Modulating enzyme activity using ionic liquids or surfactants

Applied Microbiology and Biotechnology

Volumn 98, Issue 2, 2014, Pages 545-554

  Goldfeder, Mor ^a   Fishman, Ayelet ^a  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

Enzyme activation; Ionic liquids; Mixed micelles; Surfactants

Indexed keywords

ENZYME ACTIVATORS; ENZYMES; IONIC LIQUIDS; PROTEIN CONFORMATION; SOLUBILITY; SOLVENTS; SURFACE-ACTIVE AGENTS;

EID: 84894488335     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-013-5395-7     Document Type: Review

References (80)

1. Ajloo D, Sangian M, Ghadamgahi M, Evini M, Saboury AA (2013) Effect of two imidazolium derivatives of ionic liquids on the structure and activity of adenosine deaminase. Int J Biol Macromol 55:47-61
2. Alfani F, Cantarella M, Spreti N, Germani R, Savelli G (2000) α-Chymotrypsin superactivity in cetyltrialkylammonium bromide-rich media. Appl Biochem Biotechnol 88(1-3):1-15
3. Baird S, Kelly SM, Price NC, Jaenicke E, Meesters C, Nillius D, Decker H, Nairn J (2007) Hemocyanin conformational changes associated with SDS-induced phenol oxidase activation. Biochim Biophys Acta, Proteins Proteomics 1774(11):1380-1394 (Pubitemid 350123200)
4. Biasutti MA, Abuin EB, Silber JJ, Correa NM, Lissi EA (2008) Kinetics of reactions catalyzed by enzymes in solutions of surfactants. Adv Colloid Interface Sci 136(1-2):1-24 (Pubitemid 350245642)
5. Bommarius AS, Blum JK, Abrahamson MJ (2011) Status of protein engineering for biocatalysts: how to design an industrially useful biocatalyst. Curr Opin Chem Biol 15(2):194-200
6. Brzozowski AM, Savage H, Verma CS, Turkenburg JP, Lawson DM, Svendsen A, Patkar S (2000) Structural origins of the interfacial activation in Thermomyces (Humicola) lanuginosa lipase. Biochemistry (Mosc) 39(49):15071-15082
7. Carvalho CML, Cabral JMS (2000) Reverse micelles as reaction media for lipases. Biochimie 82(11):1063-1085
8. Celej MS, D'Andrea MG, Campana PT, Fidelio GD, Bianconi ML (2004) Superactivity and conformational changes on alpha-chymotrypsin upon interfacial binding to cationic micelles. Biochem J 378(3):1059-1066 (Pubitemid 38406886)
9. Chen S-X, Wei D-Z, Hu Z-H (2001) Synthesis of galacto-oligosaccharides in AOT/isooctane reverse micelles by β-galactosidase. J Mol Catal B Enzym 16(2):109-114 (Pubitemid 33016365)
10. Chiappe C, Neri L, Pieraccini D (2006) Application of hydrophilic ionic liquids as co-solvents in chloroperoxidase catalyzed oxidations. Tetrahedron Lett 47(29):5089-5093 (Pubitemid 43867618)
11. Cong Y, Zhang Q, Woolford D, Schweikardt T, Khant H, Dougherty M, Ludtke SJ, Chiu W, Decker H (2009) Structural mechanism of SDS-induced enzyme activity of scorpion hemocyanin revealed by electron cryomicroscopy. Structure 17(5):749-758
12. da Costa Lopes AM, João KG, Bogel-Łukasik E, Roseiro LB, Bogel-Łukasik R (2013) Pretreatment and fractionation of wheat straw using various ionic liquids. J Agric Food Chem 61(33):7874-7882
13. Das D, Das D, Das PK (2008) Improved activity of enzymes in mixed cationic reverse micelles with imidazolium-based surfactants. Biochimie 90(5):820-829
14. Decker H, Rimke T (1998) Tarantula hemocyanin shows phenoloxidase activity. J Biol Chem 273(40):25889-25892 (Pubitemid 28475819)
15. Delorme V, Dhouib R, Canaan S, Fotiadu F, Carrière F, Cavalier J-F (2011) Effects of surfactants on lipase structure, activity, and inhibition. Pharm Res 28(8):1831-1842
16. Diop A, Bouanzza AH, Daneault C, Montplaisir D (2013) New ionic liquids for the dissolution of lignin. BioResources 8(3):4270-4282
17. Domingez de Maria P (2011) Ionic liquids in biotransformations and organocatalysis: solvents and beyond. Wiley & Sons, Hoboken, NJ
18. Domínguez de María P, Maugeri Z (2011) Ionic liquids in biotransformations: from proof-of-concept to emerging deep-eutectic-solvents. Curr Opin Chem Biol 15(2):220-225
19. Durand E, Lecomte J, Villeneuve P (2013) Deep eutectic solvents: synthesis, application, and focus on lipase-catalyzed reactions. Eur J Lipid Sci Technol 115(4):379-385
20. Espín JC, Wichers HJ (1999) Activation of a latent mushroom (Agaricus bisporus) tyrosinase isoform by sodium dodecyl sulfate (SDS). Kinetic properties of the SDS-activated isoform J Agric Food Chem 47(9):3518-3525 (Pubitemid 29449462)
21. Fan Y, Zhang S, Wang Q, Li J, Fan H, Shan D (2013) Interaction of an amino-functionalized ionic liquid with enzymes: a fluorescence spectroscopy study. Spectrochim Acta, Pt A: Mol Biomol Spectrosc 105:297-303
22. Fernandez-Lorente G, Palomo JM, Cabrera Z, Fernandez-Lafuente R, Guisán JM (2007) Improved catalytic properties of immobilized lipases by the presence of very low concentrations of detergents in the reaction medium. Biotechnol Bioeng 97(2):242-250 (Pubitemid 46852921)
23. Gandia-Herrero F, Jimenez-Atienzar M, Cabanes J, Garcia-Carmona F, Escribano J (2005) Differential activation of a latent polyphenol oxidase mediated by sodium dodecyl sulfate. J Agric Food Chem 53(17):6825-6830 (Pubitemid 41260730)
24. Goldfeder M, Egozy M, Shuster Ben-Yosef V, Adir N, Fishman A (2013) Changes in tyrosinase specificity by ionic liquids and sodium dodecyl sulfate. Appl Microbiol Biotechnol 97(5):1953-1961
25. Gorke JT, Srienc F, Kazlauskas RJ (2008) Hydrolase-catalyzed biotransformations in deep eutectic solvents. Chem Commun(10):1235-1237 (Pubitemid 351328030)
26. Gorke J, Srienc F, Kazlauskas R (2010) Toward advanced ionic liquids. Polar, enzyme-friendly solvents for biocatalysis. Biotechnol Bioproc E 15(1):40-53
27. Greaves TL, Drummond CJ (2008) Ionic liquids as amphiphile self-assembly media. Chem Soc Rev 37(8):1709-1726
28. Heintz A, Lehmann JK, Kozlova SA, Balantseva EV, Bazyleva AB, Ondo D (2010) Micelle formation of alkylimidazolium ionic liquids in water and in ethylammonium nitrate ionic liquid: a calorimetric study. Fluid Phase Equilib 294(1-2):187-196
29. Hermoso J, Pignol D, Kerfelec B, Crenon I, Chapus C, Fontecilla-Camps JC (1996) Lipase activation by nonionic detergents: the crystal structure of the porcine lipase-colipase-tetraethylene glycol monooctyl ether complex. J Biol Chem 271(30):18007-18016 (Pubitemid 26250786)
30. Hinckley G, Mozhaev V, Budde C, Khmelnitsky Y (2002) Oxidative enzymes possess catalytic activity in systems with ionic liquids. Biotechnol Lett 24(24):2083-2087 (Pubitemid 36093402)
31. Husum T, Jorgensen C, Christensen M, Kirk O (2001) Enzyme catalysed synthesis in ambient temperature ionic liquids. Biocatal Biotransform 19(4):331-338 (Pubitemid 33121151)
32. Itoh T, Han S, Matsushita Y, Hayase S (2004) Enhanced enantioselectivity and remarkable acceleration on the lipase-catalyzed transesterification using novel ionic liquids. Green Chem 6(9):437-439 (Pubitemid 39472340)
33. Jaeger VW, Pfaendtner J (2013) Structure, dynamics, and activity ofxylanase solvated in binary mixtures of ionic liquid and water. ACS Chem Biol 8(6):1179-1186
34. Jones MN, Finn A, Mosavi-Movahedi A, Waller BJ (1987) The activation of Aspergillus niger catalase by sodium n-dodecyl-sulphate. Biochim Biophys Acta Protein Struct M 913(3):395-398
35. Judge RA, Takahashi S, Longenecker KL, Fry EH, Abad-Zapatero C, Chiu ML (2009) The effect of ionic liquids on protein crystallization and x-ray diffraction resolution. Cryst Growth Des 9(8):3463-3469
36. Jungnickel C, Łuczak J, Ranke J, Fernández JF, Müller A, Thöming J (2008) Micelle formation of imidazolium ionic liquids in aqueous solution. Colloids Surf Physicochem Eng Aspects 316(1-3):278-284 (Pubitemid 351173730)
37. Jutz F, Andanson J-M, Baiker A (2010) Ionic liquids and dense carbon dioxide: a beneficial biphasic system for catalysis. Chem Rev 111(2):322-353
38. Kaftzik N, Wasserscheid P, Kragl U (2002) Use of ionic liquids to increase the yield and enzyme stability in the β-galactosidase catalysed synthesis of N-acetyllactosamine. Org Process Res Dev 6(4):553-557
39. Kazlauskas RJ, Bornscheuer UT (2009) Finding better protein engineering strategies. Nat Chem Biol 5(8):526-529
40. Kim K-W, Song B, Choi M-Y, Kim M-J (2001) Biocatalysis in ionic liquids: markedly enhanced enantioselectivity of lipase. Org Lett 3(10):1507-1509 (Pubitemid 33631621)
41. Lai J-Q, Li Z, Lu Y-H, Yang Z (2011) Specific ion effects of ionic liquids on enzyme activity and stability. Green Chem 13(7):1860-1868
42. Lang M, Kamrat T, Nidetzky B (2006) Influence of ionic liquid cosolvent on transgalactosylation reactions catalyzed by thermostable β- glycosylhydrolase CelB from Pyrococcus furiosus. Biotechnol Bioeng 95(6):1093-1100 (Pubitemid 44901324)
43. Lee JK, Kim M-J (2002) Ionic liquid-coated enzyme for biocatalysis in organic solvent. J Org Chem 67(19):6845-6847
44. Lichtenecker R, Schmid W (2009) Application of various ionic liquids as cosolvents for chloroperoxidase-catalysed biotransformations. Monatsh Chem 140(5):509-512
45. Lindberg D, de la Fuente Revenga M, Widersten M (2010) Deep eutectic solvents (DESs) are viable cosolvents for enzyme-catalyzed epoxide hydrolysis. J Biotechnol 147(3-4):169-171
46. López-serrano D, Sanchez-Amat A, Solano F (2002) Cloning and molecular characterization of a SDS-activated tyrosinase from Marinomonas mediterranea. Pigment Cell Res 15(2):104-111 (Pubitemid 34536323)
47. Lou W-Y, Zong M, Wu H (2005) Enzymic asymmetric hydrolysis of d, l-p-hydroxyphenylglycine methyl ester in aqueous ionic liquid co-solvent mixtures. Biotechnol Appl Biochem 41(2):151-156 (Pubitemid 40523411)
48. Lou W-Y, Zong M-H, Liu Y-Y, Wang J-F (2006) Efficient enantioselective hydrolysis of d, l-phenylglycine methyl ester catalyzed by immobilized Candida antarctica lipase B in ionic liquid containing systems. J Biotechnol 125(1):64-74 (Pubitemid 44066601)
49. Magalhaes da Silva SP, da Costa Lopes AM, Roseiro LB, Bogel-Lukasik R (2013) Novel pre-treatment and fractionation method for lignocellulosic biomass using ionic liquids. RSC Adv 3(36):16040-16050
50. Martinek K, Levashov AV, Klyachko N, Khmelnitski YL, Berezin IV (1986) Micellar enzymology. Eur J Biochem 155(3):453-468
51. Mehta SK, Kaur K (2010) Ionic liquid microemulsions and their technological applications Indian J Chem. Sect A 49:662-684
52. Mogensen JE, Sehgal P, Otzen DE (2005) Activation, inhibition, and destabilization of Thermomyces lanuginosus lipase by detergents. Biochemistry (Mosc) 44(5):1719-1730 (Pubitemid 40204413)
53. Moniruzzaman M, Kamiya N, Goto M (2008a) Biocatalysis in water-in-ionic liquid microemulsions: a case study with horseradish peroxidase. Langmuir 25(2):977-982
54. Moniruzzaman M, Kamiya N, Nakashima K, Goto M (2008b) Water-in-ionic liquid microemulsions as a new medium for enzymatic reactions. Green Chem 10(5):497-500 (Pubitemid 351624322)
55. Moniruzzaman M, Nakashima K, Kamiya N, Goto M (2010) Recent advances of enzymatic reactions in ionic liquids. Biochem Eng J 48(3):295-314
56. Mutschler J, Rausis T, Bourgeois J-M, Bastian C, Zufferey D, Mohrenz IV, Fischer F (2009) Ionic liquid-coated immobilized lipase for the synthesis of methylglucose fatty acid esters. Green Chem 11(11):1793-1800
57. Naushad M, Alothman ZA, Khan AB, Ali M (2012) Effect of ionic liquid on activity, stability, and structure of enzymes: a review. Int J Biol Macromol 51(4):555-560
58. Nillius D, Jaenicke E, Decker H (2008) Switch between tyrosinase and catecholoxidase activity of scorpion hemocyanin by allosteric effectors. FEBS Lett 582(5):749-754
59. Nordwald EM, Kaar JL (2013) Mediating electrostatic binding of 1-butyl-3-methylimidazolium chloride to enzyme surfaces improves conformational stability. J Phys Chem B 117(30):8977-8986
60. Okochi M, Nakagawa I, Kobayashi T, Hayashi S, Furusaki S, Honda H (2007) Enhanced activity of 3α-hydroxysteroid dehydrogenase by addition of the co-solvent 1-butyl-3-methylimidazolium (l)-lactate in aqueous phase of biphasic systems for reductive production of steroids. J Biotechnol 128(2):376-382 (Pubitemid 46074192)
61. Otzen D (2011) Protein-surfactant interactions: a tale of many states. Biochim Biophys Acta, Proteins Proteomics 1814(5):562-591
62. Pavlidis IV, Gournis D, Papadopoulos GK, Stamatis H (2009) Lipases in water-in-ionic liquid microemulsions: structural and activity studies. J Mol Catal B Enzym 60(1-2):50-56
63. Pinto PCAG, Costa SPF, Lima JLFC, Saraiva MLMFS (2012) β-Galactosidase activity in mixed micelles of imidazolium ionic liquids and sodium dodecylsulfate: a sequential injection kinetic study. Talanta 96:26-33
64. Qiu Z, Texter J (2008) Ionic liquids in microemulsions. Curr Opin Colloid Interface Sci 13(4):252-262 (Pubitemid 351814830)
65. Rehmann L, Ivanova E, Ferguson JL, Gunaratne HQN, Seddon KR, Stephens GM (2012) Measuring the effect of ionic liquids on laccase activity using a simple, parallel method. Green Chem 14(3):725-733
66. Saeidian S, Keyhani E, Keyhani J (2007) Effect of ionic detergents, nonionic detergents, and chaotropic agents on polyphenol oxidase activity from dormant saffron (Crocus sativus L.) corms. J Agric Food Chem 55(9):3713-3719 (Pubitemid 46806597)
67. Savelli G, Spreti N, Di Profio P (2000) Enzyme activity and stability control by amphiphilic self-organizing systems in aqueous solutions. Curr Opin Colloid Interface Sci 5(1-2):111-117
68. Shin H-J, Yang J-W (1994) Galacto-oligosaccharide production by β-galactosidase in hydrophobic organic media. Biotechnol Lett 16(11):1157-1162 (Pubitemid 24368262)
69. Shipovskov S, Gunaratne HQN, Seddon KR, Stephens G (2008) Catalytic activity of laccases in aqueous solutions of ionic liquids. Green Chem 10(7):806-810 (Pubitemid 351905027)
70. Spreti N, Di Profio P, Marte L, Bufali S, Brinchi L, Savelli G (2001) Activation and stabilization of α-chymotrypsin by cationic additives. Eur J Biochem 268(24):6491-6497 (Pubitemid 34014757)
71. Tavares APM, Pereira JAN, Xavier AMRB (2012) Effect of ionic liquids activation on laccase from Trametes versicolor: enzymatic stability and activity. Eng Life Sci 12(6):648-655
72. van Rantwijk F, Sheldon RA (2007) Biocatalysis in ionic liquids. Chem Rev 107(6):2757-2785 (Pubitemid 47033772)
73. Verma SK, Ghosh KK (2011) Effect of cationic surfactants on the enzymatic activity of α-chymotrypsin. Kinet Catal 52(1):6-10
74. Wehofsky N, Wespe C, Cerovsky V, Pech A, Hoess E, Rudolph R, Bordusa F (2008) Ionic liquids and proteases: a clean alliance for semisynthesis. ChemBioChem 9(9):1493-1499
75. Xue L, Li Y, Zou F, Lu L, Zhao Y, Huang X, Qu Y (2012) The catalytic efficiency of lipase in a novel water-in-[Bmim][PF6] microemulsion stabilized by both AOT and Triton X-100. Colloids Surf B: Biointerfaces 92:360-366
76. Yang Z (2009) Hofmeister effects: an explanation for the impact of ionic liquids on biocatalysis. J Biotechnol 144(1):12-22
77. Yoshiyama K, Abe Y, Hayase S, Nokami T, Itoh T (2013) Synergetic activation of lipase by an amino acid with alkyl-PEG sulfate ionic liquid. Chem Lett 42(6):663-665
78. Zhao H (2010) Methods for stabilizing and activating enzymes in ionic liquids - a review. J Chem Technol Biotechnol 85(7):891-907
79. Zhao H, Baker GA, Holmes S (2011) Protease activation in glycerol-based deep eutectic solvents. J Mol Catal B Enzym 72(3-4):163-167
80. Zheng L, Zhang S, Yu X, Zhao L, Gao G, Yang X, Duan H, Cao S (2006) Enhancement of enantioselectivity in lipase-catalyzed resolution of N-(2-ethyl-6-methylphenyl)alanine by additives. J Mol Catal B Enzym 38(1):17-23 (Pubitemid 43028550)