生物小分子自组装调控与催化转化研究
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摘要
本论文以生物小分子的功能化与高值化利用为目标,选择肽、糖两类生物小分子为研究对象,分别通过分子自组装和催化转化途径,构建功能化肽类纳米材料和高值糖基平台化学品。
(1)界面调控组装：选择多种不同的表面,研究苯丙氨酸二肽(FF)在不同界面条件下的自组装过程。结果发现FF在水溶液中形成预组装体,进而可在玻璃和微孔膜表面组装成纳米纤维和微囊。研究揭示了苯丙氨酸二肽的界面诱导多级组装行为,并获得了一种新的组装体结构。
(2)溶剂-界面调控组装：采用加热-冷却自组装方式,在水溶液中加入乙腈,可诱导组装体结构由微管向纳米纤维转变,溶剂-界面协同作用下可获得均一的微纳结构。结果表明溶剂氢键受体/供体能力可能是影响FF分子排列的关键因素,而组装体形貌则由溶剂和界面的表面张力决定。
(3)反应调控组装：以氨基酸为起始原料,设计了制备肽类水凝胶的新途径,即采用化学法合成Fmoc-二肽的同时,产物发生自组装形成肽类水凝胶,该方法制备的水凝胶结构与传统自组装情形类似。
(4)多糖调控组装：以魔芋葡甘聚糖(KGM)为稳定剂,制备了Fmoc-FF/KGM复合凝胶。研究发现加入KGM后,复合凝胶的稳定性能与机械性能显著提高,其稳定机制可能与分子的支链结构、吸水性和羟基有关。进一步以多烯紫杉醇为模型药物,以KGM加入量与KGM水解酶为参数实现了药物的可控释放。
(5)木质纤维素酶解制糖过程强化：以玉米芯为木质纤维素原料,提出了常压中温下甲酸-氨水组合预处理与酶解制葡萄糖工艺路线,该工艺实现了玉米芯三大组份的有效分离,同时实现了纤维素高效酶解制葡萄糖。
(6)纤维素酶解制约因素分析：选择多种预处理方式,定量表征了预处理前后玉米芯的物化结构参数,并运用数理统计方法分析了结构与酶解的关系,研究表明纤维素酶解主要取决于可及内表面积、木质素含量和分子间氢键。
(7)葡萄糖催化转化制5-羟甲基糠醛(5-HMF)：设计了酶-酸耦合催化体系,在四硼酸钠作用下通过酶法将葡萄糖转化为果糖,进一步在水/丁醇两相中酸催化脱水制备5-HMF,该工艺实现了常规体系中5-HMF的高效制备。
To functionalize and high-efficiently utilize the small biomolecules, aromatic peptide and monosaccharide were chose as model molecules in this thesis. Since it is difficult to use these molecules directly, we employed two pathways to transform them to functional nanomaterials and high-value chemicals. The first one is "self-assembly" way for peptide-based biomolecules by regulating the assembly process. The other one is "catalytic conversion" way for sugars through enzymatic and chemical catalysis process.
(1) Interface controlled self-assembly of diphenylalanine (FF):Different surfaces were used to regulate the FF self-assembly. We found that FF could self-assemble into a core-branched nanostructure in H2O. The resulting pre-assemblies further assembled into nanofibers and microvesicles on the glass surface and microporous membrane, respectively. Our results reveal a hierarchical and interface-induced assembly behavior of FF, meanwhile, a new structure of FF assemblies was obtained.
(2) Solvent and surface controlled self-assembly of diphenylalanine:Our results show that the structural transition of microtubes assembled in H2O into nanofibers can be easily achieved by introducing CH3CN as co-solvent. Furthermore, the synergism of solvent and surface make it more facile and efficient to obtain the high-uniform assemblies. We proposed that hydrogen-bond donor/acceptor ability may be the major determinants for the supramolecular arrangement of FF, while surface tension may play an important role in the structural transition.
(3) Synthetic reaction driven self-assembly:Amino acids was chose as building units, a new pathway, named reaction-assembly, for preparing peptide-based hydrogels was designed. In the reaction-assembly process, the Fmoc-peptides were synthesized by chemical reaction, meanwhile, the resulting Fmoc-peptides was assembled into hydrogels via non-covalent interactions. The structure of hydrogels is similar with that obtained from traditional assembly pathway using pure Fmoc-peptides as starting materials.
(4) Polysaccharide controlled self-assembly of Fmoc-diphenylalanine (Fmoc-FF): Here konjac glucomannan (KGM) is proposed as a stabilizer for preparing Fmoc-FF/KGM hybrid hydrogel. Results show that the hybrid hydrogel has much higher stability compared to Fmoc-FF hydrogel alone, which may be attributed to the branched chains, a high water-absorption capacity, and the abundant -OH groups of the KGM. Moreover, docetaxel was chosen to study the release behavior. The sustained and controlled drug release from this hybrid hydrogel was achieved by varying the concentrations of KGM and beta-mannanase.
(5) Enzymatic hydrolysis of lignocellulose into sugars:A process was designed to pretreat lignocellulose by using formic acid and aqueous ammonia based on corn cobs. The pretreated corn cobs were then hydrolyzed into sugars by cellulases. This process was demonstrated to fractionate lignocellulose to cellulose, hemicellulose and lignin. It also provides a high cellulose digestibility, thus resulting in a high yield of sugars.
(6) Understanding the key factors that limit cellulose hydrolysis:After different pretreatments, cellulose hydrolysis and measurements of physicochemical characteristics were performed in this work. Partial least squares was then applied to seek the key factors limiting the cellulose digestion. Results show that the most important factor for cellulose digestion was accessible interior surface area, followed by delignification and the destruction of the hydrogen bonds.
(7) Catalytic conversion of glucose into 5-hydroxymethylfurfural (5-HMF):Here a new catalytic system featuring the integration of enzymatic and acid catalysis has been developed for the conversion of glucose into 5-HMF. In this process, borate-assisted isomerase was used to convert glucose into fructose, leading to high fructose yield. The resulting sugar mixtures were dehydrated in water-butanol media to produce 5-HMF.
(1)界面调控组装：选择多种不同的表面,研究苯丙氨酸二肽(FF)在不同界面条件下的自组装过程。结果发现FF在水溶液中形成预组装体,进而可在玻璃和微孔膜表面组装成纳米纤维和微囊。研究揭示了苯丙氨酸二肽的界面诱导多级组装行为,并获得了一种新的组装体结构。
(2)溶剂-界面调控组装：采用加热-冷却自组装方式,在水溶液中加入乙腈,可诱导组装体结构由微管向纳米纤维转变,溶剂-界面协同作用下可获得均一的微纳结构。结果表明溶剂氢键受体/供体能力可能是影响FF分子排列的关键因素,而组装体形貌则由溶剂和界面的表面张力决定。
(3)反应调控组装：以氨基酸为起始原料,设计了制备肽类水凝胶的新途径,即采用化学法合成Fmoc-二肽的同时,产物发生自组装形成肽类水凝胶,该方法制备的水凝胶结构与传统自组装情形类似。
(4)多糖调控组装：以魔芋葡甘聚糖(KGM)为稳定剂,制备了Fmoc-FF/KGM复合凝胶。研究发现加入KGM后,复合凝胶的稳定性能与机械性能显著提高,其稳定机制可能与分子的支链结构、吸水性和羟基有关。进一步以多烯紫杉醇为模型药物,以KGM加入量与KGM水解酶为参数实现了药物的可控释放。
(5)木质纤维素酶解制糖过程强化：以玉米芯为木质纤维素原料,提出了常压中温下甲酸-氨水组合预处理与酶解制葡萄糖工艺路线,该工艺实现了玉米芯三大组份的有效分离,同时实现了纤维素高效酶解制葡萄糖。
(6)纤维素酶解制约因素分析：选择多种预处理方式,定量表征了预处理前后玉米芯的物化结构参数,并运用数理统计方法分析了结构与酶解的关系,研究表明纤维素酶解主要取决于可及内表面积、木质素含量和分子间氢键。
(7)葡萄糖催化转化制5-羟甲基糠醛(5-HMF)：设计了酶-酸耦合催化体系,在四硼酸钠作用下通过酶法将葡萄糖转化为果糖,进一步在水/丁醇两相中酸催化脱水制备5-HMF,该工艺实现了常规体系中5-HMF的高效制备。
To functionalize and high-efficiently utilize the small biomolecules, aromatic peptide and monosaccharide were chose as model molecules in this thesis. Since it is difficult to use these molecules directly, we employed two pathways to transform them to functional nanomaterials and high-value chemicals. The first one is "self-assembly" way for peptide-based biomolecules by regulating the assembly process. The other one is "catalytic conversion" way for sugars through enzymatic and chemical catalysis process.
(1) Interface controlled self-assembly of diphenylalanine (FF):Different surfaces were used to regulate the FF self-assembly. We found that FF could self-assemble into a core-branched nanostructure in H2O. The resulting pre-assemblies further assembled into nanofibers and microvesicles on the glass surface and microporous membrane, respectively. Our results reveal a hierarchical and interface-induced assembly behavior of FF, meanwhile, a new structure of FF assemblies was obtained.
(2) Solvent and surface controlled self-assembly of diphenylalanine:Our results show that the structural transition of microtubes assembled in H2O into nanofibers can be easily achieved by introducing CH3CN as co-solvent. Furthermore, the synergism of solvent and surface make it more facile and efficient to obtain the high-uniform assemblies. We proposed that hydrogen-bond donor/acceptor ability may be the major determinants for the supramolecular arrangement of FF, while surface tension may play an important role in the structural transition.
(3) Synthetic reaction driven self-assembly:Amino acids was chose as building units, a new pathway, named reaction-assembly, for preparing peptide-based hydrogels was designed. In the reaction-assembly process, the Fmoc-peptides were synthesized by chemical reaction, meanwhile, the resulting Fmoc-peptides was assembled into hydrogels via non-covalent interactions. The structure of hydrogels is similar with that obtained from traditional assembly pathway using pure Fmoc-peptides as starting materials.
(4) Polysaccharide controlled self-assembly of Fmoc-diphenylalanine (Fmoc-FF): Here konjac glucomannan (KGM) is proposed as a stabilizer for preparing Fmoc-FF/KGM hybrid hydrogel. Results show that the hybrid hydrogel has much higher stability compared to Fmoc-FF hydrogel alone, which may be attributed to the branched chains, a high water-absorption capacity, and the abundant -OH groups of the KGM. Moreover, docetaxel was chosen to study the release behavior. The sustained and controlled drug release from this hybrid hydrogel was achieved by varying the concentrations of KGM and beta-mannanase.
(5) Enzymatic hydrolysis of lignocellulose into sugars:A process was designed to pretreat lignocellulose by using formic acid and aqueous ammonia based on corn cobs. The pretreated corn cobs were then hydrolyzed into sugars by cellulases. This process was demonstrated to fractionate lignocellulose to cellulose, hemicellulose and lignin. It also provides a high cellulose digestibility, thus resulting in a high yield of sugars.
(6) Understanding the key factors that limit cellulose hydrolysis:After different pretreatments, cellulose hydrolysis and measurements of physicochemical characteristics were performed in this work. Partial least squares was then applied to seek the key factors limiting the cellulose digestion. Results show that the most important factor for cellulose digestion was accessible interior surface area, followed by delignification and the destruction of the hydrogen bonds.
(7) Catalytic conversion of glucose into 5-hydroxymethylfurfural (5-HMF):Here a new catalytic system featuring the integration of enzymatic and acid catalysis has been developed for the conversion of glucose into 5-HMF. In this process, borate-assisted isomerase was used to convert glucose into fructose, leading to high fructose yield. The resulting sugar mixtures were dehydrated in water-butanol media to produce 5-HMF.
引文
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