基于烯基桥联反应多分离特性杂化整体柱研究
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摘要
作为微分离领域核心之一的整体柱技术，它以其高效的传质性能和卓越的分离性能，日益受到研究者们的重视，已成功应用于蛋白质组学，药用植物学，代谢组学等领域。整体柱主要包括有机基质整体柱和硅胶基质整体柱两种，有机基质整体柱虽然种类繁多但是柱床稳定性较差，硅胶基质整体柱虽然有稳定柱床，但是由于表面衍生繁琐等问题，导致硅胶基质整体柱种类较少。尽管整体柱的应用越来越广，但因为柱材料稳定性和官能团多样性不能统一的，大大限制了整体柱的可持续发展。近年出现的结合有机整体柱和硅胶整体柱优点的简单硅胶基质杂化整体柱（如乙烯基硅胶杂化整体柱（VTMS整体柱），巯丙基整体柱等）和聚合物有机硅胶杂化整体柱在一定程度上能解决柱材料稳定性和多样性结合问题，因此具有很大发展前景，但是目前这类整体柱相关研究不多，应用也有限，基于这种情况，本文中我们基于杂化技术展开硅基整体柱多元化研究及应用。主要内容如下：
首先以纯硅胶整体柱（TMOS整体柱）为研究对象，详细考察了体系中致孔剂PEG、脲以及温度对整体柱结构的影响，我们进一步以VTMS杂化整体柱为研究对象考察了添加有机硅烷后，制备体系中PEG，脲以及温度对整体柱结构的影响。基于上述研究结果，用甲基丙烯酰氧乙基三甲氧基硅烷（γ-MAPS）替代乙烯基三甲氧基硅烷（VTMS）作为前驱体合成γ-MAPS-TMOS杂化整体柱。相比VTMS杂化整体柱，γ-MAPS-TMOS杂化整体柱表面含有高反应活性烯键，因而能在更温和条件下跟其他含烯键的化合物进行自由基聚合，以及跟含巯基的化合物进行巯-烯点击化学反应，从而将各种分子固定到整体柱表面。
酶固定化一直是生化研究者们关注的焦点，其容易变性的弱点对固定化基质和反应提出了很高的要求，本部分中我们采用前一工作中发展的γ-MAPS-TMOS杂化整体柱作为固定基质，通过巯-烯点击化学反应将胰蛋白酶固定在γ-MAPS整体柱上制成酶微反应器，γ-MAPS-TMOS杂化整体柱表面包含的烯键为高活性烯键，因而能够在常温下高效的和酶表面的自由巯基发生反应而将酶键合到整体柱表面。最后我们将制备的酶反应器应用到蛋白的在线酶解中，结果表明具有较好的酶解效率。
我们发展了一种以VTMS杂化整体柱为基础的新型的双相杂化整体柱，整体柱的前段通过在VTMS杂化柱预聚液中添加含磺酸基的高分子单体和引发剂的方法引入阴离子聚合物，后段为不添加高分子单体的VTMS杂化整体柱，通过一步法将聚合物有机硅胶杂化整体柱和VTMS杂化柱无缝连接在一起，由于后段表面含未反应双键，因而可以通过巯-烯点击反应键合不同的功能基。合成的双相整体柱应用于柱上同时富集、分离碱性化合物。进一步蛋白水解物富集分离试验表明该双相整体柱能够应用于复杂体系富集与分离的研究。
基于乙烯基杂化整体柱除采用表面衍生的办法改性表面外，还可以通过一步法合成得到表面含高分子链的聚合物有机硅胶杂化整体柱，但是通常添加单体性质对整体柱孔结构形成具有影响，本章以水溶性可离子化单体为对象，研究了添加不同性质单体时，在保证整体柱形成良好孔结构的前提下，影响单体添加量的决定性因素，研究结果表明，对于强酸性单体和磺酸基两性离子单体在中性盐的状态下有利于增加单体添加量，与之不同的是季铵类单体则在酸性较强的条件下有利单体的添加。通常水解酸为弱酸，因此弱酸单体可以以水解酸的身份大量的添加到预聚合液中。弱碱性单体添加规律受多种条件的综合影响。通过这些规律的研究使得我们能够可控地制备此类杂化整体柱，也为其他类型聚合物有机硅胶杂化整体柱制备提供参考。
两性离子由于其强亲水性一直备受研究者们的关注，基于两性离子单体，目前已经发展了多种有机基质的亲水整体柱，但是亲水分离中高浓度有机相常常容易导致有机柱的溶胀。在第五章中我们以磺酸基两性离子单体（N,N-二甲基-N-甲基丙烯酰胺基丙基-N,N-二甲基-N-丙烷磺酸内盐，DMMPPS）为添加单体合成了poly（DMMPPS）有机硅胶杂化整体柱，与有机基质相比这种杂化基质能在高浓度有机相中保持更好的机械稳定性。在本章中对poly（DMMPPS）有机硅胶杂化整体柱进行了详细的亲水性评价，并应用于酸性、碱性、中性小分子以及蛋白酶解物的亲水分离。结果表明poly（DMMPPS）有机硅胶杂化整体柱具有较强亲水性和优异的分离性能，且具有分离复杂性亲水化合物的潜力。
As one of the core technologies in nano/micro-separation field，monolithic columntechnology is increasingly attracting the attention of researchers, due to its high mass transferand excellent separation performance. Up to date, it has been successfully applied in almostall field of life sciences, such as proteomics, metabolomics etc. Monolithic columns aremainly divided into two types, organic polymer-based monoliths and silica-based monoliths.To the best of our knowledge, the organic monolithic column, characterized by a richdiversity of surface groups, is easy to swell when exposed to organic solvents. Compared tothe organic polymer monolith, the silica monolithic column has a more stable column bed, butthe monolith types are very limited, due to the small number of silanes and cumbersomederivation. So more wide application of monolithic column is greatly limited. As an emergingtechnology, the silica matrix hybrid monolithic column, which takes advantage of bothorganic monolith and silica monolith, can resolve the problem to some extent. However,related researches and applications are limited. Given this situation, we focus on thediversification of the silica-based monolith based on hybrid technology. The main content isas follows:
1. effects of the porogen (PEG, urea) and temperature on pore structure formation ofTMOS monolithic column were investigated in detail. Further investigation was carried outusing vinyltrimethoxysilane (VTMS) and tetramethoxysilane (TMOS) as precursor forpreparation of VTMS hybrid monolithic column. The effects of porogen (PEG, urea) andtemperature on pore structure formation of VTMS monolith were also examined. A novelγ-MAPS-TMOS hybrid monolith was synthesized by using γ-methacryloxypropyltrimeth-oxysilane (γ-MAPS) instead of VTMS. Highly reactive vinyl groups were formed on thesurface, and further modification via thiol-ene click reaction and radical polymer reactionunder mild condition was achieved.
2. Based on the hybrid organic-inorganic monolithic capillary column, a novel thiol-ene“click” strategy for the preparation of monolithic trypsin microreactor was proposed. It wasfound that the thio-ene click strategy is feasible and simple. In contrast to the conventionalazide-alkyne click reaction, the microreactor can give high catalytic efficiency and stability.The proposed thiol-ene click chemistry strategy is proved to be a promising method for thehighly selective immobilization of proteins under mild conditions, especially for enzymeswith free thiol radicals.
3. A novel method to synthesize sulfo/vinyl biphasic silica hybrid monolithic column byone step was developed for on-column preconcentration. In this method, sulfo-based segmentis located at the inlet of capillary column, which acts as preconcentration column. Close to thepreconcentration column, a vinyl functionalized segment is formed and serves as separationcolumn. Vinyl groups on vinyl functionalized segment are modified with ligand containingsulfhydryl group, such as octadecanethiol and6-mercapto-1-hexanol, via thiol-ene clickreaction. The applicability of this system is demonstrated by successful separation of closelyrelated amines. Good separation and enrichment are obtained. The proposed system is alsosuccessfully applied to complex biological samples, such as peptide, diluted bovine serumalbumin (BSA) hydrolysate, and the results indicate that the system has a capability forpreconcentration of low abundance peptides.
4. A novel strategy for surface modification of silica-based monolith via one-pot methodwas developed in recent year. With this method, a polymer organic silica hybrid monolith canbe fabricated by adding polymer monomer into pre-condensation solution of VTMS monolith.The polymer integrated in monolith could provide better interaction between analytes andstationary phase. However, the adding monomer will lead to a change of composition inpre-condensation solution, and this change usually has greatly impact on pore structureformation of monolith. So the effect of adding monomer on the pore structure is veryimportant for the fabrication of monolith. In this work, the effect of monomer on the porestructure of monolith was investigated in detail. For stronger acidic monomer, the resultindicates that the adding amount of monomer would be depressed by the low pH value ofpre-condensation solution. In contrast, the adding amount of quaternary ammonium monomerwould be promoted under the strong acid conditions (pH <2). For weak acidic monomer,good pore structure of monolith can be obtained in a wide range of monomer concentrations.For weak alkaline monomer, adding amount was affected by many factors, such as porogen(PEG, urea) and temperature.
5. A novel sulfoalkylbetaine-based zwitterionic organic-silica hybrid monolith wassynthesized by using N, N-dimethyl-N-methacrylamidopropyl-N-(3-sulfopropyl) ammoniumbetaine (DMMPPS, netural sulfoalkyl-betaine monomer). The key factors for effect of addingamount of zwitterionic monomer were proved to be pH value of monomer and temperature.The adding amount of zwitterionic monomer was significantly increased when DMMPPS wasused instead of N, N-dimethyl-N-methacryloxyethyl-N-(3-sulfopropyl) ammonium betaine(SPE), and this led to a significantly improved hydrophilicity of the monolith. Within thelinear velocity ranging from1to7mm/s, the DMMPPS-based organic-silica hybrid monolithexhibited good mechanical stability and excellent separation performance. The proposed monolithic column was successfully applied to separate purines/pyrimidines, benzoic acidderivatives and nucleotides, as well as tryptic digest of bovine hemoglobin (BHb) in a nano-hydrophilic chromatography (HILIC) mode, and the result demonstrated that such monolithhas the potential for separation of a variety of hydrophilic substances.
首先以纯硅胶整体柱（TMOS整体柱）为研究对象，详细考察了体系中致孔剂PEG、脲以及温度对整体柱结构的影响，我们进一步以VTMS杂化整体柱为研究对象考察了添加有机硅烷后，制备体系中PEG，脲以及温度对整体柱结构的影响。基于上述研究结果，用甲基丙烯酰氧乙基三甲氧基硅烷（γ-MAPS）替代乙烯基三甲氧基硅烷（VTMS）作为前驱体合成γ-MAPS-TMOS杂化整体柱。相比VTMS杂化整体柱，γ-MAPS-TMOS杂化整体柱表面含有高反应活性烯键，因而能在更温和条件下跟其他含烯键的化合物进行自由基聚合，以及跟含巯基的化合物进行巯-烯点击化学反应，从而将各种分子固定到整体柱表面。
酶固定化一直是生化研究者们关注的焦点，其容易变性的弱点对固定化基质和反应提出了很高的要求，本部分中我们采用前一工作中发展的γ-MAPS-TMOS杂化整体柱作为固定基质，通过巯-烯点击化学反应将胰蛋白酶固定在γ-MAPS整体柱上制成酶微反应器，γ-MAPS-TMOS杂化整体柱表面包含的烯键为高活性烯键，因而能够在常温下高效的和酶表面的自由巯基发生反应而将酶键合到整体柱表面。最后我们将制备的酶反应器应用到蛋白的在线酶解中，结果表明具有较好的酶解效率。
我们发展了一种以VTMS杂化整体柱为基础的新型的双相杂化整体柱，整体柱的前段通过在VTMS杂化柱预聚液中添加含磺酸基的高分子单体和引发剂的方法引入阴离子聚合物，后段为不添加高分子单体的VTMS杂化整体柱，通过一步法将聚合物有机硅胶杂化整体柱和VTMS杂化柱无缝连接在一起，由于后段表面含未反应双键，因而可以通过巯-烯点击反应键合不同的功能基。合成的双相整体柱应用于柱上同时富集、分离碱性化合物。进一步蛋白水解物富集分离试验表明该双相整体柱能够应用于复杂体系富集与分离的研究。
基于乙烯基杂化整体柱除采用表面衍生的办法改性表面外，还可以通过一步法合成得到表面含高分子链的聚合物有机硅胶杂化整体柱，但是通常添加单体性质对整体柱孔结构形成具有影响，本章以水溶性可离子化单体为对象，研究了添加不同性质单体时，在保证整体柱形成良好孔结构的前提下，影响单体添加量的决定性因素，研究结果表明，对于强酸性单体和磺酸基两性离子单体在中性盐的状态下有利于增加单体添加量，与之不同的是季铵类单体则在酸性较强的条件下有利单体的添加。通常水解酸为弱酸，因此弱酸单体可以以水解酸的身份大量的添加到预聚合液中。弱碱性单体添加规律受多种条件的综合影响。通过这些规律的研究使得我们能够可控地制备此类杂化整体柱，也为其他类型聚合物有机硅胶杂化整体柱制备提供参考。
两性离子由于其强亲水性一直备受研究者们的关注，基于两性离子单体，目前已经发展了多种有机基质的亲水整体柱，但是亲水分离中高浓度有机相常常容易导致有机柱的溶胀。在第五章中我们以磺酸基两性离子单体（N,N-二甲基-N-甲基丙烯酰胺基丙基-N,N-二甲基-N-丙烷磺酸内盐，DMMPPS）为添加单体合成了poly（DMMPPS）有机硅胶杂化整体柱，与有机基质相比这种杂化基质能在高浓度有机相中保持更好的机械稳定性。在本章中对poly（DMMPPS）有机硅胶杂化整体柱进行了详细的亲水性评价，并应用于酸性、碱性、中性小分子以及蛋白酶解物的亲水分离。结果表明poly（DMMPPS）有机硅胶杂化整体柱具有较强亲水性和优异的分离性能，且具有分离复杂性亲水化合物的潜力。
As one of the core technologies in nano/micro-separation field，monolithic columntechnology is increasingly attracting the attention of researchers, due to its high mass transferand excellent separation performance. Up to date, it has been successfully applied in almostall field of life sciences, such as proteomics, metabolomics etc. Monolithic columns aremainly divided into two types, organic polymer-based monoliths and silica-based monoliths.To the best of our knowledge, the organic monolithic column, characterized by a richdiversity of surface groups, is easy to swell when exposed to organic solvents. Compared tothe organic polymer monolith, the silica monolithic column has a more stable column bed, butthe monolith types are very limited, due to the small number of silanes and cumbersomederivation. So more wide application of monolithic column is greatly limited. As an emergingtechnology, the silica matrix hybrid monolithic column, which takes advantage of bothorganic monolith and silica monolith, can resolve the problem to some extent. However,related researches and applications are limited. Given this situation, we focus on thediversification of the silica-based monolith based on hybrid technology. The main content isas follows:
1. effects of the porogen (PEG, urea) and temperature on pore structure formation ofTMOS monolithic column were investigated in detail. Further investigation was carried outusing vinyltrimethoxysilane (VTMS) and tetramethoxysilane (TMOS) as precursor forpreparation of VTMS hybrid monolithic column. The effects of porogen (PEG, urea) andtemperature on pore structure formation of VTMS monolith were also examined. A novelγ-MAPS-TMOS hybrid monolith was synthesized by using γ-methacryloxypropyltrimeth-oxysilane (γ-MAPS) instead of VTMS. Highly reactive vinyl groups were formed on thesurface, and further modification via thiol-ene click reaction and radical polymer reactionunder mild condition was achieved.
2. Based on the hybrid organic-inorganic monolithic capillary column, a novel thiol-ene“click” strategy for the preparation of monolithic trypsin microreactor was proposed. It wasfound that the thio-ene click strategy is feasible and simple. In contrast to the conventionalazide-alkyne click reaction, the microreactor can give high catalytic efficiency and stability.The proposed thiol-ene click chemistry strategy is proved to be a promising method for thehighly selective immobilization of proteins under mild conditions, especially for enzymeswith free thiol radicals.
3. A novel method to synthesize sulfo/vinyl biphasic silica hybrid monolithic column byone step was developed for on-column preconcentration. In this method, sulfo-based segmentis located at the inlet of capillary column, which acts as preconcentration column. Close to thepreconcentration column, a vinyl functionalized segment is formed and serves as separationcolumn. Vinyl groups on vinyl functionalized segment are modified with ligand containingsulfhydryl group, such as octadecanethiol and6-mercapto-1-hexanol, via thiol-ene clickreaction. The applicability of this system is demonstrated by successful separation of closelyrelated amines. Good separation and enrichment are obtained. The proposed system is alsosuccessfully applied to complex biological samples, such as peptide, diluted bovine serumalbumin (BSA) hydrolysate, and the results indicate that the system has a capability forpreconcentration of low abundance peptides.
4. A novel strategy for surface modification of silica-based monolith via one-pot methodwas developed in recent year. With this method, a polymer organic silica hybrid monolith canbe fabricated by adding polymer monomer into pre-condensation solution of VTMS monolith.The polymer integrated in monolith could provide better interaction between analytes andstationary phase. However, the adding monomer will lead to a change of composition inpre-condensation solution, and this change usually has greatly impact on pore structureformation of monolith. So the effect of adding monomer on the pore structure is veryimportant for the fabrication of monolith. In this work, the effect of monomer on the porestructure of monolith was investigated in detail. For stronger acidic monomer, the resultindicates that the adding amount of monomer would be depressed by the low pH value ofpre-condensation solution. In contrast, the adding amount of quaternary ammonium monomerwould be promoted under the strong acid conditions (pH <2). For weak acidic monomer,good pore structure of monolith can be obtained in a wide range of monomer concentrations.For weak alkaline monomer, adding amount was affected by many factors, such as porogen(PEG, urea) and temperature.
5. A novel sulfoalkylbetaine-based zwitterionic organic-silica hybrid monolith wassynthesized by using N, N-dimethyl-N-methacrylamidopropyl-N-(3-sulfopropyl) ammoniumbetaine (DMMPPS, netural sulfoalkyl-betaine monomer). The key factors for effect of addingamount of zwitterionic monomer were proved to be pH value of monomer and temperature.The adding amount of zwitterionic monomer was significantly increased when DMMPPS wasused instead of N, N-dimethyl-N-methacryloxyethyl-N-(3-sulfopropyl) ammonium betaine(SPE), and this led to a significantly improved hydrophilicity of the monolith. Within thelinear velocity ranging from1to7mm/s, the DMMPPS-based organic-silica hybrid monolithexhibited good mechanical stability and excellent separation performance. The proposed monolithic column was successfully applied to separate purines/pyrimidines, benzoic acidderivatives and nucleotides, as well as tryptic digest of bovine hemoglobin (BHb) in a nano-hydrophilic chromatography (HILIC) mode, and the result demonstrated that such monolithhas the potential for separation of a variety of hydrophilic substances.
引文
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