毕赤酵母细胞展示的CALB脂肪酶的表征及非水相催化特性研究
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摘要
南极假丝酵母脂肪酶B (Candida antarctica lipase B，CALB)在酯化、转酯、手性拆分等非水相催化反应中表现出比其他脂肪酶更出色的催化活性。利用表面展示技术将脂肪酶锚定在细胞表面，类似于酶的固定化。通过发酵得到大量细胞，冻干即可用于催化，无需酶的提取纯化，杜绝了酶在固定化过程中的损失并节省了成本。然而，关于展示脂肪酶非水相催化特性，尚未见比较系统的研究，阻碍了展示脂肪酶在非水催化领域的应用。基于上述情况，本论文选取毕赤酵母细胞展示的CALB作为研究对象，将其应用于催化多种类型的反应以研究其非水相催化特性。针对亲水酵母细胞与疏水底物接触受阻的问题，对展示脂肪酶的表面进行疏水性修饰，探讨展示脂肪酶表面性质对非水相催化特性的影响。具体研究内容及结果如下：
(1)细胞表面展示脂肪酶的定量
合成脂肪酶的不可逆抑制剂4-甲基伞形酮己基膦酸酯，该物质与酵母细胞展示脂肪酶的活性中心不可逆结合并释放荧光物质4-甲基伞形酮(4-MU)，通过测定4-MU的含量可以计算脂肪酶的活性中心数目。该方法精确灵敏，重现性好，与酶活测定和免疫荧光反应的结果具有较好的相关性。用该方法测得毕赤酵母展示CALB的载酶量为5‰。
(2)毕赤酵母细胞展示CALB催化合成芳香酯
研究了毕赤酵母展示CALB的底物选择性，酵母细胞的亲水性改变了展示CALB对直链醇的选择性，而底物的空间位阻效应是影响催化效率的首要因素。考察了溶剂、温度、底物浓度和摩尔比、细胞添加量对展示脂肪酶催化合成乙酸酯反应的影响，发现其具有较好的溶剂耐受性和温度耐受性。反应动力学研究显示毕赤酵母展示CALB对乙酸的耐受程度强于商品酶Novozym435。在此基础上，设计5L搅拌式反应器并合成了10种芳香酯。为了进一步探讨绿色制造的可能性，将展示CALB应用于30L无溶剂体系合成己酸乙酯，底物转化率达到90%。
(3)毕赤酵母细胞展示CALB催化合成生物柴油
在毕赤酵母展示RML催化合成生物柴油的反应中，加入适量毕赤酵母展示的CALB，可以消除反应的限速步骤，提高转酯合成效率。此外，使用异辛烷-叔丁醇混合溶剂能有效地改善细胞对甘油吸附效应，促进展示脂肪酶的分散。使用包括废油在内的各种原料合成生物柴油，12h甲酯产率达到90%。连续反应20批次后，甲酯的相对产率仍在85%以上。
(4)毕赤酵母细胞展示CALB催化区域选择性和手性选择性反应
毕赤酵母展示CALB催化葡萄糖与月桂酸合成葡萄糖月桂酸单酯，催化果糖与月桂酸合成果糖月桂酸单酯/二酯，核磁共振检测产物的结构表明展示CALB对糖环上的伯羟基具有特异选择性。将展示CALB应用于拆分-苯乙醇，显示只有R型底物才能被催化，但不能拆分手性碳原子附近有较大空间位阻基团的底物，如药物班布特罗。
(5)毕赤酵母细胞展示CALB的表面疏水修饰
通过在毕赤酵母细胞表面共展示真菌疏水蛋白HFBI、吸附表面活性剂Tween80、吸附离子液体[Omin][PF6]和添加疏水性碳源四种方法分别对毕赤酵母展示CALB进行表面疏水修饰。对修饰后的酶进行表面疏水性分析以及表面基团表征，发现四种修饰方法都能不同程度地增强毕赤酵母展示CALB的疏水性，吸附Tween80和[Omin][PF6]对表面疏水性的增强程度较大。将修饰后的酶应用于合成己酸乙酯、长链脂肪酸乙酯和生物柴油，疏水性强的展示CALB催化效率较高。
本论文通过研究毕赤酵母展示CALB催化多个反应，较为系统地阐明了展示酶作为一种特殊形式的固定化酶在非水相中的催化特性。初步探索了改善展示脂肪酶表面性质的方法，为其进一步的非水相催化应用提供基础。
Candida antarctica lipase B (CALB) exhibit better catalytic activity than the otherlipases in the esterification, hydrolysis, transesterification, as well as other types of reactions.Analogous to conventional enzyme immobilization, the display of lipases can be consideredas a type of self-immobilization on cell wall by connected to a anchoring protein. Suchlipase-displaying yeast cells can be produced during a high density fermentation, and afterlyophilization, the cells can be directly uesd as biocatalyst without enzyme purification step.So this procedure prevents the enzyme loss during immobilization process and saves cost.However, little has been known about catalytic characteristics of displayed lipases innon-aqueous phase. In this work, the CALB-displaying Pichia pastoris whole-cells were usedto catalyze various reactions. Substrate selectivity, solvent tolerance and reaction kineticswere discussed to determine the catalytic characteristics of CALB-displaying P. pastoris cellsin non-aqueous phase. The relationship between cell surface characteristics and catalyticsynthesis efficiency was also investigated by cell surface modification. Specific contents andresults are as follows:
(1) Quantificationof the enzyme displayed on cell surface
Lipase irreversible inhibitor4-methylumbelliferyl hexylphosphonate (4-MUHP), whichcan irreversiblely bind with the lipase activity site and release a fluorescent substance4-methylumbelliferyl (4-MU) is synthesized. By determination of4-MU amount, the number oflipase active site can be calculated. This method is accurate, sensitive and in good agreementwith hydrolysis activity and synthesis activity and is a powerful tool to evaluate thecharacteristics of CALB-displaying cells used as immobilized enzyme.
(2) Synthesis of flavor esters catalyzed by CALB-displaying P. pastoris cells
CALB-displaying P. pastoris cells were used to catalyze synthesis of short-chain flavoresters in non-aqueous phase. The study of substrate selectivity indicated that hindrance ofbranched and large group was the most important factor. Effects of solvent, temperature,substrate concentration, substrate molar ratio and cells dosage on esterification wereinvestigated and the results showed CALB-displaying P. pastoris cells were good tolerancefor high substrates concentration, especially strong polar substrates. Based on these results, 10flavor esters were successfully synthesized in5L stirred reactor. Solvent-free synthesis ofethyl caproate was also achieved in a50L pilot reactor and the conversion rate reached90%.
(3) Synthesis of biodiesel catalyzed by lipase-displaying P. pastoris cells
The combined utilization of CALB and RML, separately displayed on P. pastoris cells,to produce biodiesel in co-solvent media was investigated. The synergistic effect of the twodisplayed lipases was to elimination of the rate-limiting step. The use of tert-butanol andisooctane as the co-solvent media was found to reduce the adsorption of glycerol onto cells.Scaled-up reactions using various types of feedstock were carried out in a0.5L stirred reactorunder optimum conditions, affording methyl ester yields over90%in12h. Moreover, themethyl ester yields remained above85%after20repeated batch cycles.
(4) Regioselective synthesis and enantioselective resolution catalyzed by CALB-displaying cells
CALB-displaying P. pastoris cells were used to catalyze the synthesis of glucose laurateand fructose laurate (mono-ester and di-ester). NMR detection of sugar ester shoued thatCALB exhibited specific selectivity for primary hydroxyl groups. CALB-displayingP.pastoris showed excellent R-enantioselectivity to-phenylethanol. However, poor substrateand product enantiomer excess values were obtained when catalyzing enantioselectiveresolution of bambuterol.
(5) Surface hydrophobicity modification of CALB-displaying P. pastoris cells
Fungal hydrophobin proteins HFBI, surfactant Tween80, ionic liquid [Omin][PF6], andhydrophobic carbon source were used to modify surface hydrophobicity of CALB-displayingP. pastoris cells. The CALB loading and hydrophobicity of modified cells were detectied; thechange of cell surface groups was characterized using Fourier transform IR. It was found thatfour modification methods had enhanced hydrophobicity of cell surface, Tween80and [Omin][PF6] absorbed on cell surface showed better enhancement. The modified cells were used tosynthesis of ethyl caproate, long-chain fatty acid ethyl ester and biodiesel, the catalyticefficiency were improved, especially for Tween80and [Omin][PF6]–modified cells.
In this work, various types of reactions catalyzed by CALB-displaying P. pastoris cellshave been investigated to illustrate the catalytic properties of this biocatalyst whichperformed as a special form of immobilized enzyme in non-aqueous phase. The method to improve the cell surface properties was development, this may provide a reference forenzyme-displaying cells’ potential applications.
(1)细胞表面展示脂肪酶的定量
合成脂肪酶的不可逆抑制剂4-甲基伞形酮己基膦酸酯，该物质与酵母细胞展示脂肪酶的活性中心不可逆结合并释放荧光物质4-甲基伞形酮(4-MU)，通过测定4-MU的含量可以计算脂肪酶的活性中心数目。该方法精确灵敏，重现性好，与酶活测定和免疫荧光反应的结果具有较好的相关性。用该方法测得毕赤酵母展示CALB的载酶量为5‰。
(2)毕赤酵母细胞展示CALB催化合成芳香酯
研究了毕赤酵母展示CALB的底物选择性，酵母细胞的亲水性改变了展示CALB对直链醇的选择性，而底物的空间位阻效应是影响催化效率的首要因素。考察了溶剂、温度、底物浓度和摩尔比、细胞添加量对展示脂肪酶催化合成乙酸酯反应的影响，发现其具有较好的溶剂耐受性和温度耐受性。反应动力学研究显示毕赤酵母展示CALB对乙酸的耐受程度强于商品酶Novozym435。在此基础上，设计5L搅拌式反应器并合成了10种芳香酯。为了进一步探讨绿色制造的可能性，将展示CALB应用于30L无溶剂体系合成己酸乙酯，底物转化率达到90%。
(3)毕赤酵母细胞展示CALB催化合成生物柴油
在毕赤酵母展示RML催化合成生物柴油的反应中，加入适量毕赤酵母展示的CALB，可以消除反应的限速步骤，提高转酯合成效率。此外，使用异辛烷-叔丁醇混合溶剂能有效地改善细胞对甘油吸附效应，促进展示脂肪酶的分散。使用包括废油在内的各种原料合成生物柴油，12h甲酯产率达到90%。连续反应20批次后，甲酯的相对产率仍在85%以上。
(4)毕赤酵母细胞展示CALB催化区域选择性和手性选择性反应
毕赤酵母展示CALB催化葡萄糖与月桂酸合成葡萄糖月桂酸单酯，催化果糖与月桂酸合成果糖月桂酸单酯/二酯，核磁共振检测产物的结构表明展示CALB对糖环上的伯羟基具有特异选择性。将展示CALB应用于拆分-苯乙醇，显示只有R型底物才能被催化，但不能拆分手性碳原子附近有较大空间位阻基团的底物，如药物班布特罗。
(5)毕赤酵母细胞展示CALB的表面疏水修饰
通过在毕赤酵母细胞表面共展示真菌疏水蛋白HFBI、吸附表面活性剂Tween80、吸附离子液体[Omin][PF6]和添加疏水性碳源四种方法分别对毕赤酵母展示CALB进行表面疏水修饰。对修饰后的酶进行表面疏水性分析以及表面基团表征，发现四种修饰方法都能不同程度地增强毕赤酵母展示CALB的疏水性，吸附Tween80和[Omin][PF6]对表面疏水性的增强程度较大。将修饰后的酶应用于合成己酸乙酯、长链脂肪酸乙酯和生物柴油，疏水性强的展示CALB催化效率较高。
本论文通过研究毕赤酵母展示CALB催化多个反应，较为系统地阐明了展示酶作为一种特殊形式的固定化酶在非水相中的催化特性。初步探索了改善展示脂肪酶表面性质的方法，为其进一步的非水相催化应用提供基础。
Candida antarctica lipase B (CALB) exhibit better catalytic activity than the otherlipases in the esterification, hydrolysis, transesterification, as well as other types of reactions.Analogous to conventional enzyme immobilization, the display of lipases can be consideredas a type of self-immobilization on cell wall by connected to a anchoring protein. Suchlipase-displaying yeast cells can be produced during a high density fermentation, and afterlyophilization, the cells can be directly uesd as biocatalyst without enzyme purification step.So this procedure prevents the enzyme loss during immobilization process and saves cost.However, little has been known about catalytic characteristics of displayed lipases innon-aqueous phase. In this work, the CALB-displaying Pichia pastoris whole-cells were usedto catalyze various reactions. Substrate selectivity, solvent tolerance and reaction kineticswere discussed to determine the catalytic characteristics of CALB-displaying P. pastoris cellsin non-aqueous phase. The relationship between cell surface characteristics and catalyticsynthesis efficiency was also investigated by cell surface modification. Specific contents andresults are as follows:
(1) Quantificationof the enzyme displayed on cell surface
Lipase irreversible inhibitor4-methylumbelliferyl hexylphosphonate (4-MUHP), whichcan irreversiblely bind with the lipase activity site and release a fluorescent substance4-methylumbelliferyl (4-MU) is synthesized. By determination of4-MU amount, the number oflipase active site can be calculated. This method is accurate, sensitive and in good agreementwith hydrolysis activity and synthesis activity and is a powerful tool to evaluate thecharacteristics of CALB-displaying cells used as immobilized enzyme.
(2) Synthesis of flavor esters catalyzed by CALB-displaying P. pastoris cells
CALB-displaying P. pastoris cells were used to catalyze synthesis of short-chain flavoresters in non-aqueous phase. The study of substrate selectivity indicated that hindrance ofbranched and large group was the most important factor. Effects of solvent, temperature,substrate concentration, substrate molar ratio and cells dosage on esterification wereinvestigated and the results showed CALB-displaying P. pastoris cells were good tolerancefor high substrates concentration, especially strong polar substrates. Based on these results, 10flavor esters were successfully synthesized in5L stirred reactor. Solvent-free synthesis ofethyl caproate was also achieved in a50L pilot reactor and the conversion rate reached90%.
(3) Synthesis of biodiesel catalyzed by lipase-displaying P. pastoris cells
The combined utilization of CALB and RML, separately displayed on P. pastoris cells,to produce biodiesel in co-solvent media was investigated. The synergistic effect of the twodisplayed lipases was to elimination of the rate-limiting step. The use of tert-butanol andisooctane as the co-solvent media was found to reduce the adsorption of glycerol onto cells.Scaled-up reactions using various types of feedstock were carried out in a0.5L stirred reactorunder optimum conditions, affording methyl ester yields over90%in12h. Moreover, themethyl ester yields remained above85%after20repeated batch cycles.
(4) Regioselective synthesis and enantioselective resolution catalyzed by CALB-displaying cells
CALB-displaying P. pastoris cells were used to catalyze the synthesis of glucose laurateand fructose laurate (mono-ester and di-ester). NMR detection of sugar ester shoued thatCALB exhibited specific selectivity for primary hydroxyl groups. CALB-displayingP.pastoris showed excellent R-enantioselectivity to-phenylethanol. However, poor substrateand product enantiomer excess values were obtained when catalyzing enantioselectiveresolution of bambuterol.
(5) Surface hydrophobicity modification of CALB-displaying P. pastoris cells
Fungal hydrophobin proteins HFBI, surfactant Tween80, ionic liquid [Omin][PF6], andhydrophobic carbon source were used to modify surface hydrophobicity of CALB-displayingP. pastoris cells. The CALB loading and hydrophobicity of modified cells were detectied; thechange of cell surface groups was characterized using Fourier transform IR. It was found thatfour modification methods had enhanced hydrophobicity of cell surface, Tween80and [Omin][PF6] absorbed on cell surface showed better enhancement. The modified cells were used tosynthesis of ethyl caproate, long-chain fatty acid ethyl ester and biodiesel, the catalyticefficiency were improved, especially for Tween80and [Omin][PF6]–modified cells.
In this work, various types of reactions catalyzed by CALB-displaying P. pastoris cellshave been investigated to illustrate the catalytic properties of this biocatalyst whichperformed as a special form of immobilized enzyme in non-aqueous phase. The method to improve the cell surface properties was development, this may provide a reference forenzyme-displaying cells’ potential applications.
引文
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