Protein-Coated Microcrystals from Candida rugosa Lipase: Its Immobilization, Characterization, and Application in Resolution of Racemic Ibuprofen

Applied Biochemistry and Biotechnology

Volumn 177, Issue 1, 2015, Pages 36-47

  Huang, Shuangshuang ^a   Li, Xiang ^a   Xu, Li ^a   Ke, Caixia ^a   Zhang, Rui ^a   Yan, Yunjun ^a  

^a HUAZHONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Enantioselective esterification Ibuprofen; Lipase; Protein coated micro crystals (PCMCs)

Indexed keywords

CANDIDA; DRUG PRODUCTS; ENANTIOMERS; ENZYME ACTIVITY; ENZYMES; ESTERIFICATION; ESTERS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; MICROCRYSTALS; PROTEINS; YEAST;

ACTIVITY ENHANCEMENT; CANDIDA RUGOSA LIPASE; ENANTIOSELECTIVE ESTERIFICATION; IBUPROFEN ENANTIOMERS; OPERATIONAL STABILITY; ORGANIC SOLVENT TOLERANCE; PROTEIN COATED MICRO-CRYSTALS; PROTEINCOATED MICRO-CRYSTALS (PCMCS);

LIPASES;

IBUPROFEN; OCTANOL; TRIACYLGLYCEROL LIPASE; IMMOBILIZED ENZYME;

ARTICLE; BIOCATALYST; CANDIDA RUGOSA; CATALYSIS; CATALYTIC EFFICIENCY; CONFORMATION; CONTROLLED STUDY; CRYSTAL; ENANTIOMER; ENZYME ACTIVITY; ENZYME ANALYSIS; ENZYME IMMOBILIZATION; ESTERIFICATION; INFRARED SPECTROSCOPY; PH; PROTEIN SECONDARY STRUCTURE; SCANNING ELECTRON MICROSCOPY; THERMOSTABILITY; CANDIDA; CHEMISTRY; CRYSTALLIZATION; ENZYME STABILITY; ENZYMOLOGY; STEREOISOMERISM; ULTRASTRUCTURE;

CANDIDA RUGOSA;

CANDIDA; CRYSTALLIZATION; ENZYME STABILITY; ENZYMES, IMMOBILIZED; IBUPROFEN; LIPASE; PROTEIN STRUCTURE, SECONDARY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STEREOISOMERISM;

EID: 84940450243     PISSN: 02732289     EISSN: 15590291     Source Type: Journal    
DOI: 10.1007/s12010-015-1725-9     Document Type: Article

References (39)

1. Schmid, R. D., & Verger, R. (1998). Lipases: interfacial enzymes with attractive applications. Angewandte Chemie International Edition, 37(12), 1608–1633.
2. Singh, A. K., & Mukhopadhyay, M. (2012). Overview of fungal lipase: a review. Applied Biochemistry and Biotechnology, 166(2), 486–520.
3. Xie, Y. C., Liu, H. Z., & Chen, J. Y. (1998). Candida rugosa lipase catalyzed esterification of racemic ibuprofen with butanol: racemization of R-ibuprofen and chemical hydrolysis of S-ester formed. Biotechnology Letters, 20(5), 455–458.
4. Contesini, F. J., & de Oliveira Carvalho, P. (2006). Esterification of (RS)-Ibuprofen by native and commercial lipases in a two-phase system containing ionic liquids. Tetrahedron: Asymmetry, 17(14), 2069–2073.
5. Santos, J. C., Mijone, P. D., Nunes, G. F., Perez, V. H., & de Castro, H. F. (2008). Covalent attachment of Candida rugosa lipase on chemically modified hybrid matrix of polysiloxane-polyvinyl alcohol with different activating compounds. Colloids and surfaces B, Biointerfaces, 61(2), 229–236.
6. Adlercreutz, P. (2013). Immobilisation and application of lipases in organic media. Chemical Society Reviews, 42(15), 6406–6436.
7. Kreiner, M., Parker, M. C., & Moore, B. D. (2001). Enzyme-coated micro-crystals: a 1-step method for high activity biocatalyst preparation. Chemical Communications, 12, 1096–1097.
8. Shah, S., Sharma, A., & Gupta, M. N. (2008). Cross-linked protein-coated microcrystals as biocatalysts in non-aqueous solvents. Biocatalysis and Biotransformation, 26(4), 266–271.
9. Kumari, V., Shah, S., & Gupta, M. N. (2007). Preparation of biodiesel by lipase- catalyzed transesterification of high free fatty acid containing oil from Madhuca indica. Energy & Fuels, 21(1), 368–372.
10. Shah, S., & Gupta, M. N. (2007). Kinetic resolution of (+/−)-1-phenylethanol in [Bmim][PF6] using high activity preparations of lipases. Bioorganic & Medicinal Chemistry Letters, 17(4), 921–924.
11. Kreiner, M., Amorim Fernandes, J. F., O’Farrell, N., Halling, P. J., & Parker, M. C. (2005). Stability of protein-coated microcrystals in organic solvents. Journal of Molecular Catalysis B: Enzymatic, 33(3-6), 65–72.
12. Berglund, P. (2001). Controlling lipase enantioselectivity for organic synthesis. Biomolecular Engineering, 18(1), 13–22.
13. Dominguez de Maria, P., Sanchez-Montero, J. M., Sinisterra, J. V., & Alcantara, A. R. (2006). Understanding Candida rugosa lipases: an overview. Biotechnology Advances, 24(2), 180–196.
14. Li, X., Huang, S., Xu, L., & Yan, Y. (2013). Conformation and catalytic properties studies of Candida rugosa Lip7 via enantioselective esterification of Ibuprofen in organic solvents and ionic liquids. The Scientific World Journal, 2013, 1–7.
15. Colton, I. J., Ahmed, S. N., & Kazlauskas, R. J. (1995). A 2-propanol treatment increases the enantioselectivity of Candida rugosa lipase toward esters of chiral carboxylic acids. The Journal of Organic Chemistry, 60(1), 212–217.
16. Yang, Z., Niu, X., Fang, X., Chen, G., Zhang, H., Yue, H., Wang, L., Zhao, D., & Wang, Z. (2013). Enantioselective esterification of Ibuprofen under microwave irradiation. Molecules, 18(5), 5472–5481.
17. Tutar, H., Yilmaz, E., Pehlivan, E., & Yilmaz, M. (2009). Immobilization of Candida rugosa lipase on sporopollenin from Lycopodium clavatum. International Journal of Biological Macromolecules, 45(3), 315–320.
18. Yu, H., Wu, J., & Ching, C. B. (2004). Enhanced activity and enantioselectivity ofCandida rugosa lipase immobilized on macroporous adsorptive resins for ibuprofen resolution. Biotechnology Letters, 26(8), 629–633.
19. Hart, F. D., & Huskisson, E. (1984). Non-steroidal anti-inflammatory drugs. Current status and rational therapeutic use. Drugs, 27(3), 232–255.
20. Liu, Y., Wang, F., & Tan, T. (2009). Effects of alcohol and solvent on the performance of lipase from Candida sp. in enantioselective esterification of racemic ibuprofen. Journal of Molecular Catalysis B: Enzymatic, 56(2), 126–130.
21. Chen, J. C., & Tsai, S. W. (2000). Enantioselective synthesis of (S)Ibuprofen ester prodrug in cyclohexane by Candida rugosa lipase immobilized on accurel MP1000. Biotechnology Progress, 16(6), 986–992.
22. Bradford, M. M. (1976). A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Analytical Biochemistry, 72(1), 248–254.
23. Yang, C., Wang, F., Lan, D., Whiteley, C., Yang, B., & Wang, Y. (2012). Effects of organic solvents on activity and conformation of recombinant Candida antarctica lipase A produced by Pichia pastoris. Process Biochemistry, 47(3), 533–537.
24. Raita, M., Champreda, V., & Laosiripojana, N. (2010). Biocatalytic ethanolysis of palm oil for biodiesel production using microcrystalline lipase in tert-butanol system. Process Biochemistry, 45(6), 829–834.
25. Costantino, H. R., Griebenow, K., Langer, R., & Klibanov, A. M. (1997). On the pH memory of lyophilized compounds containing protein functional groups. Biotechnology and Bioengineering, 53(3), 345–348.
26. Yu, H. W., Chen, H., Wang, X., Yang, Y. Y., & Ching, C. B. (2006). Cross-linked enzyme aggregates (CLEAs) with controlled particles: application to Candida rugosa lipase. Journal of Molecular Catalysis B: Enzymatic, 43(1-4), 124–127.
27. Yu, W. H., Fang, M., Tong, D. S., Shao, P., Xu, T. N., & Zhou, C. H. (2013). Immobilization of Candida rugosa lipase on hexagonal mesoporous silicas and selective esterification in nonaqueous medium. Biochemical Engineering Journal, 70, 97–105.
28. Raita, M., Laothanachareon, T., Champreda, V., & Laosiripojana, N. (2011). Biocatalytic esterification of palm oil fatty acids for biodiesel production using glycine-based cross-linked protein coated microcrystalline lipase. Journal of Molecular Catalysis B: Enzymatic, 73(1-4), 74–79.
29. Kreiner, M., & Parker, M. C. (2005). Protein-coated microcrystals for use in organic solvents: application to oxidoreductases. Biotechnology Letters, 27(20), 1571–1577.
30. Moore, B. D., Partridge, J., Bradley, L. & Vos, J. (2008). Precipitation stabilising compositions. A61K 9/14 (2006.01).
31. 4 micro-crystals: preparation, characterization, and application in biodiesel production using various oil feedstocks. Bioresource Technology, 110, 224–231.
32. Zhu, K., Jutila, A., Tuominen, E. K., Patkar, S. A., Svendsen, A., & Kinnunen, P. K. (2001). Impact of the tryptophan residues of Humicola lanuginosa lipase on its thermal stability. Biochimica et Biophysica Acta (BBA)-Protein Structure and Molecular Enzymology, 1547(2), 329–338.
33. Bai, S., Guo, Z., Liu, W., & Sun, Y. (2006). Resolution of (±)-menthol by immobilized Candida rugosa lipaseon superparamagnetic nanoparticles. Food Chemistry, 96(1), 1–7.
34. Chen, D., Peng, C., Zhang, H., & Yan, Y. (2013). Assessment of activities and conformation of lipases treated with sub- and supercritical carbon dioxide. Applied Biochemistry and Biotechnology, 169(7), 2189–2201.
35. 2 pretreatment on the conformation and catalytic properties of Candida rugosa lipase. Journal of Molecular Catalysis B: Enzymatic, 90, 123–127.
36. Pavlidis, I. V., Gournis, D., Papadopoulos, G. K., & Stamatis, H. (2009). Lipases in water-in-ionic liquid microemulsions: structural and activity studies. Journal of Molecular Catalysis B: Enzymatic, 60(1-2), 50–56.
37. Sheldon, R. A., Lau, R. M., Sorgedrager, M. J., van Rantwijk, F., & Seddon, K. R. (2002). Biocatalysis in ionic liquids. Green Chemistry, 4(2), 147–151.
38. Solanki, K., Gupta, M. N., & Halling, P. J. (2012). Examining structure-activity correlations of some high activity enzyme preparations for low water media. Bioresource Technology, 115, 147–151.
39. Gaur, R., Gupta, G. N., Vamsikrishnan, M., & Khare, S. K. (2008). Protein-coated microcrystals of Pseudomonas aeruginosa PseA lipase. Applied Biochemistry and Biotechnology, 151(2-3), 160–166.