酶催化多组分反应合成氮杂环方法研究
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摘要
酶促合成作为一个新手段已经引起了化学家们广泛的研究兴趣,近年来,许多研究组发现酶具有催化多功能性,比如酰化酶和蛋白酶催化Michael加成、消旋酶催化aldol加成、酰化酶和谷氨酰胺转移酶催化Henry反应等,因此,水解酶可以应用于更多有机合成反应,已取得诸多成果。但是,水解酶催化多组分一锅法反应还鲜有报道,尤其是构筑结构复杂的杂环化合物。
论文研究建立了酰化酶催化醛、氰基乙酰胺和1,3-二羰基化合物三组分一锅合成3,4-二氢吡啶-2-酮方法,发现了酰化酶AA的催化新功能,反应中形成了四个新化学键和一个六元氮杂环,实验通过无酶、BSA和失活酰化酶的对照实验表明了酶催化中心的作用,提出了相应的催化机理；实验考察了酶的种类、溶剂、底物摩尔比、催化剂量和底物结构变化等因素对反应效率的影响,合成了一系列基于3,4-二氢吡啶-2-酮核心的新化合物。
论文研究建立了酰化酶AA催化醛、氰基乙酰胺和乙酰乙酸乙酯或乙酰乙酸环己酯的一锅三组分反应制备吡啶-2-酮的方法,研究提出三组分反应经过Knoevenagel缩合-Michael加成-分子内环化-氧化的多步串联途径；实验考察研究了酶的种类、溶剂、温度、催化剂量和底物结构变化等对反应的影响,通过氮气保护的对照实验数据分析,证实反应中空气起到了氧化剂的作用,把3,4-二氢吡啶-2-酮氧化成了吡啶-2-酮。
论文研究建立了酰化酶AA催化芳香醛、氰基乙酰胺和单酮的三组分反应合成吡啶-2-酮方法；研究发现该反应实际是一个五分子参与的反应,原位生成氢供体(3,4-二氢吡啶-2-酮)和氢受体(Knoevenagel缩合物),实验通过HPLC定量监测两个中间体的转化过程,进一步确认了原位氢转移过程的存在；该方法可以同时合成吡啶-2-酮和α-烷基化腈两个结构骨架,而α-烷基化腈经分离和化学转化可高产率合成p-氨基酸化合物。
论文研究建立了脂肪酶催化靛红、丙二腈和烯酮类三组分一锅法反应合成螺环结构方法；研究考察了酶的种类、溶剂、含水量、催化剂量、底物摩尔比和温度等对反应产率的影响,制备了一系列的螺环化合物；研究结果表明,脂肪酶PPL在DMSO中具有最佳的催化活性；4位取代的靛红几乎不能参与反应,氰基乙酰胺或氰基乙酸乙酯代替丙二腈时,也没有检测到产物,说明底物的空间位阻效应显著。
论文发展了核酸酶催化的靛红衍生物和环酮之间的直接不对称aldol加成反应。详细研究了一系列反应条件对催化活性和立体选择性的影响,包括酶的种类、溶剂、水含量、底物摩尔比和底物结构等。结果表明,体系中添加15%去离子水可以提高核酸酶的催化效率和立体选择性,最高分离产率95%,ee值82%,非对映立体选择性dr值为99/1。
论文总共合成了84种化合物,其中15种3,4-二氢吡啶-2-酮衍生物,34种吡啶-2-酮衍生物,12种螺环化合物,12种aldol加成产物,6种α-烷基化腈衍生物,3种烯酮类化合物,1种制备氨基酸中间体和1种p-氨基酸。产物经1H NMR、13C NMR、 FTIR、HRMS等手段表征分析和验证,证实其中56种为新化合物。
As a new tool, biocatalytic synthesis in organic chemistry has attracted lots of attention. In recent years, many enzymes have shown catalytic promiscuity, such as, acylase and protease catalyzed Michael addition, racemase catalyzed the aldol reaction, acylase and transglutaminase catalyzed Henry reaction, and hydrolase accelerated many achievements in terms of enzymatic organic synthesis. However, enzymatic one-pot multicomponent reactions are scarcely reported, especially to synthesize complicated and bioactive heterocycles.
A direct method to construct3,4-dihydropyridin-2-ones by enzymatic condensation of aldehyde with cyanoacetamide and1,3-dicarbonyl compounds was developed. Four new bonds and one six-member aza-ring were formed by one-pot method. Controlled experiments involving catalyst-free, BSA and denatured AA verified the role of active site, its catalytic mechanism was further proposed. And reaction conditions involving hydrolases, solvents, substrate molar ratios, hydrolase loadings and substrate variations were optimized. A series of new compounds based on the3,4-dihydropyridin-2-one core were synthesized.
The Acylase "Amano"(AA)-catalyzed synthesis of valuable pyridin-2-ones via domino Knoevenagel condensation-Michael addition-intramolecular cyclization-oxidization reaction between aldehyde, cyanoacetamide and ethyl acetoacetate or cyclohexyl acetoacetate was also developed by the one-pot strategy. Reaction conditions involving hydrolases, solvents, temperatures, catalyst loadings and substrate variations were investigated. And controlled reaction under nitrogen atmosphere illustrated that pyridin-2-one was formed via the oxidization by oxygen at the final step.
An efficient approach for the synthesis of highly substituted pyridin-2-one derivatives via Acylase "Amano"(AA)-catalyzed three-component reaction between aromatic aldehyde, cyanoacetamide and ketone was proposed. Studies showed that this reaction involved five molecules, which could in situ generate hydrogen donor (3,4-dihydropyridin-2-one) and hydrogen acceptor (Knoevenagel condensation product). The internal transfer hydrogenation process was further confirmed after we quantitatively detected the transforming course of the two intermediates by HPLC; Using this method, pyridin-2-ones and a-alkylated nitriles could be obtained simultaneously, and the a-alkylated nitrile could be transformed to synthetically important β-amino acids via simple conversions in high isolated yield.
A one-pot three-component reaction of isatin derivatives, malononitrile and ketene catalyzed by PPL was established successfully. The effect of enzymes, solvents, water content, catalyst loading, substrate molar ratios and temperatures on reaction yields was investigated in details, and a series of spirocompounds were obtained. PPL exhibited the highest catalytic activity in DMSO. The4-position substituted isatin, cyanoacetamide or ethyl cyanoacetate barely participated in the reaction due to their steric hindrance.
Nuclease p1was observed to directly catalyze the asymmetric aldol reactions between isatin derivatives and cyclic ketones. The effect of a series of reaction conditions involving enzymes, solvents, water contents, substrate molar ratios and substrate structure on yields and stereoselectivities were investigated in details. The addition of15%deionized water had a large influence on the enzyme activity. The isolated yields was up to95%, ee value was up to82%and dr value was up to>99/1.
In this thesis,84compounds were synthesized including15derivatives of3,4-dihydropyridin-2-one,34products of pyridin-2-one,12spirocompounds,12products of aldol addition,6α-alkylated nitrile derivatives,3ketene compounds,1amino acid intermediates and1β-amino acid. These compounds were characterized by1H NMR,13C NMR, FTIR, and HRMS and56compounds have been confirmed to be new compounds.
论文研究建立了酰化酶催化醛、氰基乙酰胺和1,3-二羰基化合物三组分一锅合成3,4-二氢吡啶-2-酮方法,发现了酰化酶AA的催化新功能,反应中形成了四个新化学键和一个六元氮杂环,实验通过无酶、BSA和失活酰化酶的对照实验表明了酶催化中心的作用,提出了相应的催化机理；实验考察了酶的种类、溶剂、底物摩尔比、催化剂量和底物结构变化等因素对反应效率的影响,合成了一系列基于3,4-二氢吡啶-2-酮核心的新化合物。
论文研究建立了酰化酶AA催化醛、氰基乙酰胺和乙酰乙酸乙酯或乙酰乙酸环己酯的一锅三组分反应制备吡啶-2-酮的方法,研究提出三组分反应经过Knoevenagel缩合-Michael加成-分子内环化-氧化的多步串联途径；实验考察研究了酶的种类、溶剂、温度、催化剂量和底物结构变化等对反应的影响,通过氮气保护的对照实验数据分析,证实反应中空气起到了氧化剂的作用,把3,4-二氢吡啶-2-酮氧化成了吡啶-2-酮。
论文研究建立了酰化酶AA催化芳香醛、氰基乙酰胺和单酮的三组分反应合成吡啶-2-酮方法；研究发现该反应实际是一个五分子参与的反应,原位生成氢供体(3,4-二氢吡啶-2-酮)和氢受体(Knoevenagel缩合物),实验通过HPLC定量监测两个中间体的转化过程,进一步确认了原位氢转移过程的存在；该方法可以同时合成吡啶-2-酮和α-烷基化腈两个结构骨架,而α-烷基化腈经分离和化学转化可高产率合成p-氨基酸化合物。
论文研究建立了脂肪酶催化靛红、丙二腈和烯酮类三组分一锅法反应合成螺环结构方法；研究考察了酶的种类、溶剂、含水量、催化剂量、底物摩尔比和温度等对反应产率的影响,制备了一系列的螺环化合物；研究结果表明,脂肪酶PPL在DMSO中具有最佳的催化活性；4位取代的靛红几乎不能参与反应,氰基乙酰胺或氰基乙酸乙酯代替丙二腈时,也没有检测到产物,说明底物的空间位阻效应显著。
论文发展了核酸酶催化的靛红衍生物和环酮之间的直接不对称aldol加成反应。详细研究了一系列反应条件对催化活性和立体选择性的影响,包括酶的种类、溶剂、水含量、底物摩尔比和底物结构等。结果表明,体系中添加15%去离子水可以提高核酸酶的催化效率和立体选择性,最高分离产率95%,ee值82%,非对映立体选择性dr值为99/1。
论文总共合成了84种化合物,其中15种3,4-二氢吡啶-2-酮衍生物,34种吡啶-2-酮衍生物,12种螺环化合物,12种aldol加成产物,6种α-烷基化腈衍生物,3种烯酮类化合物,1种制备氨基酸中间体和1种p-氨基酸。产物经1H NMR、13C NMR、 FTIR、HRMS等手段表征分析和验证,证实其中56种为新化合物。
As a new tool, biocatalytic synthesis in organic chemistry has attracted lots of attention. In recent years, many enzymes have shown catalytic promiscuity, such as, acylase and protease catalyzed Michael addition, racemase catalyzed the aldol reaction, acylase and transglutaminase catalyzed Henry reaction, and hydrolase accelerated many achievements in terms of enzymatic organic synthesis. However, enzymatic one-pot multicomponent reactions are scarcely reported, especially to synthesize complicated and bioactive heterocycles.
A direct method to construct3,4-dihydropyridin-2-ones by enzymatic condensation of aldehyde with cyanoacetamide and1,3-dicarbonyl compounds was developed. Four new bonds and one six-member aza-ring were formed by one-pot method. Controlled experiments involving catalyst-free, BSA and denatured AA verified the role of active site, its catalytic mechanism was further proposed. And reaction conditions involving hydrolases, solvents, substrate molar ratios, hydrolase loadings and substrate variations were optimized. A series of new compounds based on the3,4-dihydropyridin-2-one core were synthesized.
The Acylase "Amano"(AA)-catalyzed synthesis of valuable pyridin-2-ones via domino Knoevenagel condensation-Michael addition-intramolecular cyclization-oxidization reaction between aldehyde, cyanoacetamide and ethyl acetoacetate or cyclohexyl acetoacetate was also developed by the one-pot strategy. Reaction conditions involving hydrolases, solvents, temperatures, catalyst loadings and substrate variations were investigated. And controlled reaction under nitrogen atmosphere illustrated that pyridin-2-one was formed via the oxidization by oxygen at the final step.
An efficient approach for the synthesis of highly substituted pyridin-2-one derivatives via Acylase "Amano"(AA)-catalyzed three-component reaction between aromatic aldehyde, cyanoacetamide and ketone was proposed. Studies showed that this reaction involved five molecules, which could in situ generate hydrogen donor (3,4-dihydropyridin-2-one) and hydrogen acceptor (Knoevenagel condensation product). The internal transfer hydrogenation process was further confirmed after we quantitatively detected the transforming course of the two intermediates by HPLC; Using this method, pyridin-2-ones and a-alkylated nitriles could be obtained simultaneously, and the a-alkylated nitrile could be transformed to synthetically important β-amino acids via simple conversions in high isolated yield.
A one-pot three-component reaction of isatin derivatives, malononitrile and ketene catalyzed by PPL was established successfully. The effect of enzymes, solvents, water content, catalyst loading, substrate molar ratios and temperatures on reaction yields was investigated in details, and a series of spirocompounds were obtained. PPL exhibited the highest catalytic activity in DMSO. The4-position substituted isatin, cyanoacetamide or ethyl cyanoacetate barely participated in the reaction due to their steric hindrance.
Nuclease p1was observed to directly catalyze the asymmetric aldol reactions between isatin derivatives and cyclic ketones. The effect of a series of reaction conditions involving enzymes, solvents, water contents, substrate molar ratios and substrate structure on yields and stereoselectivities were investigated in details. The addition of15%deionized water had a large influence on the enzyme activity. The isolated yields was up to95%, ee value was up to82%and dr value was up to>99/1.
In this thesis,84compounds were synthesized including15derivatives of3,4-dihydropyridin-2-one,34products of pyridin-2-one,12spirocompounds,12products of aldol addition,6α-alkylated nitrile derivatives,3ketene compounds,1amino acid intermediates and1β-amino acid. These compounds were characterized by1H NMR,13C NMR, FTIR, and HRMS and56compounds have been confirmed to be new compounds.
引文
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