有机溶剂中的酶催化过程。
Enzyme-catalyzed processes in organic solvents.
作者信息
Zaks A, Klibanov A M
出版信息
Proc Natl Acad Sci U S A. 1985 May;82(10):3192-6. doi: 10.1073/pnas.82.10.3192.
Abstract
Three different lipases (porcine pancreatic, yeast, and mold) can vigorously act as catalysts in a number of nearly anhydrous organic solvents. Various transesterification reactions catalyzed by porcine pancreatic lipase in hexane obey Michaelis-Menten kinetics. The dependence of the catalytic activity of the enzyme in organic media on the pH of the aqueous solution from which it was recovered is bell-shaped, with the maximum coinciding with the pH optimum of the enzymatic activity in water. The catalytic power exhibited by the lipases in organic solvents is comparable to that displayed in water. In addition to transesterification, lipases can catalyze several other processes in organic media including esterification, aminolysis, acyl exchange, thiotransesterification, and oximolysis; some of these reactions proceed to an appreciable extent only in nonaqueous solvents.
摘要
三种不同的脂肪酶（猪胰脂肪酶、酵母脂肪酶和霉菌脂肪酶）能在多种几乎无水的有机溶剂中有力地充当催化剂。猪胰脂肪酶在己烷中催化的各种酯交换反应遵循米氏动力学。该酶在有机介质中的催化活性对其回收所用水溶液pH的依赖性呈钟形，最大值与该酶在水中的活性最适pH一致。脂肪酶在有机溶剂中展现出的催化能力与在水中相当。除酯交换反应外，脂肪酶还能在有机介质中催化其他几种反应，包括酯化、氨解、酰基交换、硫代酯交换和肟解反应；其中一些反应仅在非水溶剂中能进行到可观的程度。
相似文献
1
Enzyme-catalyzed processes in organic solvents.有机溶剂中的酶催化过程。
Proc Natl Acad Sci U S A. 1985 May;82(10):3192-6. doi: 10.1073/pnas.82.10.3192.
2
Lipase-catalyzed reactions in organic media: competition and applications.有机介质中脂肪酶催化的反应：竞争与应用
Biochim Biophys Acta. 1987 Jan 5;911(1):117-20. doi: 10.1016/0167-4838(87)90278-0.
3
Hydration-aggregation pretreatment for drastically improving esterification activity of commercial lipases in non-aqueous media.水合-聚集预处理可显著提高商业脂肪酶在非水介质中的酯化活性。
Enzyme Microb Technol. 2017 Oct;105:30-37. doi: 10.1016/j.enzmictec.2017.06.007. Epub 2017 Jun 12.
4
Lipase-catalyzed transesterification in organic media: solvent effects on equilibrium and individual rate constants.有机介质中脂肪酶催化的酯交换反应：溶剂对平衡和各速率常数的影响。
Biotechnol Bioeng. 1998 Sep 20;59(6):684-94.
5
Enzymatic catalysis in organic media at 100 degrees C.100摄氏度下有机介质中的酶催化作用。
Science. 1984 Jun 15;224(4654):1249-51. doi: 10.1126/science.6729453.
6
A lipid-coated lipase as an efficient hydrolytic catalyst in the two-phase aqueous-organic system.一种脂质包被的脂肪酶作为双相水-有机体系中的高效水解催化剂。
Biotechnol Bioeng. 2001 Sep;76(2):157-63. doi: 10.1002/bit.1155.
7
Applications of immobilized lipases to transesterification and esterification reactions in nonaqueous systems.固定化脂肪酶在非水体系中酯交换反应和酯化反应中的应用。
Enzyme Microb Technol. 1993 Feb;15(2):133-9. doi: 10.1016/0141-0229(93)90037-3.
8
Factors affecting the resolution of dl-menthol by immobilized lipase-catalyzed esterification in organic solvent.有机溶剂中固定化脂肪酶催化酯化拆分dl-薄荷醇的影响因素
J Agric Food Chem. 2002 Jan 16;50(2):262-5. doi: 10.1021/jf010657j.
9
Solvent effects in lipase-catalysed transesterification reactions.脂肪酶催化酯交换反应中的溶剂效应
Acta Chem Scand (Cph). 1990 Nov;44(10):1032-5. doi: 10.3891/acta.chem.scand.44-1032.
10
Optimizing the salt-induced activation of enzymes in organic solvents: effects of lyophilization time and water content.优化盐诱导的酶在有机溶剂中的活化：冻干时间和含水量的影响
Biotechnol Bioeng. 1999 Apr 20;63(2):233-41. doi: 10.1002/(sici)1097-0290(19990420)63:2<233::aid-bit12>3.0.co;2-s.
引用本文的文献
1
Development of DNase-1 Loaded Polymeric Nanoparticles Synthesized by Inverse Flash Nanoprecipitation for Neutrophil-Mediated Drug Delivery to In Vitro Thrombi.通过反向闪蒸纳米沉淀法合成的载有脱氧核糖核酸酶-1的聚合物纳米颗粒用于中性粒细胞介导的药物体外血栓递送的研究进展。
Adv Healthc Mater. 2025 Jun;14(15):e2404584. doi: 10.1002/adhm.202404584. Epub 2025 May 8.
2
Toward Design Principles for Biomolecular Condensates for Metabolic Pathways.代谢途径生物分子凝聚物的设计原则
Adv Biol (Weinh). 2025 May;9(5):e2400672. doi: 10.1002/adbi.202400672. Epub 2025 Apr 7.
3
Active Site Studies to Explain Kinetics of Lipases in Organic Solvents Using Molecular Dynamics Simulations.利用分子动力学模拟进行活性位点研究以解释脂肪酶在有机溶剂中的动力学
J Phys Chem B. 2025 Jan 9;129(1):475-486. doi: 10.1021/acs.jpcb.4c05738. Epub 2024 Dec 29.
4
Latest Trends in Lipase-Catalyzed Synthesis of Ester Carbohydrate Surfactants: From Key Parameters to Opportunities and Future Development.脂肪酶催化合成酯型糖基表面活性剂的最新趋势：从关键参数到机遇和未来发展。
Int J Mol Sci. 2024 Mar 27;25(7):3727. doi: 10.3390/ijms25073727.
5
lipase B performance in organic solvent at varying water activities studied by molecular dynamics simulations.通过分子动力学模拟研究脂肪酶B在不同水分活度的有机溶剂中的性能。
Comput Struct Biotechnol J. 2023 Oct 31;21:5451-5462. doi: 10.1016/j.csbj.2023.10.049. eCollection 2023.
6
Yeast Lipid Produced through Glycerol Conversions and Its Use for Enzymatic Synthesis of Amino Acid-Based Biosurfactants.酵母油脂的甘油转化生产及其在氨基酸型生物表面活性剂酶法合成中的应用。
Int J Mol Sci. 2022 Dec 31;24(1):714. doi: 10.3390/ijms24010714.
7
Peptide conformational imprints enhanced the catalytic activity of papain for esterification.肽构象印记增强了木瓜蛋白酶的酯化催化活性。
Front Bioeng Biotechnol. 2022 Aug 16;10:943751. doi: 10.3389/fbioe.2022.943751. eCollection 2022.
8
Characterization of immobilized tyrosinase - an enzyme that is stable in organic solvent at 100 °C.固定化酪氨酸酶的特性——一种在100℃的有机溶剂中稳定的酶。
RSC Adv. 2018 Nov 27;8(69):39529-39535. doi: 10.1039/c8ra07559j. eCollection 2018 Nov 23.
9
Enzymatic Cascade for the Synthesis of 2,5-Furandicarboxylic Acid in Biphasic and Microaqueous Conditions: 'Media-Agnostic' Biocatalysts for Biorefineries.两相和微水相条件下用于 2,5-呋喃二甲酸合成的酶级联反应：生物精炼厂的“介质不敏感”生物催化剂。
ChemSusChem. 2022 May 6;15(9):e202102704. doi: 10.1002/cssc.202102704. Epub 2022 Apr 19.
10
Stereoselective Promiscuous Reactions Catalyzed by Lipases.脂肪酶催化的立体选择性杂反应。
Int J Mol Sci. 2022 Feb 28;23(5):2675. doi: 10.3390/ijms23052675.
本文引用的文献
1
Immobilized enzymes and cells as practical catalysts.固定化酶和细胞作为实用催化剂。
Science. 1983 Feb 11;219(4585):722-7. doi: 10.1126/science.219.4585.722.
2
Some factors in the interpretation of protein denaturation.蛋白质变性解读中的一些因素。
Adv Protein Chem. 1959;14:1-63. doi: 10.1016/s0065-3233(08)60608-7.
3
A chemical modification to make horseradish peroxidase soluble and active in benzene.一种使辣根过氧化物酶在苯中可溶且具有活性的化学修饰。
Biochem Biophys Res Commun. 1984 May 31;121(1):261-5. doi: 10.1016/0006-291x(84)90716-2.
4
Enzymatic catalysis in organic media at 100 degrees C.100摄氏度下有机介质中的酶催化作用。
Science. 1984 Jun 15;224(4654):1249-51. doi: 10.1126/science.6729453.
5
Ester synthesis catalyzed by polyethylene glycol-modified lipase in benzene.聚乙二醇修饰的脂肪酶在苯中催化酯合成反应。
Biochem Biophys Res Commun. 1984 Jul 31;122(2):845-50. doi: 10.1016/s0006-291x(84)80111-4.
6
Reactivity of active sites of chymotrypsin suspended in an organic medium.悬浮于有机介质中的胰凝乳蛋白酶活性位点的反应性。
Arch Biochem Biophys. 1966 Jul;115(1):44-7. doi: 10.1016/s0003-9861(66)81035-4.
7
Action of organophosphates on pancreatic lipase.有机磷酸酯对胰腺脂肪酶的作用。
Biochim Biophys Acta. 1969 Mar 18;178(1):196-8. doi: 10.1016/0005-2744(69)90151-x.
Zotero 插件