Deep eutectic solvents: Promising solvents and nonsolvent solutions for biocatalysis

Environmentally Friendly Syntheses Using Ionic Liquids

Volumn , Issue , 2014, Pages 67-86

  de María, Pablo Domínguez ^a  

^a NONE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CELL ENGINEERING; MOLECULAR BIOLOGY;

ADDED VALUES; DEEP EUTECTIC SOLVENTS; GENETIC DESIGN; INDUSTRIAL REACTIONS; INDUSTRIAL SYNTHESIS; NON-SOLVENTS; OPTICALLY ACTIVE COMPOUNDS; OVER-EXPRESSION;

ENZYMES;

EID: 85054463722     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1201/b17508     Document Type: Chapter

References (75)

1. Abbott, A.P., Boothby, D., Capper, G., Davies, D.L., and Rasheed, R.K. 2004. Deep eutectic solvents formed between choline chloride and carboxylic acids: versatile alternatives to ionic liquids. J. Am. Chem. Soc. 126: 9142-9147.
2. Abbott, A.P., Capper, G., Davies, D.L., Rasheed, R.K., and Tambyrajah, V. 2003. Novel solvent properties of choline chloride/urea mixtures. Chem. Commun. 70-71.
3. Abbott, A.P., Cullis, P.M., Gibson, M.J., Harris, R.C., and Raven, E. 2007. Extraction of glycerol from biodiesel into a eutectic based ionic liquid. Green Chem. 9: 868-872.
4. Abbott, A.P., Harris, R.C., Ryder, K.S., D'Agostino, C., Gladden, L.F., and Mantle, M.D. 2011. Glycerol eutectics as sustainable solvent systems. Green Chem. 13: 82-90.
5. Attri, P., Venkatesu, P., Kumar, A., and Byrne, N. 2011. A protic ionic liquid attenuates the deleterious actions of urea on a-chymotrypsin. Phys. Chem. Chem. Phys. 13: 17023-17026.
6. Blusztajn, J.K. 1998. Choline, a vital amine. Science 281: 794-795.
7. Bornscheuer, U.T., Huisman, G., Kazlauskas, R.J., Lutz, S., Moore, J., and Robins, K. 2012. Engineering the third wave in biocatalysis. Nature 485: 185-194.
8. Carriazo, D., Serrano, M.C., Gutierrez, M.C., Ferrer, M.L., and del Monte, F. 2012. Deep-eutectic solvents playing multiple roles in the synthesis of polymers and related materials. Chem. Soc. Rev. 41: 4996-5014.
9. Choi, Y.H., van Spronsen, J., Dai, Y., Verberne, M., Hollmann, F., Arends, I.W.C.E., Witkamp, G.J., and Verpoorte, R. 2011. Are natural deep eutectic solvents the missing link in understanding cellular metabolism and physiology? Plant. Physiol. 156: 1701-1705.
10. Deetlefs, M., and Seddon, K.R. 2010. Assessing the greenness of some typical laboratory ionic liquids preparations. Green Chem. 12: 17-30.
11. Domínguez de María, P. 2008. Non-solvent applications of ionic liquids in biontransformations and organocatalysis. Angew. Chem. Int. Ed. 47: 6960-6968.
12. Domínguez de María, P. 2011. Recent developments in the biotechnological production of hydrocarbons: paving the way for bio-based platform chemicals. ChemSusChem 4: 327-329.
13. Domínguez de María, P., ed. 2012. Ionic liquids in biotransformations and organocatalysis: solvents and beyond. John Wiley & Sons, Hoboken, NJ.
14. Domínguez de María, P., and Martinsson, A. 2009. Ionic-liquid-based method to determine the degree of esterification in cellulose fibers. Analyst 134: 493-496.
15. Domínguez de María, P., and Maugeri, Z. 2011. Ionic liquids in biotransformations: from proof-of-concept to emerging deep-eutectic-solvents. Curr. Opin. Chem. Biol. 15: 220-225.
16. Drauz, K.H., Gröger, H., and May, O. 2012. Enzyme catalysis in organic synthesis. Wiley-VCH, Weinheim
17. Durand, E., Lecomte, J., Baréa, B., Piombo, G., Dubreucq, E., and Villeneuve, P 2012. Evaluation of deep eutectic solvents as new media for Candida antarctica B lipase catalyzed reactions. Process. Biochem. 47: 2081-2089.
18. Faber, K. 2008. Biotransformations in organic synthesis. Springer, Berlin.
19. Falcioni, F., Housden, H.R., Ling, Z., Shimizu, S., Walker, A.J. and Bruce, N.C. 2010. Soluble, folded and active subtilisin in a protic ionic liquid. Chem. Commun. 46: 749-751.
20. Fernández-Álvaro, E., and Domínguez de María, P. 2012. Ionic liquids in biocatalytic oxidations: from non-conventional media to non-solvent applications. Curr. Org. Chem. 16: 2492-2507.
21. Francisco, M., van den Bruinhorst, A., and Kroon, M.C. 2012. New natural and renewable low transition temperature mixtures (LTTMs): screening as solvents for lignocellulose biomass processing. Green Chem. 14: 2153-2157.
22. Fukaya, Y., Lizuka, Y., Sekihawa, K., and Ohno, H. 2007. Bio ionic liquids: room temperature ionic liquids composed wholly of biomaterials. Green Chem. 9: 1155-1157.
23. Gambino, M., Gaune, P., Nabavian, M., Gaune-Escard, M., and Bros, J.P. 1987. Enthalpie de fusion de l'uree et de quelques melanges eutectiques a base d'uree. Thermochim. Acta 111: 37-47.
24. Gamenara, D., Seoane, G., Saenz Méndez, P., and Domínguez de María, P. 2012. Redox biocatalysis: fundamentals and applications. John Wiley & Sons, Hoboken, NJ.
25. Gill, I., and Valivety, R. 2002. Pilot-scale enzymatic synthesis of bioactive oligopeptides in eutectic-based media. Org. Proc. Res. Dev. 6:684-691.
26. Gill, I., and Vulfson, E.N. 1993. Enzymatic synthesis of short peptides in heterogeneous mixtures of substrates. J. Am. Chem. Soc. 115: 3348-3349.
27. Gill, I., and Vulfson, E. 1994. Enzymic catalysis in heterogeneous eutectic mixtures of substrates. Trends Biotechnol. 12: 118-122.
28. Gorke, J.T., Kazlauskas, R.J., and Srienc, F. 2009. Enzymatic processing in deep eutectic solvents. US2009/0117628.
29. Gorke, J.T., Srienc, F., and Kazlauskas, R.J. 2008. Hydrolase-catalyzed biotransformations in deep eutectic solvents. Chem. Commun. 1235-1237.
30. Gorke, J., Srienc, F., and Kazlauskas, R.J. 2010. Toward advanced ionic liquids. Polar enzyme-friendly solvents for biocatalysis. Biotechnol. Bioprocess. Eng. 15: 40-53.
31. Grande, P.M., Bergs, C., and Domínguez de María, P. 2012. Chemo-enzymatic conversion of glucose into 5-hydroxymethylfurfural in seawater. ChemSusChem 5: 1203-1206.
32. Gutiérrez, M.C., Ferrer, M.L., Yuste, L., Rojo, F., and del Monte, F. 2010. Bacteria incorporation in deep eutectic solvents through freeze-drying. Angew. Chem. Int. Ed. 49: 2158-2162.
33. Hayyan, M., Hashim, M.A., Hayvan, A., Al-Saadi, M.A., AlNashef, I.M., Mirghani, M.E.S., and Saheed, O.K. 2013. Are deep eutectic solvents benign or toxic? Chemosphere 90: 2193-2195.
34. Hayyan, M., Mjalli, F.S., Ali Hashim, M., and AlNashef, I.M. 2010. A novel technique for separating glycerine from palm oil-based biodiesel using ionic liquids. Fuel Proc. Technol. 91: 116-120.
35. Hernáiz, M.J., Alcántara, A.R., Garcia, J.I., and Sinisterra, J.V. 2010. Applied biotransformations in green solvents. Chem. Eur. J. 16: 9422-9437.
36. Hertel, R.M., Bommarius, A.S., Realff, M.J., and Kang, Y. 2012. Deep eutectic solvent systems and methods. W02012/145522.
37. Jakoblinnert, A., Mladenov, R., Paul, A., Sibilla, F., Schwaneberg, U., Ansorge-Schumacher, M.B., and Dominguez de Maria, P. 2011. Asymmetric reduction of ketones with recombinant E. coli whole cells in neat substrates. Chem. Commun. 47: 12230-12232.
38. Jorba, X., Gill, I., and Vulfson, E.N. 1995. Enzymatic synthesis of the delicious peptide fragments in eutectic mixtures. J. Agric. Food Chem. 43: 2536-2541.
39. Klibanov, A.M. 2001. Improving enzymes by using them in organic solvents. Nature 409: 241-246.
40. Krystof, M., Pérez-Sánchez, M., and Domínguez de María, P. 2013. Lipase-catalyzed (trans)esterification of 5-hydroxymethylfurfural and separation of HMF-esters using deep-eutectic-solvents. ChemSusChem. 6: 630-634.
41. Lehmann, C., Sibilla, F., Maugeri, Z., Streit, W.R., Dominguez de Maria, P., Martinez, R., and Schwaneberg, U. 2012. Reengineering CelA2 cellulase for hydrolysis in aqueous solutions of deep eutectic solvents and concentrated seawater. Green Chem. 14: 2719-2726.
42. Liese, A., Seelbach, K., and Wandrey, C. 2006. Industrial biotransformations. 2nd ed. Wiley-VCH, Weinheim.
43. Lindberg, D., de la Fuente Revenga, M., and Widersten, M. 2010. Deep eutectic solvents are viable cosolvents for enzyme-catalyzed epoxide hydrolysis. J. Biotechnol. 147: 169-171.
44. López-Fandino, R., Gill, I., and Vulfson, E.N. 1994a. Enzymatic catalysis in heterogeneous mixtures of substrates: the role of the liquid phase and the effects of "adjuvants." Biotechnol. Bioeng. 43: 1016-1023.
45. López-Fandino, R., Gill, I., and Vulfson, E.N. 1994b. Protease-catalyzed synthesis of oligopeptides in heterogeneous substrate mixtures. Biotechnol. Bioeng. 43: 1024-1030.
46. Lozano, P. 2010. Enzymes in neoteric solvents: from one-phase to multiphase systems. Green Chem. 12: 555-569.
47. Lozano, P., Bernal, B., Bernal, J.M., Pucheault, M., and Vaultier, M. 2011. Stabilizing immobilized cellulase by ionic liquids for saccharification of cellulose solutions in 1-butyl-3-methylimidazolium chloride. Green Chem. 13: 1406-1410.
48. Lozano, P., Bernal, J.M., and Navarro, A. 2012a. A clean enzymatic process for producing flavor esters by direct esterification in switchable ionic liquid/solid phases. Green Chem. 14: 3026-3033.
49. Lozano, P., Bernal, B., Recio, I., and Belleville, M.P. 2012b. A cyclic process for full enzymatic saccharification of pretreated cellulose with full recovery and reuse of the ionic liquid 1-butyl-3-methylimidazolium chloride. Green Chem. 14: 2631-2637.
50. Maugeri, Z., and Domínguez de María, P. 2012. Novel choline-chloride-based deep eutectic solvents with renewable hydrogen bond donors: levulinic acid and sugar-based polyols. RSC Adv. 2: 421-425.
51. Maugeri, Z., Leitner, W., and Domínguez de María, P. 2012. Practical separation of alcohol-ester mixtures using deep eutectic solvents. Tetrahedron Lett. 53: 6968-6971.
52. Mutti, F.G., and Kroutil, W. 2012. Asymmetric bio-amination of ketones in organic solvents. Adv. Synth. Catal. 354: 3409-3413.
53. Pace, V., Hoyos, P., Castoldi, L., Domínguez de María, P., and Alcántara, A.R. 2012. 2-Methyltetrahydrofuran (2-MeTHF): a biomass-derived solvent with broad application in organic chemistry. ChemSusChem 5: 1369-1379.
54. Pang, K., Hou, Y., Wu, W., Guo, W., Peng, W., and Marsh, K.N. 2012. Efficient separation of phenols from oils via forming deep eutectic solvents. Green Chem. 14: 2398-2401.
55. Pérez-Sánchez, M., Sandoval, M., Hernáiz, M.J., and Domínguez de María, P. 2013. Biocatalysis in biomass-derived solvents: the quest for fully sustainable chemical processes. Curr. Org. Chem. 17: 1188-1199.
56. Rastogi, R.P., and Bassi, P.S. 1964. Mechanism of eutectic crystallization. J. Phys. Chem. 68: 2398-2406.
57. Reetz, M.T. 2011. Laboratory evolution of stereoselective enzymes: a prolific source of catalysts for asymmetric reactions. Angew. Chem. Int. Ed. 50: 138-174.
58. Reetz, M.T. 2012. Laboratory evolution of stereoselective enzymes as a means to expand the toolbox of organic chemistrs. Tetrahedron 68: 7530-7548.
59. Rose, M., and Palkovits, R. 2012. Isosorbide as a renewable platform chemical for versatile applications—quo vadis? ChemSusChem 9: 167-176.
60. Ruβ, C., and König, B. 2012. Low melting mixtures in organic synthesis—an alternative to ionic liquids? Green Chem. 14: 2969-2982.
61. Savile, C.K., Janey, J.M., Mundorff, E.C., Moore, J.C., Tam, S., Jarvis, W.R., Colbeck, J.C., et al. 2010. Biocatalytic asymmetric synthesis of chiral amines from ketones applied to sitagliptin manufacture. Science 329: 305-309.
62. Shahbaz, K., Mjalli, F.S., Hashim, M.A., and AlNashef, I.M. 2010. Using deep eutectic solvents for the removal of glycerol from palm oil-based biodiesel. J. App. Sci. 10: 3349-3354.
63. Shahbaz, K., Mjalli, F.S., Hashim, M.A., and AlNashef, I.M. 2011a. Using deep eutectic solvents based on methyl triphenyl phosphonium bromide for the removal of glycerol from palm-oil-based biodiesel. Energy Fuels 25: 2671-2678.
64. Shahbaz, K., Mjalli, F.S., Hashim, M.A., and AlNashef, I.M. 2011b. Eutectic solvents for the removal of residual palm oil-based biodiesel catalyst. Sep. Purif. Technol. 81: 216-222.
65. Truppo, M.D., Strotman, H., and Hughes, G. 2012. Development of an immobilized transaminase capable of operating in organic solvent. ChemCatChem 4: 1071-1074.
66. van Putten, R.J., van der Waal, J.C., de Jong, E., Rasrendra, C.B., Heeres, H.J., and de Vries, J.G. 2013. Hydroxymethylfurfual, a versatile platform chemical made from renewable resources. Chem. Rev. DOI: 10.1021/cr300182k.
67. van Spronsen, J., Witkamp, G.J., Hollmann, F., Choi, Y.H., and Verpoorte, R. 2011. Process for extracting materials from biological material. W02011/155829.
68. Wasserscheid, P., and Welton, T. 2007. Ionic liquids in synthesis. Wiley-VCH, Weinheim.
69. Welton, T. 1999. Room-temperature ionic liquids. Chem. Rev. 99: 2071-2084.
70. Whittall, J., and Sutton, P. 2009, 2012. Practical methods for biocatalysis and biotransformations. 2 vols. Wiley-VCH, Weinheim.
71. Zhang, Q., De Oliveria Vigier, K., Royer, S., and Jerome, F. 2012. Deep eutectic solvents: syntheses, properties and applications. Chem. Soc. Rev. 41: 7108-7146.
72. Zhao, H., and Baker, G.A. 2013. Ionic liquids and deep eutectic solvents for biodiesel synthesis: a review. J. Chem. Technol. Biotechnol. 88: 3-12.
73. Zhao, H., Baker, G.A., and Holmes, S. 2011a. New eutectic ionic liquids for lipase activation and enzymatic preparation of biodiesel. Org. Biomol. Chem. 9: 1908-1916.
74. Zhao, H., Baker, G.A., and Holmes, S. 2011b. Protease activation in glycerol-based deep eutectic solvents. J. Mol. Cat. B Enzym. 72: 163-167.
75. Zhao, H., Zhang, C., and Crittle, T.D. 2013. Choline-based deep eutectic solvents for enzymatic preparation of biodiesel from soybean oil. J. Mol. Cat. B Enzym. 85-86: 243-247.