面包酵母催化β-羰基酯类不对称还原研究
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摘要
手性化合物的研究与开发已成为新药研究的热点和方向。具有光学活性的β-羟基酯类化合物是一类重要的化合物,其对映体通常被用来作为有机合成的手性砌块,或作为合成一些天然化合物和药物的中间体。在温和的条件下,利用面包酵母或其他微生物催化β-羰基酯类不对称还原可以得到具有手性的β-羟基酯类化合物。本文主要研究面包酵母催化羰基不对称还原的特点,提高酵母立体选择性的方法及机理,提高酵母的有机溶剂的耐受力,以及考察固定化酵母在水相中催化羰基不对称还原在工业生产上应用的可能性,并且利用呼吸缺陷型酵母考察呼吸链酶对不对称还原的影响。
以乙酰乙酸甲酯为底物,从不同的酵母中筛选出面包酵母作为催化剂,合成(S)-β-羟基丁酸甲酯,考察了反应时间、菌体浓度、辅助底物葡萄糖、缓冲液的pH值、反应温度和底物浓度对反应的影响。结果表明,以面包酵母作催化剂,催化性能良好,较好的反应条件为反应时间4 h,菌体浓度75g/L,葡萄糖浓度为0.6 mol/L,底物浓度0.05 mol/L,pH值为7,温度为35℃。在该条件下,β-羟基丁酸甲酯的收率达57%,选择性达92%。
以乙酰乙酸甲酯为模型底物,利用海藻酸钙胶珠包埋面包酵母,考察了固定化条件和在摇瓶中催化反应的条件,并设计了反应与酵母活性再生相耦合的固定床反应流程。实验结果表明,在合适条件下,用海藻酸钙固定化酵母进行催化产物的e.e.大于99%;经过2个固定床反应器共24批的反应,面包酵母的催化活性可以保持16天,收率可以达到80%,产物的e.e.保持在95%以上。
以乙酰乙酸乙酯为模型底物,以丙烯酸、乙醚、二甲基亚砜、丙烯酰胺、正己烷等有机溶剂选择性地抑制酵母中R型酶,提高反应立体选择性。考察了不同有机溶剂浓度、不同预处理时间对催化能力的影响,结果表明经有机溶剂预处理后可以明显提高反应的立体选择性,能将S型产物的对映体过量值由70%左右提高到85%—98%,其中二甲基亚砜在提高立体选择性的同时,还能保持原有的产物收率,而其他4种有机溶剂的反应收率都有不同程度的下降。并且对3种烯丙基化合物—丙烯酰胺、烯丙基醇、烯丙基溴改变酵母立体选择性的机理进行了研究。结果表明,烯丙基类化合物对细胞及胞内酶系的活性抑制作用具有可逆性,且作用程度大小取决于烯丙基所带基团;细胞内水解酶和线粒体呼吸链酶复合体的活性都有不同程度的下降,琥珀酸脱氢酶或者其亚基可能是催化不对称还原的S型酶。
通过在培养基中逐渐添加有机溶剂驯育得到能够耐受较高有机溶剂浓度的MAA酵母。用此酵母在水相中催化乙酰乙酸甲酯的还原,其得率较普通面包酵母要高。pH和温度对MAA酵母与普通面包都有相同的影响。低底物浓度时,催化4-氯乙酰乙酸乙酯和乙酰乙酸乙酯,同样可以提高反应的收率,但反应的立体选择性下降。但当乙酰乙酸甲酯的浓度达到0.4M时,可以得到相反构型的产物。另外,MAA酵母与面包酵母在形态上相似。
通过诱变,得到了呼吸缺陷型酵母以此来考察呼吸链酶对酵母催化不对称还原反应的影响,发现将呼吸缺陷型酵母用于不对称还原反应,产物的对映体过量值有54%提高到72%;通过对线粒体呼吸链复合体酶活性的研究发现,复合体Ⅰ—Ⅳ的活性下降,表明立体选择性的提高并不一定是呼吸链某种酶活性的改变造成的。结果也表明添加外源电子受体可以增加酵母的生物量但不能提高酵母催化不对称还原的能力。
本文研究的结果对选择和寻找高效率的活细胞催化剂以及研究酵母糖代谢与催化直接的关系有一定的参考价值。
The research and development of chiral compounds has become the hot field and prosperous direction of new drug internationally.β-hydroxy ester with optical activity, whose enantiomer was often used as chiral block in the organic synthesis and intermediate for drug production,was one of the important compounds.β-hydroxy ester having optical activity could be synthesized in asymmetric reduction by baker's yeast or other microorganisms under mild reaction condition.
The main purpose of this work was to study the characteristics of asymmetric reduction catalyzed by baker's yeast,the method to improve stereo-selectivity of the reaction,the tolerance of the yeast to organic solvent,and the possibility to apply immobilized yeast in calcium alginate beads in industrial process. Respiratory-deficient yeast was also used to study the effect of enzyme in respiratory chain on the reaction.
The(S)-methylβ-hydroxybutanoate(MHB)was synthesized from methyl acetoacetate(MAA)by different yeasts in aqueous phase.Effects of reaction time, yeast concentration,glucose concentration,buffer pH,reaction temperature and substrate concentration on both the yield and the stereo-selectivity of(S)-MHB were investigated.The results showed that Baker's yeast effectively catalyzed the reaction. The optimal condition was reaction time 4 h,Baker's yeas 75 g/L,glucose 0.6 mol/L, substrate MAA 0.05 mol/L,pH7,35℃.Under the condition,methylβ-hydroxybutanoate yield and enantiomeric excess(e.e.)57%and 92%,respectively.
Methyl 3-oxobutanoate was chosen as the model substrate,and the condition of immobilization and reaction in flask were investigated in details.A new fixed-bed process,which combined reaction function and cell-activity regeneration,was designed for the asymmetric reduction.The result showed that after immobilized in calcium alginate beads,yeast has high stereo-selectivity:e.e.of the product could achieve 99%under proper condition.Two fixed-bed reactors were able to work steadily for at least 16 days for reaction and regeneration alternately in 2 fixed-beds. The yield could achieve 80%and e.e.could keep above 95%in the fixed beds.
In order to achieve high stereo-selectivity with yeast,ethyl acetoacetate was used as the model substrate,and a novel approach was proposed to selectively inhibit R-enzymes in yeast before reaction.In this method,Baker's yeast was pretreated with acrylic acid,ether,dimethylsulfoxide,acryl amide and hexane,respectively.After the pretreatment with organic solvents,the enantiomeric excess of S-product was raised from 70%to 85%-98%.Among these solvents,dimethylsulfoxide can improve the stereo-selectivity with the original yield while the other 4 solvents decreased the yield to different degrees.The mechanism on alteration of enantioselectivity by allyl compounds added in the reaction system was studied.The results showed that inhibition on enzymes system of yeast by allyl compounds was reversible,and the extent of inhibition was determined by the group linked to the allyl.The activities of intracellular hydrolases and mitochondrial complexes were decreased at different degree,respectively.Succinic acid dehydrogenase or its subunit in the mitochondrial might be the S-enzyme which catalyzes the asymmetric reduction.
By gradually adding low-content of methyl acetoacetate into the solid medium,a new yeast strain,called MAA yeast,was separated from the commercial baker's yeast. The new yeast was used for catalyzing asymmetric reduction of methyl acetoacetate in aqueous phase,and results showed that it was more efficient than the regular baker's yeast in asymmetric reduction of methyl acetoacetate.The influence of external environment,pH and temperature on MAA yeast was as same as baker's yeast.When MAA yeast was used to catalyze other systems,such as reducing ethyl 4-chloro-3-oxobutanoate to ethyl(S)-4-chloro-3- hydroxybutanoate and ethyl acetoacetate to ethyl(S)-3-hydroxybutyrate,the yield also improved at various degrees.In addition,the main product was methyl(S)-β-hydroxybutanoate at low substrate concentration,however,methyl(R)-β-hydroxybutanoate would be produced when the concentration of substrate exceeded 0.4 M.The morphology of the new strain was as same as that of baker's yeast.
By mutagenesis,respiratory-deficient(RD)yeast was prepared to study the effect of enzyme in respiratory chain on the reaction.The e.e.of product catalyzed with RD yeast was improved.The activity of complexesⅠ-Ⅳin mitochondrial were decreased,which means the improvement of e.e.was not caused by change of enzyme activity in respiratory chain.When extraneous electron acceptor was added,the biomass of RD yeast would increase,but no obvious improvement on the effect of asymmetric catalyzation was observed.
以乙酰乙酸甲酯为底物,从不同的酵母中筛选出面包酵母作为催化剂,合成(S)-β-羟基丁酸甲酯,考察了反应时间、菌体浓度、辅助底物葡萄糖、缓冲液的pH值、反应温度和底物浓度对反应的影响。结果表明,以面包酵母作催化剂,催化性能良好,较好的反应条件为反应时间4 h,菌体浓度75g/L,葡萄糖浓度为0.6 mol/L,底物浓度0.05 mol/L,pH值为7,温度为35℃。在该条件下,β-羟基丁酸甲酯的收率达57%,选择性达92%。
以乙酰乙酸甲酯为模型底物,利用海藻酸钙胶珠包埋面包酵母,考察了固定化条件和在摇瓶中催化反应的条件,并设计了反应与酵母活性再生相耦合的固定床反应流程。实验结果表明,在合适条件下,用海藻酸钙固定化酵母进行催化产物的e.e.大于99%;经过2个固定床反应器共24批的反应,面包酵母的催化活性可以保持16天,收率可以达到80%,产物的e.e.保持在95%以上。
以乙酰乙酸乙酯为模型底物,以丙烯酸、乙醚、二甲基亚砜、丙烯酰胺、正己烷等有机溶剂选择性地抑制酵母中R型酶,提高反应立体选择性。考察了不同有机溶剂浓度、不同预处理时间对催化能力的影响,结果表明经有机溶剂预处理后可以明显提高反应的立体选择性,能将S型产物的对映体过量值由70%左右提高到85%—98%,其中二甲基亚砜在提高立体选择性的同时,还能保持原有的产物收率,而其他4种有机溶剂的反应收率都有不同程度的下降。并且对3种烯丙基化合物—丙烯酰胺、烯丙基醇、烯丙基溴改变酵母立体选择性的机理进行了研究。结果表明,烯丙基类化合物对细胞及胞内酶系的活性抑制作用具有可逆性,且作用程度大小取决于烯丙基所带基团;细胞内水解酶和线粒体呼吸链酶复合体的活性都有不同程度的下降,琥珀酸脱氢酶或者其亚基可能是催化不对称还原的S型酶。
通过在培养基中逐渐添加有机溶剂驯育得到能够耐受较高有机溶剂浓度的MAA酵母。用此酵母在水相中催化乙酰乙酸甲酯的还原,其得率较普通面包酵母要高。pH和温度对MAA酵母与普通面包都有相同的影响。低底物浓度时,催化4-氯乙酰乙酸乙酯和乙酰乙酸乙酯,同样可以提高反应的收率,但反应的立体选择性下降。但当乙酰乙酸甲酯的浓度达到0.4M时,可以得到相反构型的产物。另外,MAA酵母与面包酵母在形态上相似。
通过诱变,得到了呼吸缺陷型酵母以此来考察呼吸链酶对酵母催化不对称还原反应的影响,发现将呼吸缺陷型酵母用于不对称还原反应,产物的对映体过量值有54%提高到72%;通过对线粒体呼吸链复合体酶活性的研究发现,复合体Ⅰ—Ⅳ的活性下降,表明立体选择性的提高并不一定是呼吸链某种酶活性的改变造成的。结果也表明添加外源电子受体可以增加酵母的生物量但不能提高酵母催化不对称还原的能力。
本文研究的结果对选择和寻找高效率的活细胞催化剂以及研究酵母糖代谢与催化直接的关系有一定的参考价值。
The research and development of chiral compounds has become the hot field and prosperous direction of new drug internationally.β-hydroxy ester with optical activity, whose enantiomer was often used as chiral block in the organic synthesis and intermediate for drug production,was one of the important compounds.β-hydroxy ester having optical activity could be synthesized in asymmetric reduction by baker's yeast or other microorganisms under mild reaction condition.
The main purpose of this work was to study the characteristics of asymmetric reduction catalyzed by baker's yeast,the method to improve stereo-selectivity of the reaction,the tolerance of the yeast to organic solvent,and the possibility to apply immobilized yeast in calcium alginate beads in industrial process. Respiratory-deficient yeast was also used to study the effect of enzyme in respiratory chain on the reaction.
The(S)-methylβ-hydroxybutanoate(MHB)was synthesized from methyl acetoacetate(MAA)by different yeasts in aqueous phase.Effects of reaction time, yeast concentration,glucose concentration,buffer pH,reaction temperature and substrate concentration on both the yield and the stereo-selectivity of(S)-MHB were investigated.The results showed that Baker's yeast effectively catalyzed the reaction. The optimal condition was reaction time 4 h,Baker's yeas 75 g/L,glucose 0.6 mol/L, substrate MAA 0.05 mol/L,pH7,35℃.Under the condition,methylβ-hydroxybutanoate yield and enantiomeric excess(e.e.)57%and 92%,respectively.
Methyl 3-oxobutanoate was chosen as the model substrate,and the condition of immobilization and reaction in flask were investigated in details.A new fixed-bed process,which combined reaction function and cell-activity regeneration,was designed for the asymmetric reduction.The result showed that after immobilized in calcium alginate beads,yeast has high stereo-selectivity:e.e.of the product could achieve 99%under proper condition.Two fixed-bed reactors were able to work steadily for at least 16 days for reaction and regeneration alternately in 2 fixed-beds. The yield could achieve 80%and e.e.could keep above 95%in the fixed beds.
In order to achieve high stereo-selectivity with yeast,ethyl acetoacetate was used as the model substrate,and a novel approach was proposed to selectively inhibit R-enzymes in yeast before reaction.In this method,Baker's yeast was pretreated with acrylic acid,ether,dimethylsulfoxide,acryl amide and hexane,respectively.After the pretreatment with organic solvents,the enantiomeric excess of S-product was raised from 70%to 85%-98%.Among these solvents,dimethylsulfoxide can improve the stereo-selectivity with the original yield while the other 4 solvents decreased the yield to different degrees.The mechanism on alteration of enantioselectivity by allyl compounds added in the reaction system was studied.The results showed that inhibition on enzymes system of yeast by allyl compounds was reversible,and the extent of inhibition was determined by the group linked to the allyl.The activities of intracellular hydrolases and mitochondrial complexes were decreased at different degree,respectively.Succinic acid dehydrogenase or its subunit in the mitochondrial might be the S-enzyme which catalyzes the asymmetric reduction.
By gradually adding low-content of methyl acetoacetate into the solid medium,a new yeast strain,called MAA yeast,was separated from the commercial baker's yeast. The new yeast was used for catalyzing asymmetric reduction of methyl acetoacetate in aqueous phase,and results showed that it was more efficient than the regular baker's yeast in asymmetric reduction of methyl acetoacetate.The influence of external environment,pH and temperature on MAA yeast was as same as baker's yeast.When MAA yeast was used to catalyze other systems,such as reducing ethyl 4-chloro-3-oxobutanoate to ethyl(S)-4-chloro-3- hydroxybutanoate and ethyl acetoacetate to ethyl(S)-3-hydroxybutyrate,the yield also improved at various degrees.In addition,the main product was methyl(S)-β-hydroxybutanoate at low substrate concentration,however,methyl(R)-β-hydroxybutanoate would be produced when the concentration of substrate exceeded 0.4 M.The morphology of the new strain was as same as that of baker's yeast.
By mutagenesis,respiratory-deficient(RD)yeast was prepared to study the effect of enzyme in respiratory chain on the reaction.The e.e.of product catalyzed with RD yeast was improved.The activity of complexesⅠ-Ⅳin mitochondrial were decreased,which means the improvement of e.e.was not caused by change of enzyme activity in respiratory chain.When extraneous electron acceptor was added,the biomass of RD yeast would increase,but no obvious improvement on the effect of asymmetric catalyzation was observed.
引文
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