摘要
色谱柱是色谱分离方法的核心。近年来,整体柱因其制备简单、柱效高等特点而备受关注。以取代硼酸为亲和配基发展起来的硼亲和色谱技术,是对顺式二羟基化合物进行识别、富集和分离的重要手段。因此,将硼亲和技术与整体柱制备相结合而发展起来的分析技术与方法,无疑对顺式二羟基化合物的分析和研究起到促进的作用。然而,目前的硼亲和色谱方法发展还不完善,存在着诸多问题：1)由于常用的硼亲和配基pKa较高,只能在碱性的条件下使用,无法满足生理条件下对生物样品检测的需求；2)硼亲和色谱对顺式二羟基化合物的识别是广谱性的,无法对不同顺式二羟基化合物进行特异性识别；3)目前的硼亲和整体柱的保留容量低,对样品的富集能力较低；4)有少数文献报道了取代硼酸与羟乙基胺化合物存在着相互作用,但其相互作用机理还未见报道。为了了解硼亲和相互作用可能存在的干扰和进一步扩展硼酸功能化材料的功能,有必要对相关机理进行深入的研究。针对以上问题,我们从以下几个方面开展了研究：
首先,在苯硼酸单体中引入吸电子基团降低其pKa值,设计了一种具有硼亲和色谱与氢键色谱双重分离机理的混合模式毛细管整体柱。该整体柱以4-(3-丁烯砜基)苯硼酸(BSPBA)为单体,甲叉双丙烯酰胺(MBAA)为交联剂。由于采用的单体和交连剂均有较强的亲水性,整体柱的反相能力得到有效降低。此外,单体苯硼酸中引入了吸电子基团—砜基,使得该整体柱不仅具备在中性pH条件下对顺式二羟基化合物的硼亲和能力,还在一定程度上增强了氢键相互作用的。从而表现出硼亲和色谱和氢键色谱的混合分离机理,在一根整体柱上实现了二维分离。
其次,发展了一种模拟蛋白A对抗体专一选择性的多孔硼亲和限进整体材料。该整体材料结合了硼酸配基的化学选择性和整体材料的纳米通道的尺寸排阻效应,利用纳米通道内的取代硼酸“分子团队”对抗体Fc-糖链进行识别从而高选择性识别抗体。该整体材料在生理pH条件下能对抗体进行高选择性识别,具有类似于蛋白A的选择性,而且结合后的抗体保持原有免疫活性,可应用于抗体的纯化、富集和固载。
此外,为了硼亲和整体材料的比表面,选择分子结构高度对称的三(2,3环氧基丙基)异氰酸酯和三聚氰胺作为共聚试剂,利用“团队硼亲和”原理,制备了一种具有高比表面、结构均匀、亲水性好的硼亲和整体材料。与文献中的硼亲和整体材料相比,该整体材料不仅比表面积得到了显著提高,还可以在生理pH条件下对小分子顺式二羟基化合物进行特异性的抓取。
最后,采用NMR和HPLC相结合的方法考察了取代硼酸与以p-阻断剂和β-兴奋剂为典型代表的羟乙基胺化合物间的相互作用机理。研究表明：取代硼酸与羟乙基胺化合物间的相互作用通过介质中的质子化的溶剂进行相互作用；该相互作用与常规硼亲和相互作用类似,高环境pH加强该相互作用,而低的环境pH消弱甚至破坏该相互作用；此外,与常规硼亲和相互作用不同,该相互作用高度依赖可质子化溶剂环境,大量非质子溶剂(如乙腈)的存在会破坏取代硼酸与羟乙基胺化合物间的相互作用,这为取代硼酸-羟乙基胺化合物相互作用的调控提供了崭新的手段。以上机理为研究苯硼酸功能化材料对p-阻断剂和p-兴奋剂等重要羟乙基胺化合物的识别和分离、富集提供了重要理论依据。
Chromatographic column is the core of chromatography. Recently, monolithic capillary column emerged as an attractive separated tool because of its easy preparation and high performance. The boronate affinity chromatography (BAC) based on the boronic acid reagent is an important technology for recognization; enrichment and saparation of cis-diol containing biomolecules. It is no doubt that the combination of BAC and monolithic column and development their relevant research will improve the knowledge of cis-diol containing compounds. However, the development of boronate affinity is still imperfect, and it encounters some issues:1) because of the high pKa for the normal boronate reagent, it can not satisfy with the detection of biologic sample;2) the boronic acids are of broadspectrum affinity for the recognization of cis-diol compounds, and it can not specific capture different cis-diol compounds;3) the specific surface area of boronate affinity monolith is small, and the binding capacity for cis-diol is low;4) there are only seldom references mentioned the interaction between boronic acid and hydroxypropyl-amino biomolecules, but their interaction mechanism has not been reported. It is necessary to study the revelant mechanism in order to investigate the interferences in the boronate affinity and wide the function of boronate materials. To solve above issues, we carried out research from the following aspects:
Firstly, we induced the electron-withdrawing group into the phenylboronic acod, and the monolithic capillary with the boronate affinity and hydrogeon separated mechanism was synthesized by in situ free radical polymerization. The4-(3-butenylsulfonyl) phenylboronic acid (BSPBA) is the functional monomer and N, N-methylenebisacrylamide (MBAA) is the crosslinker. Both MBAA and BSPBA are hydrophilic regeants, and the hydrophobility was reduced apparently. BSPBA was selected because its lower pKa value (7.0) enables stronger affinity at neutral pH. Besides, the strong electron-withdrawing sulfonyl group greatly reduces the hydrophobicity of the monomer and enhances the hydrogen bonding interaction. So, the monolithic capillary exhibited secondary separation capability, which enables2D separation on a single column.
Secondly, we present a restricted access boronate affinity porous monolith, as a mimic of protein A with high selectity for the specific capture of antibodies. This biomimetic relies on a novel strategy that combines the steric hindrance of the porous monolith with the chemical selectivity of boronic acid. Meanwhile, original immunoaffinity and specificity of the captured antibodies were maintained. The boronic acid ligand well-located within appropriate nanochannels permits specific binding with the glycan of immunoglobulin G (IgG). The restricted access boronate affinity porous monolith can enrich and immobilize the andibodies under physiology pH conditioan, and it has the similar high selecitivity as protein A. Meanwhile, the antibodies captured by the monolith can maintain their original immunoaffinity and specificity to their defined antigens.
Thirdly, in oder to improve the specific area surface of the boronate affinity, the melamine and TEPIC was selected as the copolymer regeant because of their high degree symetry in molecular stuecture. A monolith with high specific surface area homogeous3D skeleton and well hydrophilcility was preparaed. Compared with the references, the specific surface area was increased apparently. Furthermore, the monolith can specific capture the small biomolecular under physiology pH condition.
At last, the method of NMR and HPLC was used to investigate the interaction between boroate and hyoxypropylamino compounds represented by β-blocker and β-agonist. The results shows that the hydroxypropylamino compounds can colvant through the interaction of B-N between boron atom and amino group, at the same, the hydrogen binding between the hydroxyl group in boronic acid and hydroxyl group in hydroxypropylamino compounds. This interaction similar as the convential boronate affinity, high background pH can enhance it and low background pH can weaken it, even destroy it. Moreover, the interaction between boroate and hyoxypropylamino compounds highly dependend on the protonated solvent environment. A large number of aprotic solvents will destroy the interaction, which afford a new measure for the regulating the interaction between boroate and hyoxypropylamino compounds. All the study provide important theoretical basis for the recognization, separation and enrichment of hyoxypropylamino compounds by phenylboronic acid materials.
引文
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