无溶剂体系固定化磷脂酶Lecitase~（？）Ultra催化合成甘油二酯研究
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摘要
甘油二酯（DAG）是近年来倍受关注的一种功能性油脂，可降低餐后血脂水平和抑制食欲，具有控制体重和防止肥胖症等功效。众多动物试验和人体试验结果表明，以DAG为食用油，安全可靠，不会带来健康问题和负面影响。目前DAG的酶法制备多采用脂肪酶催化，价格高，工业化成本较高。本论文研究了无溶剂体系磷脂酶Lecitase~(?) Ultra催化合成DAG的方法，基于工业化的考虑，对该酶进行固定化，便于重复使用，设计开发了新型鼓泡式反应器，将其用于固定化酶的催化反应，制备了高纯度DAG，并应用于搅打稀奶油中，为磷脂酶Lecitase~(?) Ultra的开发利用和DAG的制备提供理论和方法的指导。论文主要研究内容和结果如下：
1、研究了游离磷脂酶Lecitase~(?) Ultra催化油酸和甘油直接酯化法合成1,3-DAG，考察了有机溶剂和无溶剂体系的反应效果，对无溶剂体系中的合成工艺进行优化。发现该酶在无溶剂体系中可实现DAG的快速酯化合成，仅1.5h反应，油酸酯化率达80.3%，产物中1,3-DAG含量为54.8wt%。
2、研究了磷脂酶Lecitase~(?) Ultra的吸附法固定化条件，发现大孔树脂DA-201为最佳载体，得到固定化磷脂酶Lecitase~(?) Ultra（IM-LU）酶活为1652.4U/g。吸附动力学研究表明Langmuir方程可较好地描述该吸附过程，为单层吸附。经固定化后，磷脂酶的Km增大，Vmax减小，酶的热、pH、金属离子和储藏稳定性都有所提高。FTIR测定结果显示，经固定化过程，酶分子的二级结构稍有改变，其α-螺旋含量减少，β-折叠增多。
3、研究了无溶剂体系IM-LU催化大豆油甘油解制备DAG的反应效果，对底物摩尔比、温度、加酶量等反应条件进行了优化，经12h反应，产物中DAG含量为53.7wt%。磷脂酶催化大豆油甘油解反应具有1,3-位点选择性，固定化过程未改变这一特性。与原料大豆油相比，DAG中饱和脂肪酸得到富集，亚油酸含量显著降低，油酸含量有一定升高。
4、设计试制了新型鼓泡式反应器（BCR），将其用于IM-LU催化酯化合成1,3-DAG。与搅拌式反应器相比，BCR可节约酶制剂用量并加快反应进程，得到了快速合成1,3-DAG的工艺条件，经45min反应，酯化率达86.4%。在BCR中，酯化速度和酯化率明显提高，产物1,3-DAG含量为58.3wt%。BCR可避免因机械搅拌导致固定化酶的剪切失活，提高酶的操作稳定性。
5、通过分子蒸馏制备高纯度DAG油，研究了其熔化结晶性能、固体脂肪含量和脂肪酸组成，并替代氢化植物油BL-39用于搅打稀奶油中。结果发现，随着DAG替代量的升高，搅打稀奶油的平均粒径大小、界面蛋白含量、脂肪部分聚结率和质构特性值等呈上升的变化趋势。5%–15%DAG替代量可缩短搅打时间，提高搅打稀奶油的站立稳定性，与对照样相比，其感官品质变化不大。20%以上替代量样品的站立稳定性和感官品质均较差，不宜用于本文的搅打稀奶油中。
Diacylglycerol (DAG), a functional lipid, has attracted a lot of attentions in recent years.It has several advantages, such as reducing the level of postprandial blood lipid, inhibitingappetite, controlling body weight and preventing obesity. Results from animal tests andhuman trials show that, as an edible oil, DAG is safe and does not bring health problems andnegative effects. Currently, DAG has been prepared through enzymatic method catalyzed bylipase, which is expensive for industrial application. In the present study, DAG wassynthesized catalyzed by phospholipase Lecitase~(?) Ultra in a solvent-free system. Based onpractical application consideration, Lecitase~(?) Ultra was immobilized for easily recycling usein this study. A novel enzyme reactor was developed and employed for enzymatic reactions.DAG with high purity was produced and applied in whipped cream. The new findings of thiswork will be useful for utilization of Lecitase~(?) Ultra as well as preparation of DAG-enrichedoil. The main research contents and results are as follows:
1. In this work,1,3-DAG was synthesized through direct esterification reaction of oleicacid and glycerol catalyzed by Lecitase~(?) Ultra. The reactions in organic solvents system andsolvent-free system were examined, and the latter was selected. The reaction conditions insolvent-free system were optimized. The esterification efficiency was80.3%after1.5hreaction. The1,3-DAG content in product was determined as54.8wt%.
2. Lecitase~(?) Ultra was immobilized onto macroporous resin DA-201via adsorptionmethod. The immobilized Lecitase~(?) Ultra (IM-LU) was obtained with a lipase activity of1652.4U/g. Langmuir equation was fit to describe this adsorption process, which was foundas a monolayer adsorption mechanism. After immobilization, the Kmof enzyme increased andVmaxdecreased. The thermal, pH and storage stability were all improved. The FTIR resultshowed that the secondary structure of enzyme had changed to some extent afterimmobilization. The content of α-helix decreased, and that of β-sheet increased.
3. DAG was prepared through glycerolysis of soybean oil catalyzed by IM-LU in asolvent-free system. The reaction conditions were investigated containing mole ratio ofsubstrates, temperature, enzyme load, and so forth. With12h reaction, DAG content inproduct was53.7wt%. Both free Lecitase~(?) Ultra and IM-LU had1,3-regioselective property on soybean oil. Compared with the original oil, the saturated fatty acids in DAG wereenriched. The content of linoleic acid decreased significantly, and the content of oleic acidincreased to some extent.
4. A novel bubble column reactor (BCR) was trial-manufactured and applied forenzymatic esterification to produce1,3-DAG. Compared with stirred tank reactor, the load ofIM-LU was reduced and the reaction was accelerated. After45min reaction, the esterificationefficiency was86.4%and the1,3-DAG content was58.3wt%. The BCR can avoid the shearinactivation of immobilized enzyme due to mechanical agitation. The stability of the enzymewas improved.
5. DAG-enriched oil was prepared by molecular distillation. Its melting andcrystallization properties, solid fat content and fatty acid composition were investigated. TheDAG oil was used to substitute hydrogenated vegetable oil BL-39in whipped cream. Theresult showed that with the DAG substitution increasing, the average particle size, surfaceprotein concentration, partial coalescence of fat and textural property values of whippedcream increased. DAG substitution of5%–15%could shorten the whipping time and improvethe standing stability. And the organoleptic property had not changed much as compared withthe control. Sample with20%DAG substitution exhibited weak standing stability andorganoleptic property. As a result, it was inappropriate to be applied in whipped cream in thepresent study.
1、研究了游离磷脂酶Lecitase~(?) Ultra催化油酸和甘油直接酯化法合成1,3-DAG，考察了有机溶剂和无溶剂体系的反应效果，对无溶剂体系中的合成工艺进行优化。发现该酶在无溶剂体系中可实现DAG的快速酯化合成，仅1.5h反应，油酸酯化率达80.3%，产物中1,3-DAG含量为54.8wt%。
2、研究了磷脂酶Lecitase~(?) Ultra的吸附法固定化条件，发现大孔树脂DA-201为最佳载体，得到固定化磷脂酶Lecitase~(?) Ultra（IM-LU）酶活为1652.4U/g。吸附动力学研究表明Langmuir方程可较好地描述该吸附过程，为单层吸附。经固定化后，磷脂酶的Km增大，Vmax减小，酶的热、pH、金属离子和储藏稳定性都有所提高。FTIR测定结果显示，经固定化过程，酶分子的二级结构稍有改变，其α-螺旋含量减少，β-折叠增多。
3、研究了无溶剂体系IM-LU催化大豆油甘油解制备DAG的反应效果，对底物摩尔比、温度、加酶量等反应条件进行了优化，经12h反应，产物中DAG含量为53.7wt%。磷脂酶催化大豆油甘油解反应具有1,3-位点选择性，固定化过程未改变这一特性。与原料大豆油相比，DAG中饱和脂肪酸得到富集，亚油酸含量显著降低，油酸含量有一定升高。
4、设计试制了新型鼓泡式反应器（BCR），将其用于IM-LU催化酯化合成1,3-DAG。与搅拌式反应器相比，BCR可节约酶制剂用量并加快反应进程，得到了快速合成1,3-DAG的工艺条件，经45min反应，酯化率达86.4%。在BCR中，酯化速度和酯化率明显提高，产物1,3-DAG含量为58.3wt%。BCR可避免因机械搅拌导致固定化酶的剪切失活，提高酶的操作稳定性。
5、通过分子蒸馏制备高纯度DAG油，研究了其熔化结晶性能、固体脂肪含量和脂肪酸组成，并替代氢化植物油BL-39用于搅打稀奶油中。结果发现，随着DAG替代量的升高，搅打稀奶油的平均粒径大小、界面蛋白含量、脂肪部分聚结率和质构特性值等呈上升的变化趋势。5%–15%DAG替代量可缩短搅打时间，提高搅打稀奶油的站立稳定性，与对照样相比，其感官品质变化不大。20%以上替代量样品的站立稳定性和感官品质均较差，不宜用于本文的搅打稀奶油中。
Diacylglycerol (DAG), a functional lipid, has attracted a lot of attentions in recent years.It has several advantages, such as reducing the level of postprandial blood lipid, inhibitingappetite, controlling body weight and preventing obesity. Results from animal tests andhuman trials show that, as an edible oil, DAG is safe and does not bring health problems andnegative effects. Currently, DAG has been prepared through enzymatic method catalyzed bylipase, which is expensive for industrial application. In the present study, DAG wassynthesized catalyzed by phospholipase Lecitase~(?) Ultra in a solvent-free system. Based onpractical application consideration, Lecitase~(?) Ultra was immobilized for easily recycling usein this study. A novel enzyme reactor was developed and employed for enzymatic reactions.DAG with high purity was produced and applied in whipped cream. The new findings of thiswork will be useful for utilization of Lecitase~(?) Ultra as well as preparation of DAG-enrichedoil. The main research contents and results are as follows:
1. In this work,1,3-DAG was synthesized through direct esterification reaction of oleicacid and glycerol catalyzed by Lecitase~(?) Ultra. The reactions in organic solvents system andsolvent-free system were examined, and the latter was selected. The reaction conditions insolvent-free system were optimized. The esterification efficiency was80.3%after1.5hreaction. The1,3-DAG content in product was determined as54.8wt%.
2. Lecitase~(?) Ultra was immobilized onto macroporous resin DA-201via adsorptionmethod. The immobilized Lecitase~(?) Ultra (IM-LU) was obtained with a lipase activity of1652.4U/g. Langmuir equation was fit to describe this adsorption process, which was foundas a monolayer adsorption mechanism. After immobilization, the Kmof enzyme increased andVmaxdecreased. The thermal, pH and storage stability were all improved. The FTIR resultshowed that the secondary structure of enzyme had changed to some extent afterimmobilization. The content of α-helix decreased, and that of β-sheet increased.
3. DAG was prepared through glycerolysis of soybean oil catalyzed by IM-LU in asolvent-free system. The reaction conditions were investigated containing mole ratio ofsubstrates, temperature, enzyme load, and so forth. With12h reaction, DAG content inproduct was53.7wt%. Both free Lecitase~(?) Ultra and IM-LU had1,3-regioselective property on soybean oil. Compared with the original oil, the saturated fatty acids in DAG wereenriched. The content of linoleic acid decreased significantly, and the content of oleic acidincreased to some extent.
4. A novel bubble column reactor (BCR) was trial-manufactured and applied forenzymatic esterification to produce1,3-DAG. Compared with stirred tank reactor, the load ofIM-LU was reduced and the reaction was accelerated. After45min reaction, the esterificationefficiency was86.4%and the1,3-DAG content was58.3wt%. The BCR can avoid the shearinactivation of immobilized enzyme due to mechanical agitation. The stability of the enzymewas improved.
5. DAG-enriched oil was prepared by molecular distillation. Its melting andcrystallization properties, solid fat content and fatty acid composition were investigated. TheDAG oil was used to substitute hydrogenated vegetable oil BL-39in whipped cream. Theresult showed that with the DAG substitution increasing, the average particle size, surfaceprotein concentration, partial coalescence of fat and textural property values of whippedcream increased. DAG substitution of5%–15%could shorten the whipping time and improvethe standing stability. And the organoleptic property had not changed much as compared withthe control. Sample with20%DAG substitution exhibited weak standing stability andorganoleptic property. As a result, it was inappropriate to be applied in whipped cream in thepresent study.
引文
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