Skip to main content
Log in

Enzymatic reaction of ethanol and oleic acid by lipase and lignin peroxidase in rhamnolipid (RL) reversed micelles

  • Published:
Journal of Central South University Aims and scope Submit manuscript

Abstract

An environment friendly bio-surfactant of rhamnolipid (RL) was used as a solvent. The enzymatic reaction of oleic acid catalyzed by lipase and lignin peroxidase (lip) was evaluated. The optimum conditions of enzymatic reaction catalyzed by lipase (lip) were water to amphiphile molar ratio of 30 (20), RL of 60 (60) critical micelle concentration (CMC), pH of 7.0 (3.0) and temperature of 40 (30) °C, respectively. The change of enzyme conformation indicates that, for catalytic of lipase, water content is the most important factor of the enzymatic reaction of oleic acid, and pH for lip. With individual optimum conditions, the enzymatic efficiency of oleic acid catalyzed by lipase is higher than that by lip. In the presence of ethanol, the enzymatic reaction of oleic acid catalyzed by lipase suits Ping-Pong Bi-Bi mechanism. As an alternative to chemical reversed micelles, the RL reversed micelles are promising methods to enzymatic reaction of oleic acid.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. PENG Xing, YUAN Xing-zhong, ZENG Guang-ming. Extraction and purification of laccase by employing a novel rhamnolipid reversed micellar system [J]. Process Biochemistry, 2012, 47(5):742–748.

    Article  Google Scholar 

  2. RITER UNDIKS E P, KIMMEL L. Form amide in reverse micelles: restricted environment effects on molecular motion [J]. Phys Chem B, 1998, 102: 7931–7938.

    Article  Google Scholar 

  3. MUHAMMAD M, YOSHISHIGE H. Effect of aprotic solvents on the enzymatic activity of lipase in AOT reversed micelles [J]. Biochemical Engineering Journal, 2006, 30(3): 237–244.

    Article  Google Scholar 

  4. CRISTINA C, JOAQUIM C. Reverse micelles as reaction media for lipases [J]. Biochimie, 2000, 82(11): 1063–1085.

    Article  Google Scholar 

  5. ENRICO B, MARIA F, OSVALDO L. Lignin peroxidase catalysed oxidation of 4-methoxymandelic acid — The role of mediator structure [J]. Tetrahedron, 2002, 58(40):8087–8093.

    Article  Google Scholar 

  6. ZHANG Yun, HUANG Feng, LI Yue-zhong. Catalytic performance of lignin peroxidase in a novel reverse micelle [J]. Colloids and Surfaces B: Biointerfaces, 2008, 65(1): 50–53.

    Article  Google Scholar 

  7. WANG Wei, WEN Xiang-hua. Expression of lignin peroxidase H2 from Phanerochaete chrysosporium by multi-copy recombinant Pichia strain [J]. Journal of Environmental Sciences, 2009, 21(2): 218–222.

    Article  Google Scholar 

  8. JUN M, OKAZAKI S Y. Catalytic properties of lignin peroxidase ALiP-P3 hosted in reversed micelles [J]. Biochemical Engineering Journal, 2001, 8(2): 129–134.

    Article  Google Scholar 

  9. CHULALAKSANANUKUL W, CONDORE T J S, DELORME P, WILLEMOT R M. Kinetic study of esterification by immobilized lipase in n-hexane [J]. FEBS, 1990: 181–184.

    Google Scholar 

  10. OLIVEIRA A C, ROSA M F, AIRES-BARROS M R, CABRAL J M S. Enzymatic esterification of ethanol and oleic acid—A kinetic studies [J]. Journal of Molecular Catalysis B: Enzymatic, 2001, 11(4): 999–1005.

    Article  Google Scholar 

  11. ZHANG Wei-wei, NA Wang, ZHOU Yu-jie, TING He. Enhancement of activity and stability of lipase by microemulsion-based organogels (MBGs) immobilization and application for synthesis of arylethyl acetate [J]. Journal of Molecular Catalysis B: Enzymatic, 2012, 78: 65–71.

    Article  Google Scholar 

  12. XUE Lu-yan, ZOU Fei-xue, ZHAO Yin, HUANG Xi-rong, QU Yin-bo. Nitrile group as infrared probe for the characterization of the conformation of bovine serum albumin solubilized in reverse micelles [J]. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2012, 97: 858–863.

    Article  Google Scholar 

  13. CHEN Xiang-yan, YI Ru, CHEN Feng-liang. FTIR spectroscopic characterization of soy proteins obtained through AOT reverse micelles [J]. Food Hydrocolloids, 2013, 31(2): 435–437.

    Article  MathSciNet  Google Scholar 

  14. RAGHAVENDRA T, SAYANIA D, MADAMWAR D. Synthesis of the ‘green apple ester’ ethyl valerate in organic solvents by Candida rugosa lipase immobilized in MBGs in organic solvents: Effects of immobilization and reaction parameters [J]. Journal of Molecular Catalysis B: Enzymatic, 2010, 63(1): 31–38.

    Article  Google Scholar 

  15. ZHOU Guo-wei, LI Gan-zuo, XU Jian. Kinetic studies of lipase-catalyzed esterificationin water-in-oil microemulsions and the catalytic behavior of immobilized lipase in MBGs [J]. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2001, 194: 41–47.

    Article  Google Scholar 

  16. SECUNDO F, CARREA G. Lipase activity and conformation in neat organic solvents [J]. Journal of Molecular Catalysis B: Enzymatic, 2002, 19: 93–102.

    Article  Google Scholar 

  17. NAGAYAMA K, DOI T. Kinetic characterization of esterification catalyzed by Rhizopus delemar lipase in lecithin-AOT microemulsion systems [J]. Journal of Molecular Catalysis B: Enzymatic, 1998, 4(1): 25–32.

    Article  Google Scholar 

  18. KAZUMITSU N, TOMOMI O, MIKIO K. Esterification by Rhizopus delemar lipase in organic solvent using sugar ester reverse micelles [J]. Biochemical Engineering Journal, 2001, 9(1): 67–72.

    Article  Google Scholar 

  19. ZAMAN M M, HAYASHII Y, TALUKDER M M R, KAWANISHI T. Activity of acetone-treated Chromobacterium viscosum lipase in AOT reverse micelles in the presence of low molecular weight polyethylene glycol [J]. Biochemical Engineering Journal, 2006, 29(1): 46–54.

    Article  Google Scholar 

  20. WOLF R, LUISI P L. Micellar solubilization of proteins in aprotic solvents and their spectroscopic characterization [J]. Helv Chim Acta, 1979, 89(1): 740–753.

    Google Scholar 

  21. VELASCO F. Enzyme activation by denaturants in organic solvent systems with a low water content [J]. Eur J Biochem, 1992, 105: 509–518.

    Google Scholar 

  22. GADIN E, LION Y. Diffusion-concentration product of oxygen within water pools of Aerosol OT-heptane reverse micelles [J]. J Phys Chem, 1984, 88: 280–284.

    Article  Google Scholar 

  23. FERNANDES M L M, KRIEGER N, BARON A M, ZAMORA P P, RAMOS L P, MITCHELL D A. Hydrolysis and synthesis reactions catalysed by thermomyces lanuginosa lipase in the AOT/Isooctane reversed micellar system [J]. Journal of Molecular Catalysis B: Enzymatic, 2004, 30(1): 43–49.

    Article  Google Scholar 

  24. ELFANSO E, GARLAND M. In situ monitoring of turbid immobilized lipase-catalyzed esterification of oleic acid using fiber-optic Raman spectroscopy [J]. Catalysis Today, 2010, 155(3): 223–226.

    Article  Google Scholar 

  25. GARCIA T, COTERON A, MARTINEZ M, ARACIL J. Kinetic model for the esterification of oleic acid and cetyl alcohol using an immobilized lipase as catalyst [J]. Chemical Engineering Science, 2000, 55(8): 1411–1423.

    Article  Google Scholar 

  26. DEBNATH S, DAS D. Unsaturation at the surfactant head: Influence on the activity of lipase and horseradish peroxidase in reverse micelles [J]. Biochemical and Biophysical Research Communications, 2007, 356(1): 163–168.

    Article  Google Scholar 

  27. NAGAYAMA K, KARAIWA K. Esterification activity and stability of Candida rugosa lipase in AOT microemulsion-based organogels. [J] Biochemical Engineering Journal, 1998, 2(2): 121–126.

    Article  Google Scholar 

  28. TABOR R, EASTOE J, DOWDING P. A two-step model for surfactant adsorption at solid surfaces [J]. Journal of Colloid and Interface Science, 2010, 346(2): 424–428.

    Article  Google Scholar 

  29. SINGH D, CHANDER M, PARAMJIT G. Involvement of lignin peroxidase, manganese peroxidase and laccase in degradation and selective ligninolysis of wheat straw [J]. International Biodeterioration & Biodegradation, 2002, 50(2): 115–120.

    Article  Google Scholar 

  30. JUTILA A, ZHU K. Fluorescence spectroscopic characterization of Humicola lanuginose lipase dissolved in its substrate [J]. Biochimica et Biophysica Acta, 2004, 17:181–189.

    Article  Google Scholar 

  31. LAN Jing, HUANG Xi-rong. High efficient degradation of dyes with lignin peroxidase coupled with glucose oxidase[J]. Journal of Biotechnology, 2006, 123(4): 493–504.

    Article  Google Scholar 

  32. ZHANG Yu-fen, DOMINIC R. Activity, conformation and thermal stability of laccase and glucose oxidase in poly (ethyleneimine) microcapsules for immobilization in paper [J]. Process Biochemistry, 2011, 46: 993–1000.

    Article  Google Scholar 

  33. ANA S, MARIA R, MELO E. Thermal denaturation of HRPA2: pH-dependent conformational changes [J]. Enzyme and Microbial Technology, 2007, 40(4): 696–703.

    Article  Google Scholar 

  34. CARLOS T, OTERO C. Influence of the organic solvents on the activity in water and the conformation of Candida rugosa lipase: Description of a lipase-activating pretreatment [J]. Enzyme and Microbial Technology, 1996, 19(8): 594–600.

    Article  Google Scholar 

  35. HONG D P, LEE S S, KUBOI R. Conformational transition and mass transfer in extraction of proteins by AOT–alcohol–isooctane reverse micellar systems [J]. Journal of Chromatography B, 2000, 743(1): 203–213.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Xing-zhong Yuan  (袁兴中).

Additional information

Foundation item: Projects(50978087, 51009063, 50978088) supported by the National Natural Science Foundation of China

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bao, S., Yuan, Xz., Peng, X. et al. Enzymatic reaction of ethanol and oleic acid by lipase and lignin peroxidase in rhamnolipid (RL) reversed micelles. J. Cent. South Univ. 22, 2936–2944 (2015). https://doi.org/10.1007/s11771-015-2829-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11771-015-2829-7

Keywords

Navigation