水解酶的催化多功能性及其串联方法的研究
摘要
酶催化有机合成方法的研究越来越受化学家关注,探索酶催化的新功能,调控酶促反应,通过酶催化多功能性来设计串联反应新方法新途径；为化学的绿色合成提供更有价值的新思路和新技术。
论文研究了脂肪酶催化Friedel-Crafts烷基化反应的新功能,考察了反应条件,包括反应时间、酶源、溶剂、底物的比例、酶浓度、温度、底物结构对脂肪酶催化Friedel-Crafts烷基化反应的影响,合成了13种吲哚衍生物。并通过无酶,BSA及失活的PPL来验证酶活性中心的催化作用,提出了可能的催化机理。
论文研究了脂肪酶催化的亲核加成-消去-Michael加成串联反应的新功能,考察了酶源、反应介质、混合溶剂的比例、酶浓度、温度、反应时间、底物结构对脂肪酶催化该串联反应的影响,结果表明：在水与二氧六环比例为4/1的混合溶剂中,脂肪酶PPL可以催化醛与吲哚的串联反应,合成了26种双分子吲哚衍生物。
论文研究了N-杂环化合物添加对酶促反应的调控作用。发现当酶与咪唑质量比为2/1时,酰化酶的催化Claisen-Schmidt活性显著提高。并通过无酶无咪唑、BSA和咪唑、单酶及单咪唑催化来证实酶活性中心和咪唑的共同的催化作用,提出了可能的催化机理。同时考察了酶源、溶剂、添加剂、反应时间、底物结构对酰化酶与咪唑催化反应的影响；并合成了18种α,β-不饱和羰基化合物。
论文通过调控酰化酶与咪唑共同催化催化芳香醛与酮的Aldol缩合-消去-Michael加成-分子内Aldol缩合-消去串联反应活性,合成了15种新颖的环已烯酮衍生物。考察了反应条件：酶源、溶剂、添加剂、酶与添加剂的比例、底物结构对酰化酶与咪唑催化串联Aldol缩合-消去-Michael加成-分子内Aldol缩合-消去反应的影响,并提出了可能的反应机理。
本论文总共合成了72种化合物,产物经IR,1H-NMR, 13C-NMR, GC-MS, HRMS等手段表征分析和验证。
Enzyme catalysis in organic synthesis has drawn an increasing number of chemist's attention. By exploring of the new function; regulating the enzymatic reaction and designing of a new tandem reaction base on the promiscuity of enzyme, enzyme catalysis provide more valuable new ideas and new technologies for green chemistry.
Lipase was firstly found to catalyze the Friedel-Craft reaction in water. After screening the reaction time, enzyme sources, reaction media, the molar ratio of substrate, temperature and the structure of substrates, the Friedel-Craft reactions of indole derivative andα,β-unsaturated compounds with lipase from porcine pancreas, TypeⅡ(PPL) as catalysis were founded.13 Fridel-Craft adducts were synthesized. The control experiments proved that the active site of PPL were responsible for those enzymatic reaction. The mechanisms for the Friedel-Craft reaction and tandem reaction catalyzed by PPL were also proposed.
The tandem Nucleophilic addition/dehydration/Michael addition of aldehyde and indole with lipase (from porcine pancreas, TypeⅡ) as catalysis was screened. The enzyme sources, reaction media, temperature, the structure of substrate that affects this tandem reaction were investigated systemly. In solvent mixture (water/dioxane=4/1), lipase (from porcine pancreas, TypeⅡ) can catalyze the tandem Nucleophilic addition/dehydration/Michael addition between aldehydes and indole derivatives. After the stepwise process were optimized,26 bis(indolyl)alkanes were prepared in moderate to excellent yields by using PPL as catalyst.
The influence of N-heterocyclic compounds on the enzymatic reaction was investigated. Though investigating enzyme sources, solvent, additive, the ratio of imidazole and acylase, we founded that D-aminoacylase and imidazole could be used as co-catalyze to catalyze the Claisen-Schmidt reaction. When the ratio of D-aminoacylase and imidazole is 2/1, the activity of D-aminoacylase was improved obviously. And 18 tandems Aldol condensation/dehydration adducts were obtained via this method. The control experiments demonstrated that the active site of D-aminoacylase was responsible for the enzymatic reaction. The mechanism for the Claisen-Schmidt reaction catalyzed by D-aminoacylase and imidazole was also proposed.
A single enzyme can catalyze the cascade Aldol condensation-elimination-Michael-intromolecular Aldol condensation-elimination for synthesis of conjugate cyclohexanone-2-ene reaction with imidazole in octane. By investigating enzyme sources, solvent, additive, the ratio of imidazole and acylase, we found that D-aminoacylase and imidazole can co-catalyze this tandem reaction. After the stepwise process was optimized,15 conjugate cyclohexanone-2-enes were prepared. Some control experiments were designed to prove that the enzyme can co-catalyze this cascade reaction with imidazole in octane. The mechanism for the tandem reaction catalyzed by D-aminoacylase and imidazole was also proposed.
In this thesis,72 compounds were synthesized and these compounds were characterized by IR,1H NMR,13C NMR, GC-MS and HRMS.
论文研究了脂肪酶催化Friedel-Crafts烷基化反应的新功能,考察了反应条件,包括反应时间、酶源、溶剂、底物的比例、酶浓度、温度、底物结构对脂肪酶催化Friedel-Crafts烷基化反应的影响,合成了13种吲哚衍生物。并通过无酶,BSA及失活的PPL来验证酶活性中心的催化作用,提出了可能的催化机理。
论文研究了脂肪酶催化的亲核加成-消去-Michael加成串联反应的新功能,考察了酶源、反应介质、混合溶剂的比例、酶浓度、温度、反应时间、底物结构对脂肪酶催化该串联反应的影响,结果表明：在水与二氧六环比例为4/1的混合溶剂中,脂肪酶PPL可以催化醛与吲哚的串联反应,合成了26种双分子吲哚衍生物。
论文研究了N-杂环化合物添加对酶促反应的调控作用。发现当酶与咪唑质量比为2/1时,酰化酶的催化Claisen-Schmidt活性显著提高。并通过无酶无咪唑、BSA和咪唑、单酶及单咪唑催化来证实酶活性中心和咪唑的共同的催化作用,提出了可能的催化机理。同时考察了酶源、溶剂、添加剂、反应时间、底物结构对酰化酶与咪唑催化反应的影响；并合成了18种α,β-不饱和羰基化合物。
论文通过调控酰化酶与咪唑共同催化催化芳香醛与酮的Aldol缩合-消去-Michael加成-分子内Aldol缩合-消去串联反应活性,合成了15种新颖的环已烯酮衍生物。考察了反应条件：酶源、溶剂、添加剂、酶与添加剂的比例、底物结构对酰化酶与咪唑催化串联Aldol缩合-消去-Michael加成-分子内Aldol缩合-消去反应的影响,并提出了可能的反应机理。
本论文总共合成了72种化合物,产物经IR,1H-NMR, 13C-NMR, GC-MS, HRMS等手段表征分析和验证。
Enzyme catalysis in organic synthesis has drawn an increasing number of chemist's attention. By exploring of the new function; regulating the enzymatic reaction and designing of a new tandem reaction base on the promiscuity of enzyme, enzyme catalysis provide more valuable new ideas and new technologies for green chemistry.
Lipase was firstly found to catalyze the Friedel-Craft reaction in water. After screening the reaction time, enzyme sources, reaction media, the molar ratio of substrate, temperature and the structure of substrates, the Friedel-Craft reactions of indole derivative andα,β-unsaturated compounds with lipase from porcine pancreas, TypeⅡ(PPL) as catalysis were founded.13 Fridel-Craft adducts were synthesized. The control experiments proved that the active site of PPL were responsible for those enzymatic reaction. The mechanisms for the Friedel-Craft reaction and tandem reaction catalyzed by PPL were also proposed.
The tandem Nucleophilic addition/dehydration/Michael addition of aldehyde and indole with lipase (from porcine pancreas, TypeⅡ) as catalysis was screened. The enzyme sources, reaction media, temperature, the structure of substrate that affects this tandem reaction were investigated systemly. In solvent mixture (water/dioxane=4/1), lipase (from porcine pancreas, TypeⅡ) can catalyze the tandem Nucleophilic addition/dehydration/Michael addition between aldehydes and indole derivatives. After the stepwise process were optimized,26 bis(indolyl)alkanes were prepared in moderate to excellent yields by using PPL as catalyst.
The influence of N-heterocyclic compounds on the enzymatic reaction was investigated. Though investigating enzyme sources, solvent, additive, the ratio of imidazole and acylase, we founded that D-aminoacylase and imidazole could be used as co-catalyze to catalyze the Claisen-Schmidt reaction. When the ratio of D-aminoacylase and imidazole is 2/1, the activity of D-aminoacylase was improved obviously. And 18 tandems Aldol condensation/dehydration adducts were obtained via this method. The control experiments demonstrated that the active site of D-aminoacylase was responsible for the enzymatic reaction. The mechanism for the Claisen-Schmidt reaction catalyzed by D-aminoacylase and imidazole was also proposed.
A single enzyme can catalyze the cascade Aldol condensation-elimination-Michael-intromolecular Aldol condensation-elimination for synthesis of conjugate cyclohexanone-2-ene reaction with imidazole in octane. By investigating enzyme sources, solvent, additive, the ratio of imidazole and acylase, we found that D-aminoacylase and imidazole can co-catalyze this tandem reaction. After the stepwise process was optimized,15 conjugate cyclohexanone-2-enes were prepared. Some control experiments were designed to prove that the enzyme can co-catalyze this cascade reaction with imidazole in octane. The mechanism for the tandem reaction catalyzed by D-aminoacylase and imidazole was also proposed.
In this thesis,72 compounds were synthesized and these compounds were characterized by IR,1H NMR,13C NMR, GC-MS and HRMS.
引文
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