DOI QR코드

DOI QR Code

Applications and Prospects of Ionic Liquids in Microbiology and Biochemical Engineering

이온성액체의 미생물.생명화학공학에의 응용과 전망

  • Ha, Sung Ho (Department of Chemical Engineering and Nano-Bio Technology, Hannam University)
  • 하성호 (한남대학교 나노생명화학공학과)
  • Received : 2012.11.08
  • Accepted : 2012.11.25
  • Published : 2013.03.28

Abstract

Ionic liquids (ILs) have been widely recognized as environmentally benign solvents. Their unique properties, including negligible vapor pressure, non-flammability, a wide liquid range and their tunable physicochemical properties by proper selection of cations and anions, make them attractive green solvents in a variety of fields such as organic synthesis/catalysis, extraction/ separation, and electrochemistry, amongst others. In this paper, the recent technological developments and their prospects in the application of ILs in microbiology and biochemical engineering, including enzymatic reactions, protein folding/refolding and biomass dissolution, are discussed.

비휘발성, 비폭발성, 열적 안정성의 특성을 가지고 있는 이온성액체는 환경친화적인 용매이고, 또한 양이온과 음이온의 다양한 조합을 통해 사용 목적에 부합하는 이온성액체를 용이하게 합성할 수 있어 용매로서의 다양성으로 인해 청정 용매, 촉매, 추출 및 분리, 전해질 등의 분야에서 다양하게 응용되고 있다. 이에 본 논문에서는 이온성액체에 대한 기본 지식와 함께 현재 미생물생명화학공정에서 이온성액체가 용매로서 효과적으로 응용되고 있는 효소반응 분야, 단백질 재접힘 분야, 바이오매스 용해 및 활용분야에서의 최근 연구동향을 기술하였다.

Keywords

References

  1. Bae, S. -W., W. -J. Chang, Y. -M. Koo, and S. H. Ha. 2012. Enhanced refolding of lysozyme with imidazolium-based room temperature ionic liquids: Effect of hydrophobicity and sulfur residue. Sci. China Chem. 55: 1657-1662. https://doi.org/10.1007/s11426-012-4678-7
  2. Barthel, S. and T. Heinze. 2006. Acylation and carbanilation of cellulose in ionic liquids. Green Chem. 8: 301-306. https://doi.org/10.1039/b513157j
  3. Chiappe, C., E. Leandri, S. Lucchesi, and D. Pieraccini. 2004. Biocatalysis in ionic liquids: The stereoconvergent hydrolysis of trans-β-methylstyrene oxide catalyzed by soluble epoxide hydrolase. J. Mol. Catal. B: Enzym. 27: 243-248. https://doi.org/10.1016/j.molcatb.2003.12.008
  4. Eckstein, M., P. Wasserscheid, and U. Kragl. 2002. Enhanced enantioselectivity of lipase from Pseudomonas sp. at high temperatures and fixed water activity in the ionic liquid 1- Butyl-3-methylimidazolium Bis[(trifluoromethyl)sulfonyl] amide. Biotechnol. Lett. 24: 763-767.
  5. Eckstein, M., M. V. Filho, A. Liese, and U. Kragl. 2004. Use of an ionic liquid in a two-phase system to improve an alcohol dehydrogenase catalysed reduction. Chem. Commun. 1084- 1085.
  6. El Sound, O. A., A. Koschella, L. C. Fidale, S. Dorn, and T. Heinze. 2007. Applications of ionic liquids in carbohydrate chemistry: A window of opportunities. Biomacromol. 8: 2629- 2647. https://doi.org/10.1021/bm070062i
  7. Erbeldinger, M., A. J. Mesiano, and A. J. Russel. 2000, Enzymatic catalysis of formation of Z-aspartame in ionic liquid- an alternative to enzymatic catalysis in organic solvents. Biotechnol. Prog. 16: 1129-1131. https://doi.org/10.1021/bp000094g
  8. Freemantle, M. 1998. Designer solvents - Ionic liquids may boost clean technology development. Chem. Eng. News 76: 32-37.
  9. Fukaya, Y., A. Sugimoto, and H. Ohno. 2006. Superior solubility of polysaccharides in low viscosity, polar and halogen-free 1,3-dialkylimidazolium formates. Biomacromol. 7: 3295-3297. https://doi.org/10.1021/bm060327d
  10. Fukaya, Y., K. Hayashi, M. Wada, and H. Ohno. 2008. Cellulose dissolution with polar ionic liquids under mild conditions. Green Chem. 10: 44-46. https://doi.org/10.1039/b713289a
  11. Ganske, F. and U. T. Bornscheuer. 2005. Lipase-catalyzed glucose fatty acid ester synthesis in ionic liquids. Org. Lett. 7: 3097-3098. https://doi.org/10.1021/ol0511169
  12. Ganske F. and U. T. Bornscheuer. 2005. Optimization of lipase-catalyzed glucose fatty acid ester synthesis in a twophase system containing ionic liquids and t-BuOH. J. Mol. Cat. B: Enzym. 36: 40-42. https://doi.org/10.1016/j.molcatb.2005.08.004
  13. Ha, S. H., M. N. Lan, S. H. Lee, S. M. Hwang, and Y. -M. Koo. 2007. Lipase-catalyzed biodiesel production from soybean oil in ionic liquids. Enzym. Microb. Technol. 41: 480-483. https://doi.org/10.1016/j.enzmictec.2007.03.017
  14. Ha, S. H., S. H. Lee, D. T. Dang, M. S. Kwon, W. -J. Chang, Y. J. Yu, I. S. Byun, and Y. -M. Koo. 2008. Enhanced stability of Candida antarctica lipase B in ionic liquids. Korean J. Chem. Eng. 25: 291-294. https://doi.org/10.1007/s11814-008-0051-0
  15. Ha, S. H., R. N. Menchavez, and Y. -M. Koo. 2010. Reprocessing of spent nuclear waste using ionic liquids. Korean J. Chem. Eng. 27: 1360-1365. https://doi.org/10.1007/s11814-010-0386-1
  16. Ha, S. H., N. L. Mai, and Y. -M. Koo. 2010. Butanol recovery from aqueous solution into ionic liquids by liquid-liquid extraction. Process Biochem. 45: 1899-1903. https://doi.org/10.1016/j.procbio.2010.03.030
  17. Hinckley, G., V. V. Mozhaev, C. Budde, and Y. L. Khmelnitsky. 2002. Oxidative enzymes possess catalytic activity in systems with ionic liquids. Biotechnol. Lett. 24: 2083-2087. https://doi.org/10.1023/A:1021305229969
  18. Kaftzik, N., P. Wasserscheid, and U. Kragl. 2002. Use of ionic liquids to increase the yield and enzyme stability in the β- galactosidase catalyzed synthesis of N-acetyllactosamine. Organ. Proc. Res. Dev. 6: 553-557. https://doi.org/10.1021/op0255231
  19. Kosan, B., C. Mitchels, and F. Meister. 2008. Dissolution and forming of cellulose with ionic liquids. Cellulose 15: 59-66.
  20. Kragl, U., N. Kaftzik, S. H. Schfer, M. Eckstein, P. Wasserscheid, and C. Hilgers. 2001. Enzyme catalysis in the presence of ionic liquids. Chem. Today 19: 22.
  21. Kragl, U., M. Eckstein, and N. Kaftzik. 2002. Enzyme catalysis in ionic liquids. Curr. Opin. Biotechnol. 13: 565-571. https://doi.org/10.1016/S0958-1669(02)00353-1
  22. Lange, C., G. Patil, and R. Rudolph. 2005. Ionic liquids as refolding additives: N'-alkyl and N'-(www-hydroxyalkyl) N-methylimidazolium chlorides. Protein Sci. 14: 2693-2701. https://doi.org/10.1110/ps.051596605
  23. Lee, J. K. and M. -J. Kim. 2002. Ionic liquid-coated enzyme for biocatalysis in organic solvent. J. Org. Chem. 67: 6845-6847. https://doi.org/10.1021/jo026116q
  24. Lee, S. H., T. T. N. Doan, S. H. Ha, and Y. -M. Koo. 2007. Using ionic liquids to stabilize lipase within sol-gel derived silica. J. Mol. Catal. B: Enzym. 45: 57-61. https://doi.org/10.1016/j.molcatb.2006.11.008
  25. Lee, S. H., T. T. N. Doan, S. H. Ha, W. -J. Chang, and Y. -M. Koo. 2007. Influence of ionic liquids as additives on sol-gel immobilized lipase. J. Mol. Catal. B: Enzym. 47: 129-134. https://doi.org/10.1016/j.molcatb.2007.05.002
  26. Lee, S. H., D. T. Dang, S. H. Ha, W. -J. Chang, and Y. -M. Koo. 2008. Lipase-catalyzed synthesis of fatty acid sugar ester using extremely supersaturated sugar solution in ionic liquids. Biotechnol. Bioeng. 99: 1-8. https://doi.org/10.1002/bit.21534
  27. Lee, S. H., T. V. Doherty, R. J. Linhardt, and J. S. Dordick. 2009. Ionic liquid-mediated selective extraction of lignin from wood leading to enhanced enzymatic cellulose hydrolysis. Biotechnol. Bioeng. 102: 1368-1376. https://doi.org/10.1002/bit.22179
  28. Liebert, T. and T. Heinze. 2008. Interactions of ionic liquids with polysaccharides. 5. Solvents and reaction media for the modification of cellulose. Biores. 3: 576-601.
  29. Lozano, P., T. de Diego, J. P. Guegan, M. Vaultier, and J. L. Iborra. 2001. Stabilization of α-chymotrypsin by ionic liquids in transesterification reactions. Biotechnol. Bioeng. 75: 563-569. https://doi.org/10.1002/bit.10089
  30. Lu, X., J. Hu, X. Yao, Z. Wang, and J. Li. 2006. Composite system based on chitosan and room-temperature ionic liquid: Direct electrochemistry and electrocatalysis of hemoglobin. Biomacromol. 7: 975-980. https://doi.org/10.1021/bm050933t
  31. Lu, X., Q. Zhang, L. Zhang, and J. Li. 2006. Direct electrontransfer of horseradish peroxidase and its biosensor based on chitosan and room temperature ionic liquid. Electrochem. Commun. 8: 874-878. https://doi.org/10.1016/j.elecom.2006.03.026
  32. Moniruzzaman, M., N. Kamiya, and N. Goto. 2010. Activation and stabilization of enzymes in ionic liquids. Org. Biomol. Chem. 8: 2887-2899. https://doi.org/10.1039/b926130c
  33. Moon, Y. H., S. M. Lee, S. H. Ha, and Y. -M. Koo. 2006. Enzyme-catalyzed reactions in ionic liquids. Korean J. Chem. Eng. 23: 247-263. https://doi.org/10.1007/BF02705724
  34. Mora-Pale, M., L. Meli, T. V. Doherty, R. J. Linhard, and J. S. Dordick. 2011. Room temperature ionic liquids as emerging solvents for the pretreatment of lignocellulosic biomass. Biotechnol. Bioeng. 108: 1229-1245. https://doi.org/10.1002/bit.23108
  35. Murugesan, S. and R. J. Linhardt. 2005. Ionic liquids in carbohydrate chemistry - Current trends and future directions. Curr. Org. Synth. 2: 437-451. https://doi.org/10.2174/157017905774322640
  36. Oliveira, G. B., L. B. Carvalho, and M. P. C. Silva. 2003. Properties of carbodiimide treated heparin. Biomaterials 24: 4777- 4783. https://doi.org/10.1016/S0142-9612(03)00376-4
  37. Parvulescu, V. I. and C. Hardacre. 2007, Catalysis in ionic liquids. Chem. Rev. 107: 2615-2665. https://doi.org/10.1021/cr050948h
  38. Phillips, D. M., L. F. Drummy, D. G. Conrady, D. M. Fox, R. R. Naik, M. O. Stone, P. C. Trulove, H. C. De Long, and R. A. Mantz. 2004. Dissolution and regeneration of Bombyx mori silk fibroin using ionic liquids. J. Am. Chem. Soc. 126: 14350- 14351. https://doi.org/10.1021/ja046079f
  39. Phillips, D. M., L. F. Drummy, R. R. Naik, H. C. De Long, D. M. Fox, P. C. Trulove, and R. A. Mantz. 2005. Regenerated silk fiber wet spinning from an ionic liquid solution. J. Mater. Chem. 15: 4206-4208. https://doi.org/10.1039/b510069k
  40. Poplin, J. H. R. P. Swatloski, J. D. Holbrey, S. K. Spear, A. Metlen, M. Grtzel, M. K. Nazeeruddin, and R. D. Rogers. 2007. Sensor technologies based on a cellulose supported platform. Chem. Commun. 2025-2027.
  41. Schfer, S. H., N. Kaftzik, P. Wasserscheid, and U. Kragl. 2001. Enzyme Catalysis in ionic liquids: Lipase-catalyzed kinetic resolution of 1-phenylethanol with improved enantioselectivity. Chem. Commun. 425-426.
  42. Sheldon, R. A., R. M. Lau, M. J. Sorgedrager, and F. van Rantwijk. 2002. Biocatalysis in ionic liquids. Green Chem. 4: 147-151. https://doi.org/10.1039/b110008b
  43. Simmons, T. J., S. H. Lee, J. Miao, M. Miyauchi, T. -J. Park, S. S. Bale, R. Pangule, J. Bult, J. G. Martin, J. S. Dordick, and R. J. Linhardt. 2011. Preparation of synthetic wood composites using ionic liquids. Wood Sci. Technol. 45: 719-733. https://doi.org/10.1007/s00226-010-0395-6
  44. Summers, C. A. and R. A. Flowers. 2000. Protein renaturation by the liquid organic salt ethylammonium nitrate. Protein Sci. 9: 2001-2008. https://doi.org/10.1110/ps.9.10.2001
  45. Sun N., M., Rahman, Y. Qin, M. L. Maxim, H. Rodriquez, and R. D. Rogers. 2009. Complete dissolution and partial delignification of wood in the ionic liquid 1-ethyl-3-methylimidazolium acetate. Green Chem. 11: 646-655. https://doi.org/10.1039/b822702k
  46. Swatloski, R. P., S. K. Spear, J. D. Holbrey, and R. D. Rogers. 2002. Dissolution of cellulose with ionic liquids. J. Am. Chem. Soc. 124: 4974-4975. https://doi.org/10.1021/ja025790m
  47. Tan, S. S. and D. R. MacFarlane. 2010. Ionic liquids in biomass processing. Top. Curr. Chem. 290: 311-339.
  48. Tadesse, H. and R. Luque. 2011. Advances on biomass pretreatment using ionic liquids: An overview. Energy Environ. Sci. 4: 3913-3929. https://doi.org/10.1039/c0ee00667j
  49. Turner, M. B., S. K. Spear, J. D. Holbrey, and R. D. Rogers. 2004. Production of bioactive cellulose films reconstituted from ionic liquids. Biomacromol. 5: 1379-1384. https://doi.org/10.1021/bm049748q
  50. Turner, M. B., S. K. Spear, J. D. Holbrey, D. T. Daly, and R. D. Rogers. 2005. Ionic liquid-reconstituted cellulose composites as solid support matrices for biocatalyst immobilization. Biomacromol. 6: 2497-2502. https://doi.org/10.1021/bm050199d
  51. van Rantwijk, F. and R. A. Sheldon. 2007. Biocatalysis in ionic liquids. Chem. Rev. 107: 2757-2785. https://doi.org/10.1021/cr050946x
  52. Viswanathan, G., S. Murugesan, V. Pushparaj, O. Nalamasu, P. M. Ajayan, and R. J. Linhardt. 2006. Preparation of biopolymer fibers by electrospinning from room temperature ionic liquids. Biomacromol. 7: 415-418. https://doi.org/10.1021/bm050837s
  53. Wang, Q., H. Tang, Q. Xie, L. Tan, Y. Zhang, B. Li, and S. Yao. 2007. Room-temperature ionicliquids/multi-walledcarbon nanotubes/ chitosan composite electrode for electrochemical analysis of NADH. Electrochimi. Acta. 52: 6630-6637. https://doi.org/10.1016/j.electacta.2007.04.057
  54. Wu, Y., T. Sasaki, S. Irie, and K. Sakurai. 2008. A novel biomass- ionic liquid platform for the utilization of native chitin. Polymer 49: 2321-2327. https://doi.org/10.1016/j.polymer.2008.03.027
  55. Xie, H. B., S. B. Zhang, and S. H. Li. 2006. Chitin and chitosan dissolved in ionic liquids as reversible sorbents of CO2. Green Chem. 8: 630-633. https://doi.org/10.1039/b517297g
  56. Yan, R., F. Zhao, J. Li, F. Xiao, S. Fan, and B. Zeng. 2007. Direct electrochemistry of horseradish peroxidase in gelatinhydrophobic ionic liquid gel films. Electrochimi. Acta. 52: 7425- 7431. https://doi.org/10.1016/j.electacta.2007.06.039
  57. Yang, Z. and W. Pan. 2005. Ionic liquids: Green solvents for nonaqueous biocatalysis. Enzym. Microb. Technol. 37: 19-28. https://doi.org/10.1016/j.enzmictec.2005.02.014
  58. Young, G., F. Nippgen, S. Titterbrandt, and M. J. Cooney. 2010. Lipid extraction from biomass using co-solvent mixtures of ionic liquids and polar covalent molecules. Sep. Purif. Technol. 72: 118-121. https://doi.org/10.1016/j.seppur.2010.01.009
  59. Zhao, H. 2006. Are ionic liquids kosmotropic or chaotropic? An evaluation of available thermodynamic parameters for quantifying the ion kosmotropicity of ionic liquids. J. Chem. Technol. Biotechnol. 81: 877-891. https://doi.org/10.1002/jctb.1449
  60. Zhao, H. 2010. Methods for stabilizing and activating enzymes in ionic liquids - a review. J. Chem. Technol. Biotechnol. 85: 891-907. https://doi.org/10.1002/jctb.2375
  61. Zhao, H. and S. V. Malhotra. 2002. Enzymatic resolution of amino acid esters using ionic liquid N-ethylpyridinium trifluoroacetate. Biotechnol. Lett. 24: 1257-1260. https://doi.org/10.1023/A:1016205924504
  62. Zhao, H., R. G. Luo, and S. V. Malhotra. 2003. Kinetic study on the enzymatic resolution of homophenylalanine ester using ionic liquids. Biotechnol. Prog. 19: 1016-1018. https://doi.org/10.1021/bp025721b
  63. Zhao, H., G. A. Baker, Z. Y. Song, O. Olubajo, T. Crittle, and D. Peter. 2008. Designing enzyme-compatible ionic liquids that can dissolve carbohydrates. Green Chem. 10: 696-705. https://doi.org/10.1039/b801489b
  64. Zhou, N., Y. Zhang, X. Gong, Q. Wang, and Y. Ma. 2012. Ionic liquids-based hydrolysis of Chlorella biomass for fermentable sugars. Bioresour. Technol. 118: 512-517. https://doi.org/10.1016/j.biortech.2012.05.074

Cited by

  1. 이온성 액체를 이용한 바이오매스 추출에 의해 얻어진 추출물의 건조 방법 vol.54, pp.3, 2013, https://doi.org/10.9713/kcer.2016.54.3.374