Native lipase dissolved in hydrophilic green solvents: A versatile 2-phase reaction system for high yield ester synthesis

European Journal of Lipid Science and Technology

Volumn 117, Issue 2, 2015, Pages 167-177

  Kleiner, Beatrice ^a   Schörken, Ulrich ^a  

^a Faculty of Applied Natural Sciences   (Germany)

Author keywords

Deep eutectic solvents; Emollients; Esterification; Green solvents; Lipase

Indexed keywords

CANDIDA ANTARCTICA;

EID: 84922774531     PISSN: 14387697     EISSN: 14389312     Source Type: Journal    
DOI: 10.1002/ejlt.201400494     Document Type: Article

References (33)

1. Zaks, A., Klibanov, A. M., Enzymatic catalysis in organic media at 100 degrees C. Science 1984, 224, 1249-1251.
2. Zaks, A., Klibanov, A. M., Enzyme-catalyzed processes in organic solvents. Proc. Natl. Acad. Sci. USA 1985, 82, 3192-3196.
3. Bornscheuer, U. T., Kazlauskas, R. J., Hydrolases in Organic Synthesis: Regio- and Stereoselective Biotransformations, Wiley-VCH, Weinheim 1999.
4. Jaeger, K.-E., Eggert, T., Lipases for biotechnology. Curr. Opin. Biotechnol. 2002, 13, 390-397.
5. Villeneuve, P., Lipases in lipophilization reactions. Biotechnol. Advances 2007, 25, 515-536.
6. Dominguez de Maria, P., Maugeri, Z., Ionic liquids in biotransformations: From proof-of-concept to emerging deep-eutectic-solvents. Curr. Opin. Chem. Biol. 2011, 15, 220-225.
7. Kobayashi, T., Lipase-catalyzed syntheses of sugar esters in non-aqueous media. Biotechnol. Lett. 2011, 33, 1911.
8. Adlercreutz, P., Immobilisation and application of lipases in organic media. Chem. Soc. Rev. 2013, 42, 6406-6436.
9. Gu, Y., Jerome, F., Glycerol as a sustainable solvent for green chemistry. Green Chem. 2010, 12, 1127-1138.
10. Diaz-Alvarez, A. E., Francos, J., Lastra-Barreira, B., Crochet, P., Cadierno, V., Glycerol and derived solvents: New sustainable reaction media for organic synthesis. Chem. Commun. 2011, 47, 6208-6227.
11. Oua, G., Hea, B., Yuan, Y., Lipases are soluble and active in glycerol carbonate as a novel biosolvent. Enz. Microb. Technol. 2011, 49, 167-170.
12. Wolfson, A., Atyya, A., Dlugy, C., Glycerol triacetate as solvent and acyl donor in the production of isoamyl acetate with Candida antarctica lipase B. Bioprocess. Biosyst. Eng. 2010, 33, 363-366.
13. Wolfson, A., Yefet, E., Alon, T., Dlugy, C., Tavor, D., Glycerolysis of Esters with Candida antarctica Lipase B in Glycerol. J. Adv. Chem. Eng. 2011, 1, A110403. 5 pp. DOI: 10.4303/jace/A110403
14. Watanabe, Y., Nagao, T., Nishida, Y., Takagi, Y., Shimada, Y., Enzymatic production of fatty acid methyl esters by hydrolysis of acid oil followed by esterification. J. Am. Oil Chem. Soc. 2007, 84, 1015-1021.
15. Xu, Y., Nordblad, M., Nielsen, P. M., Brask, J., Woodley, J. M., In situ visualization and effect of glycerol in lipase-catalyzed ethanolysis of rapeseed oil. J. Mol. Catal. B: Enzym. 2011, 72, 213-219.
16. Durand, E., Lecomte, J., Baréa, B., Piombo, G. E., et al. Evaluation of deep eutectic solvents as new media for Candida antarctica B lipase catalyzed reactions. Process Biochem. 2012, 47, 2081-2089.
17. Abbott, A. P., Capper, G., Davies, D. L., Rasheed, R. K., Tambyrajah, V., Novel solvent properties of choline chloride/urea mixtures. Chem. Commun. 2003, 1, 70-71.
18. Gorke, J. T., Srienc, F., Kazlauskas, R. J., Hydrolase-catalyzed biotransformations in deep eutectic solvents. Chem. Commun. 2008, 10, 1235-1237.
19. Gorke, J. T., Srienc, F., Kazlauskas, R. J., Deep Eutectic Solvents for Candida Antarctica. ACS Symposium Series 2010, 1038, 169-180.
20. Zhao, H., Baker, G. A., Holmes, S., New eutectic ionic liquids for lipase activation and enzymatic preparation of biodiesel. Org. Biomol. Chem. 2011, 9, 1908-1916.
21. Zhao, H., Zhang, C., Crittle, T. D., Choline-based deep eutectic solvents for enzymatic preparation of biodiesel from soybean oil. J. Mol. Catal. B: Enzym. 2013, 85-86, 243-247.
22. Durand, E., Lecomte, J., Barea, B., Dubreucq, E., et al. Evaluation of deep eutectic solvent-water binary mixtures for lipase-catalyzed lipophilization of phenolic acids. Green Chem. 2013, 15, 2275-2282.
23. Durand, E., Lecomte, J., Baréa, B., Villeneuve, P., Towards a better understanding of how to improve lipase catalyzed reactions using deep eutectic solvents based on choline chloride. Eur. J. Lipid Sci. Technol. 2014, 116, 16-23.
24. Hills, G., Industrial use of lipases to produce fatty acid esters. Eur. J. Lipid Sci. Technol. 2003, 105, 601-607.
25. Ansorge-Schumacher, M. B., Thum, O., Immobilised lipases in the cosmetics industry. Chem. Soc. Rev. 2013, 42, 6475-6490.
26. Thum, O., Oxenbøll, K. M., Biocatalysis-A sustainable method for the production of emollient esters. SOFW Journal 2008, 134, 44-47.
27. Schörken, U., Kempers, P., Lipid biotechnology: Industrially relevant production processes. Eur. J. Lipid Sci. Technol. 2009, 111, 627-645.
28. Busch, S., Horlacher, P., Both, S., Westfechtel, A., Schörken, U., Green synthesis routes toward triglycerides of conjugated linoleic acid. Eur. J. Lipid Sci. Technol. 2011, 113, 92-99.
29. Secundo, F., Carrea, G., Soregaroli, C., Varinelli, D., Morrone, R., Activity of different Candida antarctica lipase B formulations in organic solvents. Biotechnol. Bioeng. 2001, 73, 157-163.
30. Valivety, R. H., Johnston, G. A., Suckling, C. J., Halling, P. J., Solvent effects on biocatalysis in organic systems: Equilibrium position and rates of lipase catalyzed esterification. Biotech. Bioeng. 1991, 38, 1137-1143.
31. Naik, S., Basu, A., Saikia, R., Madan, B., et al. Lipases for use in industrial biocatalysis: Specificity of selected structural groups of lipases. J. Mol. Catal. B: Enz. 2010, 65, 18-23.
32. Monhemi, H., Housaindokht, M. R., Moosavi-Movahedi, A. A., Bozorgmehr, M.-R., How a protein can remain stable in a solvent with high content of urea: Insights from molecular dynamics simulation of Candida antarctica lipase B in urea: Choline chloride deep eutectic solvent. Phys. Chem. Chem. Phys. 2014, 16, 14882-14893.
33. Gruber, C. C., Pleiss, J., Lipase B from Candida antarctica binds to hydrophobic substrate-water interfaces via hydrophobic anchors surrounding the active site entrance. J. Mol. Catal. B: Enz. 2012, 84, 48-54.