生物催化苊醌及其衍生物不对称还原反应
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摘要
近年来,生物催化的不对称合成反应为人们提供了数量众多的手性化合物,极大地促进了医药、农药、食品及功能材料等领域的的迅速发展,生物催化已经成为一个非常重要的研究方向。
虽然大量文献报道了生物催化脂肪族酮和简单芳香酮羰基的还原反应,但成功实现催化稠环芳酮不对称还原反应报道的则很少。而刚性并具有手性的2-羟基苊酮、1,2-二羟基苊及其衍生物,作为重要的有机合成砌块,在医药中间体、手性金属催化剂和功能材料等精细化学品的合成方面有着十分广泛的应用。为此,本文以苊醌和取代苊醌为底物,利用面包酵母、植物细胞和黄曲霉作为生物催化剂,开展了生物催化苊醌及其衍生物不对称还原反应的研究。
首先,以面包酵母作为催化剂,探讨了催化苊醌不对称还原反应的可行性,针对苊醌难溶于还原反应体系的特点,考察了搅拌方式以及有机助溶剂对还原反应的影响。在此基础上,考察了面包酵母、植物细胞和黄曲霉微生物细胞对苊醌不对称还原反应的催化性能。研究结果表明：1.面包酵母作为催化剂,随着反应的进行,2-羟基苊酮的量先增加后减少,1,2-二羟基苊的含量逐渐增加,当反应进行12h后有明显的增加趋势,48h时含量为95%。此外,通过采用机械搅拌作为动力设备和添加有机助溶剂,可以提高面包酵母催化苊醌还原反应的活性及立体选择性；2.多种植物细胞都可以催化苊醌的还原反应,还原产物只得到2-羟基苊酮,说明植物细胞催化剂与面包酵母催化性能不同,并且不同植物的催化性能差异也较大。在所选择的6种植物中,胡萝卜(根)和桃(果实)细胞对苊醌的立体构型选择性最好,分别得到手性纯度达到81%ee的(-)-2-羟基苊酮和手性纯度达到86%ee的(+)-2-羟基苊酮；3.黑曲霉微生物细胞也可以催化苊醌不对称还原反应。催化还原的过程与面包酵母相似,但催化活性没有面包酵母高。
其次,为了扩大底物的范围,获取更加丰富的手性芳香醇,探讨生物催化苊醌衍生物(5位取代)的不对称还原反应,本文以廉价苊醌为原料,经溴化、硝化、取代、热分解和重氮化等反应,合成了8种苊醌衍生物(5位取代)：5-溴、5-硝基和5-甲氧基、5-叠氮基、5-氨基、5-乙酰胺基、5-氯和5-碘苊醌。以5-溴苊醌和5-甲氧基苊醌为底物,研究了面包酵母催化稠环芳酮的不对称还原反应。结果表明：面包酵母催化还原5-甲氧基苊醌,只生成ee.为55%的2-羟基-6-甲氧基苊酮,没有2-羟基-5-甲氧基苊酮的产物生成,说明面包酵母催化羰基还原的化学选择性很好；使用DMSO作为底物助溶剂,在强烈搅拌下,面包酵母催化还原5-甲氧基苊醌能生成de.为>99%的顺-及反-5-甲氧基-1,2-二羟基苊。
最后,探讨了动物肝细胞对芳香硝基化合物的还原反应。结果表明,大多数动物肝细胞都具有较好的还原活性。在还原Xa模型化合物时：反应进行1h,选择性就达到了最大值,羟胺／胺为71/29；当反应进行到8h,羟胺全部转化为胺,且转化率达到了48%；48h以后,转化率达到了97%以上。在优化的条件下用猪肝细胞还原(Ⅺa-ⅩⅥa)时,随着化合物种类的不同,转化率和选择性表现出了一定的差异,其中Xllla化合物反应4h,转化率只有5%,但选择性却达到了54/46；XVa化合物反应4h,转化率达到了98%,但选择性却只有5/95。
Recently, biocatalysis have provided numerous chiral compounds for greatly promoting the development in the medicine, pesticide, food and functional materials field. Therefore, the biocatalysis has become a very important research area.
It is well documented that most biocatalysts have the ability to reduce the aliphatic ketone and simple aromatic ketone. However, biocatalyst-mediated asymmetric reduction of polycyclic aromatic ketone was rarely. On the other hand, chiral polycyclic aromatic alcohols with rigid structures are widely used as synthetic building blocks for pharmaceuticals intermediates, transition metal ligands, analytical reagents and functional materials. Therefore, in this dissertation, we applied baker's yeast, plant cell and Aspergillus flavus as biocatalyst to mediate the asymmetric reduction of acenaphthenequinone and substituted acenaphthene-qumones.
Firstly, the reasibility of asymmetric reduction of acenaphthenequinone was study using baker's yeast as biocatalyst. In view of the poor solubility of acenaphthenequinone, the effects of the mixing method and organic cosolvent on the reduction were examined. On this basis, the other biocatalysts such as plant cells and aspergillus flavus were also applied to study the asymmetric reduction of acenaphthenequinone. The results showed that:1. Baker's yeast mediated-reduction of the aryl a-diketone gave mono-alcohol and di-alcohol in initial reaction time. The substrate was consumed in the initial4h of reaction time, at the same time, content of mono-alcohol,2-hydroxyacenaphthenone increase in the initial time then decrease. While the content of di-alcohol,1,2-dihydroxyacenaphthene is increasing with the time. When the reaction was performed after12h the trend of increase has a significant improment, and when the reduction proceeded for48h, the content of1,2-dihydroxyacenaphthene reached98%.2. Various plants cell were proven to reduce acenaphthenequinone to afford mono-hydroxyl ketone, exclusively. This results indicated that the plants cell show a different catalytic perfomance with baker's yeast in activity and enantioselectivity. Among the screened six plants cell, the carrot (Daucus carota L.) and Peach (Prunus persica (L.) Batsch.) exhibited high efficiency in preparing hydroxyacenaphthenone, and up to81%ee of (-)-mono-hydroxyl ketone and86%ee of (+)-mono-hydroxyl ketone were obtained.3. Aspergillus Niger can also catalyze the asymmetric reduction of acenaphthenequinone. The reaction process is similar to that of baker's yeast, however, a lower catalytic activity was observed.
Furthermore, to expand the substrate scope of baker's yeast-catalyzed reduction and obtain more valuable chiral aromatic alcohol, eight5-substituted acenaphthenequinones (5-bromo,5-nitro,5-methoxy,5-azido,5-amino,5-acetamido,5-chloro and5-iodo) were synthesized with acenaphthenenquinone as raw material by reaction of bromination, nitration, substitution, thermal decomposition and diazotization. Using5-bromoacenaphthenequinone and5-methoxyacenaphthenequinone as the substrates, the catalytic performance of baker's yeast-mediated asymmetric reduction of polycyclic aromatic ketone was studied. The results show that only2-hydroxy-6-methoxyacenaphthenenone (55%ee) was produced exclusively when5-methoxyacenaphthenequinone as the substrate, which indicated that baker's yeast-mediated reduction of polycyclic aromatic keto shows a good regioselectivity. In the presence of dimethyl sulfoxide (DMSO) as cosolvent and under vigorous agitation, both more than99%ee of cis-and trans-5-methoxy-1,2-dihydroxyacenaphthene were obtained.
Finally, we have performed a study for reductive metabolism of nitroaromatic compounds by several liver microsomes from mammalian, pisces and aves, and found that all of the organisms exhibit the same metabolism process. Among the tested animal's liver microsomes, the pig's liver microsome exhibited the highest reactivity and chemoselectivity. Using4-nitrophthalonitrile (Xa) as substrate, the selectivity was reached the highest and hydroxylamine/amine=71/29when the reaction proceeded for1h. When the reaction proceeded for8h, the hydroxylamine was transformed to corresponding amine compound completely, and the conversion can reached48%. Further prolonging the reaction time up to48h, more than97%of1a was converted. Under the optimized conditions, pig's liver microsome was applied to reduce other nitroaromatic compounds (Ⅺa-ⅩⅥa). There are some differences in the conversion and selectivity along with various substrates. Among them, compound Ⅷa exhibits the lowest reactivity and only5%was converted when the reaction was performed for4h, meanwhile selectivity for hydroxylamine/amine reached54/46. By contrast, compound XVa shows the highest reactivity up to98%conversion, however the selectivity for hydroxylamine reached95%at the same reaction conditions.
虽然大量文献报道了生物催化脂肪族酮和简单芳香酮羰基的还原反应,但成功实现催化稠环芳酮不对称还原反应报道的则很少。而刚性并具有手性的2-羟基苊酮、1,2-二羟基苊及其衍生物,作为重要的有机合成砌块,在医药中间体、手性金属催化剂和功能材料等精细化学品的合成方面有着十分广泛的应用。为此,本文以苊醌和取代苊醌为底物,利用面包酵母、植物细胞和黄曲霉作为生物催化剂,开展了生物催化苊醌及其衍生物不对称还原反应的研究。
首先,以面包酵母作为催化剂,探讨了催化苊醌不对称还原反应的可行性,针对苊醌难溶于还原反应体系的特点,考察了搅拌方式以及有机助溶剂对还原反应的影响。在此基础上,考察了面包酵母、植物细胞和黄曲霉微生物细胞对苊醌不对称还原反应的催化性能。研究结果表明：1.面包酵母作为催化剂,随着反应的进行,2-羟基苊酮的量先增加后减少,1,2-二羟基苊的含量逐渐增加,当反应进行12h后有明显的增加趋势,48h时含量为95%。此外,通过采用机械搅拌作为动力设备和添加有机助溶剂,可以提高面包酵母催化苊醌还原反应的活性及立体选择性；2.多种植物细胞都可以催化苊醌的还原反应,还原产物只得到2-羟基苊酮,说明植物细胞催化剂与面包酵母催化性能不同,并且不同植物的催化性能差异也较大。在所选择的6种植物中,胡萝卜(根)和桃(果实)细胞对苊醌的立体构型选择性最好,分别得到手性纯度达到81%ee的(-)-2-羟基苊酮和手性纯度达到86%ee的(+)-2-羟基苊酮；3.黑曲霉微生物细胞也可以催化苊醌不对称还原反应。催化还原的过程与面包酵母相似,但催化活性没有面包酵母高。
其次,为了扩大底物的范围,获取更加丰富的手性芳香醇,探讨生物催化苊醌衍生物(5位取代)的不对称还原反应,本文以廉价苊醌为原料,经溴化、硝化、取代、热分解和重氮化等反应,合成了8种苊醌衍生物(5位取代)：5-溴、5-硝基和5-甲氧基、5-叠氮基、5-氨基、5-乙酰胺基、5-氯和5-碘苊醌。以5-溴苊醌和5-甲氧基苊醌为底物,研究了面包酵母催化稠环芳酮的不对称还原反应。结果表明：面包酵母催化还原5-甲氧基苊醌,只生成ee.为55%的2-羟基-6-甲氧基苊酮,没有2-羟基-5-甲氧基苊酮的产物生成,说明面包酵母催化羰基还原的化学选择性很好；使用DMSO作为底物助溶剂,在强烈搅拌下,面包酵母催化还原5-甲氧基苊醌能生成de.为>99%的顺-及反-5-甲氧基-1,2-二羟基苊。
最后,探讨了动物肝细胞对芳香硝基化合物的还原反应。结果表明,大多数动物肝细胞都具有较好的还原活性。在还原Xa模型化合物时：反应进行1h,选择性就达到了最大值,羟胺／胺为71/29；当反应进行到8h,羟胺全部转化为胺,且转化率达到了48%；48h以后,转化率达到了97%以上。在优化的条件下用猪肝细胞还原(Ⅺa-ⅩⅥa)时,随着化合物种类的不同,转化率和选择性表现出了一定的差异,其中Xllla化合物反应4h,转化率只有5%,但选择性却达到了54/46；XVa化合物反应4h,转化率达到了98%,但选择性却只有5/95。
Recently, biocatalysis have provided numerous chiral compounds for greatly promoting the development in the medicine, pesticide, food and functional materials field. Therefore, the biocatalysis has become a very important research area.
It is well documented that most biocatalysts have the ability to reduce the aliphatic ketone and simple aromatic ketone. However, biocatalyst-mediated asymmetric reduction of polycyclic aromatic ketone was rarely. On the other hand, chiral polycyclic aromatic alcohols with rigid structures are widely used as synthetic building blocks for pharmaceuticals intermediates, transition metal ligands, analytical reagents and functional materials. Therefore, in this dissertation, we applied baker's yeast, plant cell and Aspergillus flavus as biocatalyst to mediate the asymmetric reduction of acenaphthenequinone and substituted acenaphthene-qumones.
Firstly, the reasibility of asymmetric reduction of acenaphthenequinone was study using baker's yeast as biocatalyst. In view of the poor solubility of acenaphthenequinone, the effects of the mixing method and organic cosolvent on the reduction were examined. On this basis, the other biocatalysts such as plant cells and aspergillus flavus were also applied to study the asymmetric reduction of acenaphthenequinone. The results showed that:1. Baker's yeast mediated-reduction of the aryl a-diketone gave mono-alcohol and di-alcohol in initial reaction time. The substrate was consumed in the initial4h of reaction time, at the same time, content of mono-alcohol,2-hydroxyacenaphthenone increase in the initial time then decrease. While the content of di-alcohol,1,2-dihydroxyacenaphthene is increasing with the time. When the reaction was performed after12h the trend of increase has a significant improment, and when the reduction proceeded for48h, the content of1,2-dihydroxyacenaphthene reached98%.2. Various plants cell were proven to reduce acenaphthenequinone to afford mono-hydroxyl ketone, exclusively. This results indicated that the plants cell show a different catalytic perfomance with baker's yeast in activity and enantioselectivity. Among the screened six plants cell, the carrot (Daucus carota L.) and Peach (Prunus persica (L.) Batsch.) exhibited high efficiency in preparing hydroxyacenaphthenone, and up to81%ee of (-)-mono-hydroxyl ketone and86%ee of (+)-mono-hydroxyl ketone were obtained.3. Aspergillus Niger can also catalyze the asymmetric reduction of acenaphthenequinone. The reaction process is similar to that of baker's yeast, however, a lower catalytic activity was observed.
Furthermore, to expand the substrate scope of baker's yeast-catalyzed reduction and obtain more valuable chiral aromatic alcohol, eight5-substituted acenaphthenequinones (5-bromo,5-nitro,5-methoxy,5-azido,5-amino,5-acetamido,5-chloro and5-iodo) were synthesized with acenaphthenenquinone as raw material by reaction of bromination, nitration, substitution, thermal decomposition and diazotization. Using5-bromoacenaphthenequinone and5-methoxyacenaphthenequinone as the substrates, the catalytic performance of baker's yeast-mediated asymmetric reduction of polycyclic aromatic ketone was studied. The results show that only2-hydroxy-6-methoxyacenaphthenenone (55%ee) was produced exclusively when5-methoxyacenaphthenequinone as the substrate, which indicated that baker's yeast-mediated reduction of polycyclic aromatic keto shows a good regioselectivity. In the presence of dimethyl sulfoxide (DMSO) as cosolvent and under vigorous agitation, both more than99%ee of cis-and trans-5-methoxy-1,2-dihydroxyacenaphthene were obtained.
Finally, we have performed a study for reductive metabolism of nitroaromatic compounds by several liver microsomes from mammalian, pisces and aves, and found that all of the organisms exhibit the same metabolism process. Among the tested animal's liver microsomes, the pig's liver microsome exhibited the highest reactivity and chemoselectivity. Using4-nitrophthalonitrile (Xa) as substrate, the selectivity was reached the highest and hydroxylamine/amine=71/29when the reaction proceeded for1h. When the reaction proceeded for8h, the hydroxylamine was transformed to corresponding amine compound completely, and the conversion can reached48%. Further prolonging the reaction time up to48h, more than97%of1a was converted. Under the optimized conditions, pig's liver microsome was applied to reduce other nitroaromatic compounds (Ⅺa-ⅩⅥa). There are some differences in the conversion and selectivity along with various substrates. Among them, compound Ⅷa exhibits the lowest reactivity and only5%was converted when the reaction was performed for4h, meanwhile selectivity for hydroxylamine/amine reached54/46. By contrast, compound XVa shows the highest reactivity up to98%conversion, however the selectivity for hydroxylamine reached95%at the same reaction conditions.
引文
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