实心及中空型磁性高分子复合微球的制备及其固定化脂肪酶的研究
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摘要
脂肪酶(lipase, EC3.1.1.3)是一种重要的生物催化剂,可以催化多种反应,如酯化反应、酯交换反应和水解反应等,在手性药物的制备中尤其具有重要的作用。但是,自由酶稳定性差、易失活、不可重复利用且成本较高,固定化酶技术则可以提高酶的稳定性、实现酶的回收重复使用以及连续化操作、降低成本。本学位论文综述了固定化酶技术的发展及研究现状、磁性高分子复合材料在固定化酶技术中的应用及制备方法,并依此提出了本论文的研究思路和选题指导思想。本论文的主要工作是设计制备了四种磁性固定化载体,将其用于固定化酶,并研究固定化酶的性质,主要取得了如下成果：
(1)乳化法制备磁性海藻酸钠微球及其固定化脂肪酶的研究
采用乳化法将超顺磁性Fe3O4纳米粒子直接包覆于交联的海藻酸钠中,制备了粒径约为25-30nm的超顺磁性海藻酸钠纳米微球。用透射电子显微镜(TEM)、红外光谱(FT-IR)、振动样品磁强计(VSM)等对其进行表征,证明所制备的磁性海藻酸钠纳米微球具有以下优点：粒径小、分散性较好、磁饱和强度高(51.4emu/g)。然后,分别使用戊二醛和环氧氯丙烷对磁性微球功能化,用于共价固定化假丝酵母脂肪酶(CRL),制备了两种固定化酶G-ICRL(醛基固定化)和E-ICRL(环氧基固定化),分别优化了固定化条件,并研究固定化酶的各项性质。结果表明,所制备固定化酶均表现出较高的活力回收,与自由酶相比,固定化酶具有更好的稳定性、pH及温度耐受性,也表现出优良的动力学行为和重复使用性。
(2)自组装法制备柔性功能化载体Fe3O4@海藻酸钠/壳聚糖纳米微球及其固定化酶的研究
首先通过自组装法用Ca2+交联海藻酸钠制备出分散性较好的磁性海藻酸钠纳米粒子,再进一步通过静电作用组装一层壳聚糖,得到Fe3O4@海藻酸钠/壳聚糖微球,然后采用氧化聚乙二醇对磁性微球功能化,制备带有醛基功能基的Fe3O4@海藻酸钠/壳聚糖载体。将未功能化和功能化的磁性微球分别用于固定化CRL,未功能化载体通过吸附法固定化酶得到A-ICRL,功能化载体通过吸附法和共价连接法共同固定化酶得到C-ICRL,分别优化固定化条件。然后,使用海藻酸钠和壳聚糖通过层层自组装法在所得固定化酶的表面加上保护层,以进一步提高固定化酶的稳定性。研究固定化酶的稳定性、动力学行为和重复使用性,发现两种方法制备的固定化酶均表现出优于自由酶的性能,同时也证明通过加保护层来提高固定化酶的稳定性是一种有效可行的方法。
(3)水热法制备中空磁性纳米微球及其固定化脂肪酶的研究
首先通过溶剂热法制备实心Fe3O4微球,再通过高压水热法将实心Fe3O4微球转化成中空Fe3O4微球,对各反应条件进行研究,包括碳源种类、中空诱导剂类型及用量、反应时间,最后推断该转化过程的主要机理是气泡支持的Ostwald熟化过程。并且,中空微球的粒径和中空内径的大小可以通过改变反应时间和中空诱导剂用量来调控。然后,分别采用TEM、FT-IR、VSM、热失重分析仪(TG)、物理吸附仪(BET)和动态光散射仪等表征了中空微球的理化性质,证明该中空磁性微球是外层为介孔壳层内部为中空内腔结构的微球,并且具有较高的磁饱和强度。将中空Fe3O4微球和实心Fe3O4微球用于固定化脂肪酶,中空微球表现出明显的固定化优势。最后,以壳聚糖为碳源、尿素为中空诱导剂制备的中空微球为典型样品,经过功能化以后共价固定化酶,优化固定化条件,研究固定化酶的性质,结果表明,所制备固定化酶相对于自由酶具有更好的稳定性及条件适用性。
(4)分散聚合法制备多孔中空磁性Fe3O4/P(GMA-DVB-St)微球及其固定化脂肪酶的研究
在中空四氧化三铁微球的基础上,首先用油酸改性以增强其亲油性,然后以甲基丙烯酸甲酯(GMA)、苯乙烯(St)为单体,二乙烯基苯(DVB)为交联剂,通过分散聚合法制备得到中空磁性高分子复合微球Fe3O4/P(GMA-DVB-St)。对微球进行TEM、FT-IR、BET等表征,证明该微球是表面为介孔壳层结构,内部为中空内腔且带有环氧基功能基的微球,可以直接与酶分子上的氨基连接共价固定化酶。然后,用中空磁性高分子复合微球Fe3O4/P(GMA-DVB-St)固定化CRL,优化固定化条件,研究固定化酶的性质,表明所制备固定化酶具有较高的活力回收、良好的pH和温度耐受性,与自由酶的动力学指数相比,该固定化酶与底物分子之间也具有较好的亲和性。此外,该固定化酶表现出优异的重复使用性,相比于未聚合改性的中空四氧化三铁微球,中空Fe3O4/P(GMA-DVB-St)微球作载体制备的固定化酶具有更优异的性能。
Lipase (triacylglycerol ester hydrolases, EC3.1.1.3) is a kind of ubiquitous enzymes with various biological activities, including enantioselective hydrolysis and esterification, chiral resolution, synthesis of enantioenriched monomers and macromolecules for polymerization, and other enzymatic reactions. However, the stability of free enzymes is pretty terrible, and their activity, broad applicability and reusability are still needed to be proved. Thus, the technology of enzyme immobilization, which could perform enzyme reuse and prove the stability of enzyme, was developed to overcome these inconveniences. This dissertation reviews the studies of enzyme immobilization, the application of magnetic polymer materials for enzyme immobilization and the preparation of magnetic polymer materials. Thus, we prepared four kinds of magnetic polymer supports for lipase immobilization and studied the properties of immobilized lipase. The main content of this dissertation is list as follows:
(1) Preparation of superparamagnetic sodium alginate nanospheres for covalent immobilization of lipase
Superparamagnetic sodium alginate (SA) nanospheres with diameter around25-30nm were prepared with a water-in-oil emulsion method. The resultant magnetic SA nanopspheres was activated with glutaraldehyde and epichlorohydrin to form nanoscale supports. Candida Rugosa Lipase (CRL), hereby chosen as a model enzyme, was covalently immobilized on the resultant magnetic support. The structure and magnetic behavior of the magnetic nanoparticle were confirmed by transmission electron microscopy(TEM), Fourier transform infrared spectroscopy(FT-IR), and vibrating sample magnetometer(VSM). Then, it was verified that the supports we prepared has obvious advantages:small size, excellent dispersibility and high magnetization (51.4emu/g). The immobilized CRL (ICRL) we prepared displayed excellent stability, pH and temperature tolerance, kenetics behaviour and reusability.
(2) Preparation of superparamagnetic Fe3O4@alginate/chitosan nanospheres by self-assembly and their immobilization for lipase
Superparamagnetic alginate nanospheres with diameter of50nm were prepared by self-assembly of alginate in the solution containing Ca2+; and then superparamagnetic alginate/chitosan nanospheres, which could adsorb lipase directly, were obtained with a following assembly of chitosan based on the electrostatic interaction between alginate and chitosan. Subsequently, oxydic poly (ethylene glycol)(PEG) was used to functionalize the magnetic alginate/chitosan nanospheres. Thus, the magnetic nanospheres with aldehyde group and brush-like structure were formed. With various kinds of characterization, it was verified that the magnetic alginate/chitosan nanospheres held small diameters (around60nm) and displayed superparamagnetism with high saturation magnetization. The candida rugosa lipase (CRL), meanwhile, was immobilized onto the magnetic alginate/chitosan nanospheres non-functionalized or functionalized by electrostatic adsorption and covalent bonding, respectively. Afterwards, the immobilized CRL (ICRL) was coated with covering layers made up of alginate and chitosan by a layer-by-layer (LBL) assembly process. Studying the properties of ICRL such as activity, kinetic behaviors, stability and reusability, the ICRL prepared by covalent bonding was proved to be more excellent than that prepared by electrostatic adsorption. Additionally, coating ICRL with covering layers showed good effect on improving the stability of ICRL.
(3) Building on size-controllable hollow nanospheres with superparamagnetism derived from solid Fe3O4nanospheres:preparation, characterization and application for lipase immobilization
Monodisperse porous hollow nanospheres with superparamagnetism were prepared via a hydrothermal reaction based on solid Fe3O4nanospheres. By investigating the effect of carbon precursors, the kinds and amounts of structure direction agents and the reaction time on the formation of hollow spheres, it was proposed that the main formation mechanism of hollow spheres is a gas-bubble-assisted Ostwald ripening process. Additionally, it is found that the diameter of hollow spheres and the size of hollow core could be adjusted by changing the above factors. The resultant hollow spheres were characterized by means of Brunauer-Emmett-Teller gas sorptometry, transmission electron microscopy, scanning electron microscopy, X-ray diffraction, Fourier-transform infrared spectrophotometer, Thermogravimetric analysis and vibrating sample magnetometer. It is verified that the resultant hollow spheres are porous and have high saturation magnetization. For further application, these hollow spheres were utilized to immobilize CRL and they showed excellent immobilization capacities compared with the solid microspheres. Finally, the resultant ICRL also displayed good applicability and reusability.(4) Preparation of hollow magnetic Fe3O4/P(GMA-DVB-St) microspheres and their application for lipase immobilization
On the basis of hollow magnetic nanoparticles, the monomer GMA and St, the cross-linker DVB were selected to be polymerized to form hollow magnetic Fe3O4/P(GMA-DVB-St) microspheres. It was verified that this hollow microspheres had an especial structures consisting of mesoporous shell and hollow core, which would improve its ability for lipase immobilization. Additionally, there were expoxy groups on the surface of these microspheres due to the existence of GMA, thus, these microspheres could react with lipase directly. Then, we studied the properties of immobilized CRL (ICRL). The ICRL showed excellent stability and reusability. Copared with the ICRL prepared by hollow magnetic nanospheres without polymeric modification, the ICRL prepared by hollow magnetic polymer microspheres displayed more excellent properties.
(1)乳化法制备磁性海藻酸钠微球及其固定化脂肪酶的研究
采用乳化法将超顺磁性Fe3O4纳米粒子直接包覆于交联的海藻酸钠中,制备了粒径约为25-30nm的超顺磁性海藻酸钠纳米微球。用透射电子显微镜(TEM)、红外光谱(FT-IR)、振动样品磁强计(VSM)等对其进行表征,证明所制备的磁性海藻酸钠纳米微球具有以下优点：粒径小、分散性较好、磁饱和强度高(51.4emu/g)。然后,分别使用戊二醛和环氧氯丙烷对磁性微球功能化,用于共价固定化假丝酵母脂肪酶(CRL),制备了两种固定化酶G-ICRL(醛基固定化)和E-ICRL(环氧基固定化),分别优化了固定化条件,并研究固定化酶的各项性质。结果表明,所制备固定化酶均表现出较高的活力回收,与自由酶相比,固定化酶具有更好的稳定性、pH及温度耐受性,也表现出优良的动力学行为和重复使用性。
(2)自组装法制备柔性功能化载体Fe3O4@海藻酸钠/壳聚糖纳米微球及其固定化酶的研究
首先通过自组装法用Ca2+交联海藻酸钠制备出分散性较好的磁性海藻酸钠纳米粒子,再进一步通过静电作用组装一层壳聚糖,得到Fe3O4@海藻酸钠/壳聚糖微球,然后采用氧化聚乙二醇对磁性微球功能化,制备带有醛基功能基的Fe3O4@海藻酸钠/壳聚糖载体。将未功能化和功能化的磁性微球分别用于固定化CRL,未功能化载体通过吸附法固定化酶得到A-ICRL,功能化载体通过吸附法和共价连接法共同固定化酶得到C-ICRL,分别优化固定化条件。然后,使用海藻酸钠和壳聚糖通过层层自组装法在所得固定化酶的表面加上保护层,以进一步提高固定化酶的稳定性。研究固定化酶的稳定性、动力学行为和重复使用性,发现两种方法制备的固定化酶均表现出优于自由酶的性能,同时也证明通过加保护层来提高固定化酶的稳定性是一种有效可行的方法。
(3)水热法制备中空磁性纳米微球及其固定化脂肪酶的研究
首先通过溶剂热法制备实心Fe3O4微球,再通过高压水热法将实心Fe3O4微球转化成中空Fe3O4微球,对各反应条件进行研究,包括碳源种类、中空诱导剂类型及用量、反应时间,最后推断该转化过程的主要机理是气泡支持的Ostwald熟化过程。并且,中空微球的粒径和中空内径的大小可以通过改变反应时间和中空诱导剂用量来调控。然后,分别采用TEM、FT-IR、VSM、热失重分析仪(TG)、物理吸附仪(BET)和动态光散射仪等表征了中空微球的理化性质,证明该中空磁性微球是外层为介孔壳层内部为中空内腔结构的微球,并且具有较高的磁饱和强度。将中空Fe3O4微球和实心Fe3O4微球用于固定化脂肪酶,中空微球表现出明显的固定化优势。最后,以壳聚糖为碳源、尿素为中空诱导剂制备的中空微球为典型样品,经过功能化以后共价固定化酶,优化固定化条件,研究固定化酶的性质,结果表明,所制备固定化酶相对于自由酶具有更好的稳定性及条件适用性。
(4)分散聚合法制备多孔中空磁性Fe3O4/P(GMA-DVB-St)微球及其固定化脂肪酶的研究
在中空四氧化三铁微球的基础上,首先用油酸改性以增强其亲油性,然后以甲基丙烯酸甲酯(GMA)、苯乙烯(St)为单体,二乙烯基苯(DVB)为交联剂,通过分散聚合法制备得到中空磁性高分子复合微球Fe3O4/P(GMA-DVB-St)。对微球进行TEM、FT-IR、BET等表征,证明该微球是表面为介孔壳层结构,内部为中空内腔且带有环氧基功能基的微球,可以直接与酶分子上的氨基连接共价固定化酶。然后,用中空磁性高分子复合微球Fe3O4/P(GMA-DVB-St)固定化CRL,优化固定化条件,研究固定化酶的性质,表明所制备固定化酶具有较高的活力回收、良好的pH和温度耐受性,与自由酶的动力学指数相比,该固定化酶与底物分子之间也具有较好的亲和性。此外,该固定化酶表现出优异的重复使用性,相比于未聚合改性的中空四氧化三铁微球,中空Fe3O4/P(GMA-DVB-St)微球作载体制备的固定化酶具有更优异的性能。
Lipase (triacylglycerol ester hydrolases, EC3.1.1.3) is a kind of ubiquitous enzymes with various biological activities, including enantioselective hydrolysis and esterification, chiral resolution, synthesis of enantioenriched monomers and macromolecules for polymerization, and other enzymatic reactions. However, the stability of free enzymes is pretty terrible, and their activity, broad applicability and reusability are still needed to be proved. Thus, the technology of enzyme immobilization, which could perform enzyme reuse and prove the stability of enzyme, was developed to overcome these inconveniences. This dissertation reviews the studies of enzyme immobilization, the application of magnetic polymer materials for enzyme immobilization and the preparation of magnetic polymer materials. Thus, we prepared four kinds of magnetic polymer supports for lipase immobilization and studied the properties of immobilized lipase. The main content of this dissertation is list as follows:
(1) Preparation of superparamagnetic sodium alginate nanospheres for covalent immobilization of lipase
Superparamagnetic sodium alginate (SA) nanospheres with diameter around25-30nm were prepared with a water-in-oil emulsion method. The resultant magnetic SA nanopspheres was activated with glutaraldehyde and epichlorohydrin to form nanoscale supports. Candida Rugosa Lipase (CRL), hereby chosen as a model enzyme, was covalently immobilized on the resultant magnetic support. The structure and magnetic behavior of the magnetic nanoparticle were confirmed by transmission electron microscopy(TEM), Fourier transform infrared spectroscopy(FT-IR), and vibrating sample magnetometer(VSM). Then, it was verified that the supports we prepared has obvious advantages:small size, excellent dispersibility and high magnetization (51.4emu/g). The immobilized CRL (ICRL) we prepared displayed excellent stability, pH and temperature tolerance, kenetics behaviour and reusability.
(2) Preparation of superparamagnetic Fe3O4@alginate/chitosan nanospheres by self-assembly and their immobilization for lipase
Superparamagnetic alginate nanospheres with diameter of50nm were prepared by self-assembly of alginate in the solution containing Ca2+; and then superparamagnetic alginate/chitosan nanospheres, which could adsorb lipase directly, were obtained with a following assembly of chitosan based on the electrostatic interaction between alginate and chitosan. Subsequently, oxydic poly (ethylene glycol)(PEG) was used to functionalize the magnetic alginate/chitosan nanospheres. Thus, the magnetic nanospheres with aldehyde group and brush-like structure were formed. With various kinds of characterization, it was verified that the magnetic alginate/chitosan nanospheres held small diameters (around60nm) and displayed superparamagnetism with high saturation magnetization. The candida rugosa lipase (CRL), meanwhile, was immobilized onto the magnetic alginate/chitosan nanospheres non-functionalized or functionalized by electrostatic adsorption and covalent bonding, respectively. Afterwards, the immobilized CRL (ICRL) was coated with covering layers made up of alginate and chitosan by a layer-by-layer (LBL) assembly process. Studying the properties of ICRL such as activity, kinetic behaviors, stability and reusability, the ICRL prepared by covalent bonding was proved to be more excellent than that prepared by electrostatic adsorption. Additionally, coating ICRL with covering layers showed good effect on improving the stability of ICRL.
(3) Building on size-controllable hollow nanospheres with superparamagnetism derived from solid Fe3O4nanospheres:preparation, characterization and application for lipase immobilization
Monodisperse porous hollow nanospheres with superparamagnetism were prepared via a hydrothermal reaction based on solid Fe3O4nanospheres. By investigating the effect of carbon precursors, the kinds and amounts of structure direction agents and the reaction time on the formation of hollow spheres, it was proposed that the main formation mechanism of hollow spheres is a gas-bubble-assisted Ostwald ripening process. Additionally, it is found that the diameter of hollow spheres and the size of hollow core could be adjusted by changing the above factors. The resultant hollow spheres were characterized by means of Brunauer-Emmett-Teller gas sorptometry, transmission electron microscopy, scanning electron microscopy, X-ray diffraction, Fourier-transform infrared spectrophotometer, Thermogravimetric analysis and vibrating sample magnetometer. It is verified that the resultant hollow spheres are porous and have high saturation magnetization. For further application, these hollow spheres were utilized to immobilize CRL and they showed excellent immobilization capacities compared with the solid microspheres. Finally, the resultant ICRL also displayed good applicability and reusability.(4) Preparation of hollow magnetic Fe3O4/P(GMA-DVB-St) microspheres and their application for lipase immobilization
On the basis of hollow magnetic nanoparticles, the monomer GMA and St, the cross-linker DVB were selected to be polymerized to form hollow magnetic Fe3O4/P(GMA-DVB-St) microspheres. It was verified that this hollow microspheres had an especial structures consisting of mesoporous shell and hollow core, which would improve its ability for lipase immobilization. Additionally, there were expoxy groups on the surface of these microspheres due to the existence of GMA, thus, these microspheres could react with lipase directly. Then, we studied the properties of immobilized CRL (ICRL). The ICRL showed excellent stability and reusability. Copared with the ICRL prepared by hollow magnetic nanospheres without polymeric modification, the ICRL prepared by hollow magnetic polymer microspheres displayed more excellent properties.
引文
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