Effects of methanol on lipases: Molecular, kinetic and process issues in the production of biodiesel

Biotechnology Journal

Volumn 10, Issue 1, 2015, Pages 22-30

  Lotti, Marina ^a   Pleiss, Jürgen ^b   Valero, Francisco ^c   Ferrer, Pau ^c  

^a UNIVERSITY OF MILANO BICOCCA   (Italy)

^b UNIVERSITY OF STUTTGART   (Germany)

^c UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

Biodiesel; Inactivation; Lipase; Methanol

Indexed keywords

BIODIESEL; ENZYMES; FATTY ACIDS; METHANOL; ORGANIC SOLVENTS;

BIOCATALYTIC PROCESS; BIODIESEL PRODUCTION; BIOTECHNOLOGICAL PRODUCTION; DIFFERENT MECHANISMS; INACTIVATION; INDUSTRIAL PROCESSS; SHORT CHAIN ALCOHOLS; SUBSTRATE INHIBITION;

LIPASES;

ALCOHOL DERIVATIVE; BIODIESEL; METHANOL; TRIACYLGLYCEROL LIPASE; WATER; BIOFUEL;

BIOFUEL PRODUCTION; CATALYSIS; ENZYME ENGINEERING; ENZYME INACTIVATION; ENZYME INHIBITION; ENZYME SYNTHESIS; KINETICS; MOLECULAR DYNAMICS; MUTAGENESIS; PRIORITY JOURNAL; PROTEIN UNFOLDING; REVIEW; SOLVENT EFFECT; THERMODYNAMICS; BIOTECHNOLOGY; CHEMISTRY; ENZYME STABILITY; METABOLISM; PHYSIOLOGY;

BIOFUELS; BIOTECHNOLOGY; ENZYME STABILITY; LIPASE; METHANOL;

EID: 84921604273     PISSN: 18606768     EISSN: 18607314     Source Type: Journal    
DOI: 10.1002/biot.201400158     Document Type: Review

References (86)

1. Parawira, W., Biotechnological production of biodiesel fuel using biocatalysed transesterification: A review. Crit. Rev. Biotechnol. 2009, 29, 82-93.
2. Fjerbaek, L., Christensen, K. V., Norddahl, B., A review of the current state of biodiesel production using enzymatic transesterification. Biotechnol. Bioeng. 2009, 102, 1298-1315.
3. Adamczak, M., Bornscheuer, U. Y., Bednarski, W., The application of biotechnological methods for the synthesis of biodiesel. Eur. J. Lipid Sci. Technol. 2009, 111, 808-813.
4. Tan, T., Lu, J., Nie, K., Deng, L., Wang, F., Biodiesel production with immobilized lipase: A review. Biotechnol. Adv. 2010, 28, 628-634.
5. Christopher, L. P., Kumar, H., Zambare, V.P., Enzymatic biodiesel: Challenges and opportunities. Appl. Energy 2014, 119, 497-520.
6. Deng, L., Xu, X., Haraldsson, G. G., Tan, T., Wang, F., Enzymatic Production of Alkyl Esters Through Alcoholysis: A Critical Evaluation of Lipases and Alcohols. J. Am. Oil Chem. Soc. 2005, 82, 341-347.
7. Uphues, G., Saint Victor, M.-E., Raths, H.-C., Biermann, M. et al., Industrial surfactant syntheses, in: Texter J (Ed.), Reactions and synthesis in surfactant systems, CRC Press, 2001.
8. Ozyilmaz, G., Gezer, E., Production of aroma esteres by immobilized Candida rugosa and porcine pancreatic lipase into calcium alginate gel. J. Mol. Catal. B-Enzym. 2010, 64, 140-145.
9. Luo, Y., Zheng, Y., Jiang, Z., Ma, Y., Wei, D., A novel psychrophilic lipase from Pseudomonas fluorescens with unique property in chiral resolution and biodiesel production via transesterification. Appl. Microbiol. Biotechnol. 2006, 73, 349-355.
10. Yang, K. S., Sohn, J. H., Kim, H.K., Catalytic properties of a lipase from Photobacterium lipolyticum for biodiesel production containing a high methanol concentration. J. Biosci. Bioeng. 2009, 107, 599-604.
11. Zhang, H., Zhang, F., Li, Z., Gene analysis, optimized production and property of marine lipase from Bacillus pumilus B106 associated with South China Sea Halichondria rugosa World. J. Microbiol. Biotechnol. 2009, 25, 1267-1274.
12. Korman, T. P., Sahachartsiri, B., Charbonneau, D. M., Huang, G. L. et al., Dieselzymes: development of a stable and methanol tolerant lipase for biodiesel production by directed evolution. Biotechnol. Biofuels 2013, 6, 70.
13. Dror, A., Shemesh, E., Dayan, N., Fishman, A., Protein engineering by random mutagenesis and structure-guided consensus of Geobacillus stearothermophilus Lipase T6 for enhanced stability in methanol. Appl. Environ. Microbiol. 2014, 80, 1515-1527.
14. Park, H. J., Joo, J. C., Park, K., Kim, Y. H., Yoo, Y. J., Stabilisation of Candida antarctica lipase B in hydrophylic organic solvent by rational design of hydrogen bond. Biotechnol. Bioprocess Eng. 2012, 17, 722-728.
15. Martinelle, M., Hult, K., Kinetics of acyl transfer reactions in organic media catalysed by Candida antarctica lipase B. Biochim. Biophys. Acta 1995, 1251, 191-197.
16. Bousquet-Dubouch, M.-P., Graber, M., Sousa, N., Lamare, S., Legoy, M.D., Alcoholysis catalyzed by Candida antarctica lipase B in a gas/solid system obeys a Ping Pong Bi Bi mechanism with competitive inhibition by the alcohol substrate and water. Biochim. Biophys. Acta 2011, 550, 90-99.
17. Chulalaksananukul, W., Condoret, J. S., Delorme, P., Willemot, R. M., Kinetic study of esterification by immobilized lipase in n-hexane. FEBS Lett. 1990, 276, 181-184.
18. Samukawa, T., Kaieda, M., Matsumoto, T., Ban, K. et al., Pretreatment of immobilized Candida antarctica lipase for biodiesel fuel production from plant oil. J. Biosci. Bioeng. 2000, 90, 180-183.
19. Kaieda, M., Samukawa, T., Kondo, A., Fukuda, H., Effect of methanol and water contents on production of biodiesel fuel from plant oil catalyzed by various lipases in a solvent-free system. J. Biosci. Bioeng. 2001, 91, 12-15.
20. Tan, T., Nie, K., Wang, F., Production of biodiesel by immobilized Candida sp. lipase at high water content. Appl. Biochem. Biotechnol. 2006, 128, 109-116.
21. Robles-Medina, A., Gonzalez-Moreno, P.A., Esteban-Cerdan, L., Molina-Grima, E., Biocatalysis: towards ever greener biodiesel production. Biotechnol. Adv. 2009, 27, 398-408.
22. Santambrogio, C., Sasso, F., Natalello, A., Brocca, S. et al., Effects of methanol on a methanol-tolerant bacterial lipase. Appl. Microbiol. Biotechnol. 2013, 97, 8609-8618.
23. Natalello, A., Sasso, F., Secundo, F., Enzymatic transesterification monitored by an easy-to-use Fourier transform infrared spectroscopy method. Biotechnol. J. 2013, 8, 133-138.
24. Shimada, Y., Watanabe, Y., Samukawa, T., Sugihara, A. et al., Conversion of vegetable oil to biodiesel using immobilized Candida Antarctica lipase. J. Am. Oil Chem. Soc. 1999, 76, 789-793.
25. Anderson, E. M., Larsson, K. M., Kirk, O., One biocatalyst-many applications: the use of Candida antarctica B lipase in organic synthesis Biocatal. Biotransf. 1998, 16, 181-204.
26. Sym, E. A., Action of esterase in the presence of organic solvents. Biochem. J. 1936, 30, 609-617.
27. Laane, C., Boeren, S., Vos, K., Veeger, C., Rules for optimization of biocatalysis in organic solvents. Biotechnol. Bioeng. 1987, 30, 81-87.
28. van Erp, S. H., Kamenskaya, E.O., Khmelnitsky, Y. L., The effect of water content and nature of organic solvent on enzyme activity in low-water media. A quantitative description. Eur. J. Biochem. 1991, 202, 379-384.
29. Dimoula, K., Pohl, M., Buchs, J., Spiess, A. C., Substrate and water adsorption phenomena in a gas/solid enzymatic reactor. Biotechnol. J. 2009, 4, 712-721.
30. Branco, R. J., Graber, M., Denis, V., Pleiss, J., Molecular mechanism of the hydration of Candida antarctica lipase B in the gas phase: Water adsorption isotherms and molecular dynamics simulations. Chembiochem. 2009, 10, 2913-2919.
31. Deshpande, A., Nimsadkar, S., Mande, S. C., Effect of alcohols on protein hydration: crystallographic analysis of hen egg-white lysozyme in the presence of alcohols. Acta Crystallogr. D. Biol. Crystallogr. 2005, 61, 1005-1008.
32. Mattos, C., Bellamacina, C. R., Peisach, E., Pereira, A. et al., Multiple solvent crystal structures: probing binding sites, plasticity and hydration. J. Mol. Biol. 2006, 357, 1471-1482.
33. Smith, R. R., Canady, W. J., Solvation effects upon the thermodynamic substrate activity; correlation with the kinetics of enzyme catalyzed reactions. I. Effects of added reagents such as methanol upon alpha-chymotrypsin. Biophys. Chem. 1992, 43, 173-187.
34. van Tol, J. B., Stevens, R. M., Veldhuizen, W. J., Jongejan, J. A., Duine, J. A., Do organic solvents affect the catalytic properties of lipase? Intrinsic kinetic parameters of lipases in ester hydrolysis and formation in various organic solvents. Biotechnol. Bioeng. 1995, 47, 71-81.
35. van Tol, J. B., Jongejan, J. A., Duine, J. A., Kierkels, H. G. et al., Thermodynamic and kinetic parameters of lipase-catalyzed ester hydrolysis in biphasic systems with varying organic solvents. Biotechnol Bioeng 1995, 48, 179-189.
36. Sandoval, G., Condoret, J. S., Monsan, P., Marty, A., Esterification by immobilized lipase in solvent-free media: kinetic and thermodynamic arguments. Biotechnol. Bioeng. 2002, 78, 313-320.
37. Lee, S. B., Enzyme reaction kinetics in organic solvents: A theoretical kinetic model and comparison with experimental observations. J. Ferment. Bioeng. 1995, 79, 479-484.
38. Kulschewski, T., Sasso, F., Secundo, F., Lotti, M., Pleiss, J., Molecular mechanism of deactivation of C. antarctica lipase B by methanol. J. Biotechnol. 2013, 168, 462-469.
39. Bell, G., Janssen, A. E. M., Halling, P. J., Water activity fails to predict critical hydration level for enzyme activity in polar organic solvents: Interconversion of water concentrations and activities. Enzyme Microb. Technol. 1997, 20, 471-477.
40. Castillo, E., Torres-Gavilan, A., Sandoval, G., Marty, A., Thermodynamical methods for the optimization of lipase-catalyzed reactions. Methods Mol. Biol. 2012, 861, 383-400.
41. Al-Zuhair, S., Ling, F. W., Jun, L. S., Proposed kinetic mechanism of the production of biodiesel from palm oil using lipase. Process Biochem. 2007, 42, 951-960.
42. Lousa, D., Baptista, A. M., Soares, C. M., Analyzing the molecular basis of enzyme stability in ethanol/water mixtures using molecular dynamics simulations. J. Chem. Inf. Model. 2012, 52, 465-473.
43. Liu, W., Bratko, D., Prausnitz, J. M., Blanch, H. W., Effect of alcohols on aqueous lysozyme-lysozyme interactions from static light-scattering measurements. Biophys. Chem. 2004, 107, 289-298.
44. Yamazaki, K., Iwura, T., Ishikawa, R., Ozaki, Y., Methanol-induced tertiary and secondary structure changes of granulocyte-colony stimulating factor. J. Biochem. 2006, 140, 49-56.
45. Graber, M., Irague, R., Rosenfeld, E., Lamare, S. et al., Solvent as a competitive inhibitor for Candida antarctica lipase B. Biochim Biophys Acta 2007, 1774, 1052-1057.
46. Noureddini, H., Gao, X., Philkana, R. S., Immobilized Pseudomonas cepacia lipase for biodiesel fuel production from soybean oil. Bioresour. Technol. 2005, 96, 769-777.
47. Chen, Y., Xiao, B., Chang, J., Fu, Y. et al., Synthesis of biodiesel from waste cooking oil using immobilized lipase in fixed bed reactor. Energy Convers. Manage. 2009, 50, 668-673.
48. Zhang, B., Weng, Y., Xu, H., Mao, Z., Enzyme immobilization for biodiesel production. Appl. Microbiol. Biotechnol. 2012, 93, 61-70.
49. Franssen, M. C., Steunenberg, P., Scott, E. L., Zuilhof, H., Sanders, J.P., Immobilised enzymes in biorenewables production. Chem. Soc. Rev. 2013, 42, 6491-6533.
50. Yan, Y., Li, X., Wang, G., Guanlin, L. et al., Biotechnological preparation of biodiesel and its high-valued derivatives: A review. Appl. Energy 2014, 113, 1614-1631.
51. Hwang, H. T., Qi, F., Yuan, C., Zhao, X. et al., Lipase-catalyzed process for biodiesel production: Protein engineering and lipase production. Biotechnol. Bioeng. 2014, 111, 639-653.
52. Invernizzi, G., Papaleo, E., Grandori, R., De, G. L., Lotti, M., Relevance of metal ions for lipase stability: structural rearrangements induced in the Burkholderia glumae lipase by calcium depletion. J. Struct. Biol. 2009, 168, 562-570.
53. Gog, A., Roman, M., Toça, M., Paizs, C., Irimie, D. F., Biodiesel production using enzymatic transesterification - current state and perspectives. Renew. Energ. 2012, 39, 10-16.
54. Chen, J. W., Wu, W. T., Regeneration of immobilized Candida antarctica lipase for transesterification. J. Biosci. Bioeng. 2003, 95, 466-469.
55. Nelson, L., Foglia, T., Marmer, W., Lipase-catalyzed production of biodiesel. J. Am. Oil Chem. Soc. 1996, 73, 1191-1195.
56. Soumanou, M. M., Bornscheuer, U. T., Improvement in lipase-catalyzed synthesis of fatty acids methyl esters from sunflower oil. Enzyme Microb. Technol. 2003, 33, 97-103.
57. Dossat, V., Combes, D., Marty, A., Continuous enzymatic transesterification of high oleic sunflower oil in a packed bed reactor: influence of the glycerol production. Enzyme Microb. Technol. 1999, 25, 194-200.
58. Caballero, V., Bautista, F. M., Campelo, J. M., Luna, D. et al., Sustainable preparation of a novel glycerol-free biofuel by using pig pancreatic lipase: Partial 1, 3-regiospecific alcoholysis of sunflower oil. Process. Biochem. 2009, 334-342.
59. Freitas, L., Paula, A. V., dos Santos, J. C., Zanin, G. M., de Castro, H. F., Enzymatic synthesis of monoglycerides by esterification reaction using Penicillium camembertii lipase immobilized on epoxy SiO2-PVA composite. J. Mol. Catal. B Enzym. 2010, 65, 87-90.
60. Stepan, E., Velea, S., Tanase, C., Raud, A. et al., Biodiesel and surfactants from fats. Rev. Chim. 2012, 63, 646-650.
61. Royon, D., Daz, M., Ellenrieder, G., Locatelli, S., Enzymatic production of biodiesel from cotton seed oil using t-butanol as a solvent. Bioresour. Technol. 2007, 98, 648-653.
62. Iso, M., Chen, B., Eguchi, M., Kudo, T., Shrestha, S., Production of biodiesel fuel from triglycerides and alcohol using immobilized lipase. J. Mol. Catal. B Enzym. 2001, 16, 53-58.
63. Du, W., Li, W., Sun, T., Chen, X., Liu, D., Perspectives for biotechnological production of biodiesel and impacts. Appl. Microbiol. Biotechnol. 2008, 79, 331-337.
64. Li, L. L., Du, W., Liu, D. H., Wang, L., Li, Z. B., Lipase-catalyzed transesterification of rapeseed oils for biodiesel production with a novel organic solvent as the reaction medium. Mol. Catal. B Enzym. 2006, 43, 58-62.
65. Shimada, Y., Watanabe, Y., Sugihara, A., Tominaga, Y., Enzymatic alcoholysis for biodiesel fuel production and application of the reaction to oil processing. J. Mol. Catal. B Enzym. 2002, 17, 133-142.
66. Xu, Y., Nordblad, M., Woodley, J. M, A two-stage enzymatic ethanol-based biodiesel production in a packed bed reactor. J. Biotechnol. 2012, 162, 407-414.
67. Watanabe, Y., Shimada, Y., Sugihara, A., Noda, H. et al., Continuous production of biodiesel fuel from vegetable oil using immobilized Candida antarctica lipase. J. Am. Oil Chem. Soc. 2000, 77, 355-360.
68. Hernandez-Martin, E., Otero, C., Different enzyme requirements for the synthesis of biodiesel: Novozym 435 and Lipozyme TL IM. Bioresour. Technol. 2008, 99, 277-286.
69. Talukder, M. M. R., Beatrice, K. L. M., Song, O. P., Puah, S. Y. et al., Improved method for efficient production of biodiesel from palm oil. Energ. Fuel 2008, 22, 141-144.
70. Hama, S., Kondo, A., Enzymatic biodiesel production: an overview of potential feedstocks and process development. Bioresour. Technol. 2013, 135, 386-395.
71. Lee, J. H., Kwon, C. H., Kang, J. W., Park, C. et al., Biodiesel production from various oils under supercritical fluid conditions by Candida antartica lipase B using a stepwise reaction method. Appl. Biochem. Biotechnol. 2009, 156, 24-34.
72. Ha, S. H., Lan, M. N., Lee, S. H., Hwang, S. M., Koo, Y. M., Lipase-catalyzed biodiesel production form soybean oil in ionic liquids. Enzyme Microb. Technol. 2007, 41, 480-483.
73. Rao, N., Lutz, S., Wurgws, K., Minor, D., Continuous biocatalytic processes. Org. Process Res. Dev. 2009, 13, 607-613.
74. Freitas, L., dos Santos, J. C., Zanin, G. M., de Castro, H. F., Packed-bed reactor running on babassu oil and glycerol to produce monoglycerides by enzymatic route using immobilized Burkholderia cepacia lipase. Appl. Biochem. Biotechnol. 2010, 161, 372-381.
75. Halim, S. F., Kamaruddin, A. H., Fernando, W. J., Continuous biosynthesis of biodiesel from waste cooking palm oil in a packed bed reactor: optimization using response surface methodology (RSM) and mass transfer studies. Bioresour. Technol. 2009, 100, 710-716.
76. Severac, E., Galy, O., Turon, F., Pantel, C. A. et al., Selection of CalB immobilization method to be used in continuous oil transesterification: analysis of the economical impact. Enzyme Microb. Technol. 2011, 48, 61-70.
77. Severac, E., Galy, O., Turon, F., Monsan, P., Marty, A., Continuous lipase-catalyzed production of esters from crude high-oleic sunflower oil. Bioresour. Technol. 2011, 102, 4954-4961.
78. Yoshida, A., Hama, S., Tamadani, N., Fukuda, H., Kondo, A., Improved performance of a packed-bed reactor for biodiesel production through whole-cells biocatalysis employing a high-lipase-expression system. Biochem. Eng. J. 2012, 63, 76-80.
79. Hajar, M., Shokrollahzadeh, S., Vahabzadeh, F., Monozzami, A., Solvent-free methanolysis of canola oil in a packed-bed reactor with use of Novozym 435 plus loofa. Enzyme Microb. Technol. 2009, 188, 188-194.
80. Dizge, N., Keskinler, B., Tanriseven, A., Biodiesel production from canola oil by using lipase immobilized onto hydrophobic microporous styrene-divinylbenzene copolymer. Biochem. Eng. J. 2009, 44, 220-225.
81. Sang-Min, Y., Yong-Cheol, P., Kyungmoon, P., Effect of environmental conditions and methanol feeding strategy on lipase-mediated biodiesel production using soybean oil. Biotechnol. Bioprocess Eng. 2010, 15, 614-619.
82. Machsun, A. L., Gozna, M., Nasikin, M., Setyahadi, S., Yoo, Y. J., Membrane microreactor in biocatalytic transesterification of triolein for biodiesel production. Biotechnol. Bioprocess Eng. 2010, 15, 911-916.
83. Rodrigues, R. C., Pessela, B. C., Volpato, G., Fernández-Lafuente, R. et al., Two step ethanolysis: A simple and efficient way to improve the enzymatic biodiesel synthesis catalyzed by an immobilized-stabilized lipase from Thermomyces lanuginosus. Process Biochem. 2010, 45, 1268-1273.
84. Wang, X., Liu, X., Zhao, C., Ding, Y., Xu, P., Biodiesel production in packed-bed reactors using lipase-nanoparticle biocomposite. Bioresour. Technol. 2011, 102, 6352-6355.
85. Dors, G., Freitas, L., Mendes, A. A., Furigo, A., de Castro, H. F., Transesterification of palm oil catalyzed by Pseudomonas fluorescens lipase in a packed-bed reactor. Energ. Fuel 2012, 26, 5977-5982.
86. Chattopadhyay, S., Sen, R., Development of a novel integrated continuous reactor system for biocatalytic production of biodiesel. Bioresour. Technol. 2013, 147, 395-400.