有机相生物催化酯转换合成没食子酸丙酯的研究
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摘要
非水相生物催化是工业生物催化的一个重要方向,提高非水相生物催化效率是生物催化技术目前面临的重要挑战之一。没食子酸丙酯是一种优良的抗氧化剂和重要的医药中间体。本文研究以单宁酶为催化剂,以单宁酸和正丙醇为底物,在有机溶剂中一步酯转换合成没食子酸丙酯的生物催化过程。
由于酶在水相构象可调、在非水相构象相对刚性,印迹技术可以用于非水相催化中生物酶的超激活。为提高酶的有机相酯转换催化性能,综合应用酶蛋白印迹、抗冻保护和固定化技术,结果显示pH调节、底物印迹和界面激活能显著提高单宁酶的活性,其酯转换催化性能较对照提高了123倍；固定化印迹酶可显著降低由印迹导致的酶团聚,提高印迹酶的表观活力,将印迹酶的表观活力提高了近一倍,底物转化率达到了40%；组合使用TritonX-100、甘露糖和镁离子降低了冻干对酶活性的损失,将酶的底物转化率提高到49%。本研究不仅拓宽了印迹技术的应用范围,也为生物酶的修饰改造提供了参照。
热稳定性分析发现印迹酶Ed为85.54kJ mol-1,半衰期为1710h,明显高于已有报道；热力学分析结果显示在40-60℃内,酶催化酯转换合成没食子酸丙酯的一步催化反应的AG和△Hd分别为97.1～98.4kJmol-1和82.77～82.94kJmmol-1,均低于单宁酶水解、酯化两步反应自由能叠加,表明一步酯转换效率优于两步反应；该一步反应△S为-0.047～-0.045kJ mol-1K-1,显示该反应为非自发过程：反应动力学研究显示40℃时,其Km值为0.054mM,低于文献报道的单宁酸酶解反应的Km值,表明印迹提高了单宁酶的底物亲和力,进而提升了酶的催化性能。
为进一步提高酶促酯转换反应的效率,对有机相生物催化反应体系进行了优化。结果显示有机溶剂的极性对反应影响显著,极性低有利于酶促酯转换反应,体系中的水份和正丙醇含量也显著影响反应；采用半连续催化将使催化效率提高约2.5倍,底物转化效率提高到75%。表明有机相生物催化过程中,反应过程控制可以有效提高酶的催化效率,为工程放大提供了依据。
采用菌丝体直接催化可降低酶分离纯化成本。本研究以黑曲霉菌丝体为催化剂催化单宁酸到没食子酸丙酯的酯转换一步合成,通过反应体系优化和催化方式优化底物转化率也达到43%,说明菌丝体为催化剂用于有机相催化也是可行的。
论文研究结果将为农、林业废弃物到没食子酸丙酯绿色生物合成提供技术支撑；所采用的酶印迹强化措施对非水相酶生物催化有普适意义,为有机相生物合成化学品提供了可借鉴的技术手段。
Biocatalysis in anhydrous medium is an important subdivision of industrial biocatalysis. Presently, to improve biocatalytic efficiency of enzyme is one of key challenges in biocatalytic technology. Propyl gallate (PG) is an excellent antioxidant and is also considered as important pharmaceutical intermediates. In this paper, the study on biocatalytic process in which tannase catalyzed the direct synthesis PG from tannic acid and propanol by transesterification was carried out.
In view of the flexibility of enzymatic conformation in aqueous phase and its rigidity in organic medium, imprinting technique is competent to hyper-activate enzyme in anhydrous phase. Imprinting, cryogenic protection, and immobilization techniques were complexly applied to improve the transesterification-catalyzing performance of tannase in organic media. The results showed that such treatments as pH tunning, substrate imprinting, and interfacial imprinting all hyper activate tannase and improve its biocatalytic performance by123folds relative to the original control. Furthermore, immobilizing the imprinted tannase remarkably relieves its aggregation caused by the imprinting, and thus the immobilization increases the apparent activity of the imprinted enzyme and makes its conversion rate of substrate (CR) reach40%. On the other hand, combinational application of Triton X-100, mannose, and magnesium ions reduces the damage of enzyme activity resulted from lyophilization in the protocol of imprinting and promotes its CR up to49%. Not only does the study broaden the application fields of imprinting technique but also presents a reference for modification of enzyme in the future.
The analysis on thermostability of the imprinted tannase found that its activation energy of irreversible thermal inactivation (Ed) and half-time are85.54kJ mol-1and1710h, respectively, which are more than the previous reports. The thermodynamic analysis of the imprinted tannase indicated that the free energy of Gibbs (ΔG) and enthalpy (ΔH) in enzyme-catalyzing transesterification at40-60℃are97.1～98.4kJ mol-1and82.77～82.94kJ mol-1, respectively, which are lower than the free energy stack from hydrolysis and esterification both catalyzed by tannase. This reveals the biocatalytic efficiency of transesterification (direct synthesis) is higher than that of the two-step biocatalysis composed of hydrolysis and esterification. Entropy of activation of denaturation (ΔS) in the direct synthesis is-0.047～-0.045kJmol-1K-1at40-60℃. It indicates that the reaction cannot run spontaneously. The kinetic analysis of the imprinted tannase showed the Km at40℃is0.054mM, which is less than that in tannic acid-hydrolyzing reaction by tannase. It is inferred that the imprinting enhances the biocatalytic performance of enzyme by improving its affinity to substrate.
The organic reaction system was optimized further to increase the biocatalytic efficiency of the imprinted tannase. The results showed that the polarity of organic solvent has a significant effect on its biocatalytic efficiency. The organic solvent with a lower polarity, in particular, is more suitable for transesterification. Otherwise, water and propanol contents in the reaction mixture also affect the efficicency. The study on the reaction mode showed that semicontinuous catalysis gives rise to the biocatalytic efficiency2.5-fold increment and achieves a CR of75%. It manifests that to control the process of the enzyme-catalyzed transesterification in organic media is capable of improving its catalytic efficiency. The resultant data can be used as the base for PG production in commercial scale.
Direct utilization of mycelium as a biocatalyst instead of pure enzyme avails in diminishing the cost in separation and purification of enzyme. In this study, Aspergillus niger mycelium was applied to catalyze the transesterification from tannic acid to PG. The CR of43%was obtained through optimizations of the reaction system and mode. Consequently, it is concluded that mycelium catalyzing the transesterification in organic media is feasible.
The conclusion in this paper will provide a technical support to ecofriendly synthesize PG with agriculture and forestry residues as raw materials. Moreover, such strengthened measures as imprinting and cryogenic protection not only is widespreadly suitable to biocatalysis in organic media, but also gives a experience means to biosynthesize a few chemicals in organic media.
由于酶在水相构象可调、在非水相构象相对刚性,印迹技术可以用于非水相催化中生物酶的超激活。为提高酶的有机相酯转换催化性能,综合应用酶蛋白印迹、抗冻保护和固定化技术,结果显示pH调节、底物印迹和界面激活能显著提高单宁酶的活性,其酯转换催化性能较对照提高了123倍；固定化印迹酶可显著降低由印迹导致的酶团聚,提高印迹酶的表观活力,将印迹酶的表观活力提高了近一倍,底物转化率达到了40%；组合使用TritonX-100、甘露糖和镁离子降低了冻干对酶活性的损失,将酶的底物转化率提高到49%。本研究不仅拓宽了印迹技术的应用范围,也为生物酶的修饰改造提供了参照。
热稳定性分析发现印迹酶Ed为85.54kJ mol-1,半衰期为1710h,明显高于已有报道；热力学分析结果显示在40-60℃内,酶催化酯转换合成没食子酸丙酯的一步催化反应的AG和△Hd分别为97.1～98.4kJmol-1和82.77～82.94kJmmol-1,均低于单宁酶水解、酯化两步反应自由能叠加,表明一步酯转换效率优于两步反应；该一步反应△S为-0.047～-0.045kJ mol-1K-1,显示该反应为非自发过程：反应动力学研究显示40℃时,其Km值为0.054mM,低于文献报道的单宁酸酶解反应的Km值,表明印迹提高了单宁酶的底物亲和力,进而提升了酶的催化性能。
为进一步提高酶促酯转换反应的效率,对有机相生物催化反应体系进行了优化。结果显示有机溶剂的极性对反应影响显著,极性低有利于酶促酯转换反应,体系中的水份和正丙醇含量也显著影响反应；采用半连续催化将使催化效率提高约2.5倍,底物转化效率提高到75%。表明有机相生物催化过程中,反应过程控制可以有效提高酶的催化效率,为工程放大提供了依据。
采用菌丝体直接催化可降低酶分离纯化成本。本研究以黑曲霉菌丝体为催化剂催化单宁酸到没食子酸丙酯的酯转换一步合成,通过反应体系优化和催化方式优化底物转化率也达到43%,说明菌丝体为催化剂用于有机相催化也是可行的。
论文研究结果将为农、林业废弃物到没食子酸丙酯绿色生物合成提供技术支撑；所采用的酶印迹强化措施对非水相酶生物催化有普适意义,为有机相生物合成化学品提供了可借鉴的技术手段。
Biocatalysis in anhydrous medium is an important subdivision of industrial biocatalysis. Presently, to improve biocatalytic efficiency of enzyme is one of key challenges in biocatalytic technology. Propyl gallate (PG) is an excellent antioxidant and is also considered as important pharmaceutical intermediates. In this paper, the study on biocatalytic process in which tannase catalyzed the direct synthesis PG from tannic acid and propanol by transesterification was carried out.
In view of the flexibility of enzymatic conformation in aqueous phase and its rigidity in organic medium, imprinting technique is competent to hyper-activate enzyme in anhydrous phase. Imprinting, cryogenic protection, and immobilization techniques were complexly applied to improve the transesterification-catalyzing performance of tannase in organic media. The results showed that such treatments as pH tunning, substrate imprinting, and interfacial imprinting all hyper activate tannase and improve its biocatalytic performance by123folds relative to the original control. Furthermore, immobilizing the imprinted tannase remarkably relieves its aggregation caused by the imprinting, and thus the immobilization increases the apparent activity of the imprinted enzyme and makes its conversion rate of substrate (CR) reach40%. On the other hand, combinational application of Triton X-100, mannose, and magnesium ions reduces the damage of enzyme activity resulted from lyophilization in the protocol of imprinting and promotes its CR up to49%. Not only does the study broaden the application fields of imprinting technique but also presents a reference for modification of enzyme in the future.
The analysis on thermostability of the imprinted tannase found that its activation energy of irreversible thermal inactivation (Ed) and half-time are85.54kJ mol-1and1710h, respectively, which are more than the previous reports. The thermodynamic analysis of the imprinted tannase indicated that the free energy of Gibbs (ΔG) and enthalpy (ΔH) in enzyme-catalyzing transesterification at40-60℃are97.1～98.4kJ mol-1and82.77～82.94kJ mol-1, respectively, which are lower than the free energy stack from hydrolysis and esterification both catalyzed by tannase. This reveals the biocatalytic efficiency of transesterification (direct synthesis) is higher than that of the two-step biocatalysis composed of hydrolysis and esterification. Entropy of activation of denaturation (ΔS) in the direct synthesis is-0.047～-0.045kJmol-1K-1at40-60℃. It indicates that the reaction cannot run spontaneously. The kinetic analysis of the imprinted tannase showed the Km at40℃is0.054mM, which is less than that in tannic acid-hydrolyzing reaction by tannase. It is inferred that the imprinting enhances the biocatalytic performance of enzyme by improving its affinity to substrate.
The organic reaction system was optimized further to increase the biocatalytic efficiency of the imprinted tannase. The results showed that the polarity of organic solvent has a significant effect on its biocatalytic efficiency. The organic solvent with a lower polarity, in particular, is more suitable for transesterification. Otherwise, water and propanol contents in the reaction mixture also affect the efficicency. The study on the reaction mode showed that semicontinuous catalysis gives rise to the biocatalytic efficiency2.5-fold increment and achieves a CR of75%. It manifests that to control the process of the enzyme-catalyzed transesterification in organic media is capable of improving its catalytic efficiency. The resultant data can be used as the base for PG production in commercial scale.
Direct utilization of mycelium as a biocatalyst instead of pure enzyme avails in diminishing the cost in separation and purification of enzyme. In this study, Aspergillus niger mycelium was applied to catalyze the transesterification from tannic acid to PG. The CR of43%was obtained through optimizations of the reaction system and mode. Consequently, it is concluded that mycelium catalyzing the transesterification in organic media is feasible.
The conclusion in this paper will provide a technical support to ecofriendly synthesize PG with agriculture and forestry residues as raw materials. Moreover, such strengthened measures as imprinting and cryogenic protection not only is widespreadly suitable to biocatalysis in organic media, but also gives a experience means to biosynthesize a few chemicals in organic media.
引文
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