在反相色谱模式下,该固定相的保留基于分配机理。在此新固定相上,六种水溶性维他命和五种芳香化合物分别在亲水和反相色谱模式下实现了高效分离。
2.制备了一种磺化/甲基丙烯酰化的多糖衍生物,并且通过聚合反应成功的键合于多孔硅胶表面。此多糖衍生物在所制备的材料上的固定量为10.33%。新固定相具有亲水作用色谱和富水作用色谱的特征。为了考察该多糖固定相在富水流动相中的特点,研究了柱温、流动相中水含量、pH值和离子强度对测试化合物保留时间的影响。当流速为1.0mL/min,流动相中water/ACN (v/v)为97/3时,苯甲酸在该固定相上的柱效可达31000plates/m。与C18柱相比,该新固定相相对弱极性和非极性化合物有更弱的保留,而对强极性化合物有更强的保留。结果表明,富水作用色谱可以作为亲水作用色谱的替代和反相色谱的补充,应用于极性和亲水性物质的分离。
3.通过在硝酸中回流玉米杆灰制备了粒径为6-18m的碳纳米颗粒。由于羧基和羟基的存在,所获得的经过酸氧化的碳纳米颗粒在水中是可溶的。C13NMR显示,该碳纳米颗粒不同于从蜡烛灰和天然气灰制备的碳纳米颗粒,它主要由sp2和sp3的碳结构构成,而且显示出荧光性质。令人感兴趣的是,可以将CNPs有效地固载于硅胶表面作色谱固定相。所得到的材料可以在亲水作用色谱和富水作用色谱模式下,分离在传统的反相柱上保留困难的极性和亲水性化合物。五种核苷、四种磺胺化合物和红花注射液在亲水和富水色谱条件下实现了高效分离。
4.采用固相合成法,制备了一种环肽(环[-Ala-Ala-Ala-Glu-])固定相。通过茚三酮和紫外/可见光谱测试监测每个氨基酸反应进行的程度。所得到的材料通过紫外光谱、红外光谱、元素分析和热重分析进行了表征,证明环[-Ala-Ala-Ala-Glu-]成功的键合于硅胶表面。该固定相对葸这类多环芳烃显示出立体选择性。同时,分别研究了在水富集流动相和乙腈富集流动相,水含量、柱温、pH值和离子强度变化对极性化合物保留的影响。此外,五种核苷、四种磺胺化合物以及苯酚和苯胺类化合物分别在该环肽固定相上得到相应分离。
With the rapid development of various fields of study in proteomics, metabonomics, the modernization of Chinese traditonal medicine, environmental protection and so on, strong polar and hydrophilic small molecules are rapidly becoming the important objects of study in analytical chemistry and biochemistry fields. However, the separation of polar compounds and highly hydrophilic compounds is difficult on conventional columns. This greatly limits their application. Hydrophilic interaction chromatography (HILIC), as a new type of chromatographic separation mode, came into being and has been proved as a powerful technique in qualitative and quantitive analysis of various kinds of polar and hydrophilic samples. So far, type of HILIC stationary phase is very limited. Therefore, the research for preparation and application of HILIC stationary phase has very important significance. Based on these considerations, four novel silica-based HILIC stationary phases were prepared in this paper. Moreover, their separation performance and mechanism were studied.
The contents are as follows:
1. An imidazoline was prepared by solvent-free microwave-assisted organic synthesis and immobilized on porous silica particles by polymerization. The resulting material was composed of both hydrophobic alkyl ester chains and hydrophilic imidazoline rings, which gave it both hydrophilic interaction and reversed-phase characteristics. The titration curve suggests that the new material has buffering capacity and acquires increasing positive charge over the pH range9-4and is "zwitterionic" in the upper part of this pH range. Through investigating the effect of column temperature, the water content, pH and ion strength of mobile phase on the retention time of polar compounds in highly organic eluents, it was found that the new material could be used as a hydrophilic interaction liquid chromatography stationary phase which involved a complex retention process consisting of partitioning, surface adsorption and electrostatic interactions. In addition, the retention behavior of aromatic compounds in different mobile phase conditions was also studied, which showed the new material mainly exhibited a partitioning mechanism in the reversed-phase liquid chromatography (RPLC) mode. The separation of six water-soluble vitamins and five aromatic compounds were achieved by using the new material in the HILIC and RPLC modes, respectively.
2. The mixed sulfated/methacryloyl polysaccharide derivative was prepared and successfully immobilized onto the surface of porous silica particles by polymerization. Polysaccharide derivative was calculated as10.33%in the stationary phase prepared. The new stationary phase (PMSP) showed both HILIC and per aqueous liquid chromatography (PALC) characteristics. The effects of column temperature, the water content, pH and ion strength of mobile phase on the retention time of test compounds in highly aqueous eluents were investigated to evaluate the PALC features of PMSP. The column efficiency is about31000plates/m for benzoic acid in water/ACN (97/3, v/v) mobile phase at a flow rate of1.0mL/min. Compared with C18column, the PMSP had shorter retention time for weak polar and non-polar compounds, but also showed stronger retention for strong polar compounds. It indicated that PALC was a suitable mode of chromatography as replacement of HILIC and complementarity of reversed-phase liquid chromatography (RPLC).
3. Carbon nanoparticles (CNPs)(6～18nm in size) were prepared by refluxing corn stalk soot in nitric acid. The obtained acid-oxidized CNPs are soluble in water due to the existence of carboxylic and hydroxyl groups. C13NMR measurement shows the CNPs are mainly of sp2and sp3carbon structure different from CNPs obtained from candle soot and natural gas soot. Furthermore, these CNPs exhibit unique photoluminescence properties. Interestingly, the CNPs might be exploited to immobilize on the surface of porous silica particles as chromatographic stationary phase. The resultant packing material was evaluated by high-performance liquid chromatography, indicating that the new stationary phase could be used in HILIC and PALC modes to separate polar compounds and highly hydrophilic compounds lack of retention on conventional reversed-phase columns. The separation of five nucleosides, four sulfa compounds and safflower injection was achieved by using the new column in the HILIC and PALC modes, respectively.
4. Cyclopeptide stationary phase, cyclo[-Ala-Ala-Ala-Glu-], was synthesized by solid-phase synthesis method. Each amino acid coupling step was monitored by the ninhydrin test using UV/Visible spectrophotometry. The proposed material was characterized by UV spectra, FT-IR spectra, elemental analysis and thermogravimetric analysis, which proved the successful immobilization of cyclo[-Ala-Ala-Ala-Glu-] on the silica support. The obtained stationary phase had the stereoselectivity for polycyclic aromatic hydrocarbon such as athracene. Retention behavior of polar compounds was studied through varying the water content, column temperature, pH and ion strength in corresponding acetonitrile-rich and water-rich mobile phases. The separation of five nucleosides, five sulfa compounds and phenol compounds were investigated by using the new column in acetonitrile-rich and water-rich mobile phases, respectively.
引文
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