Improving activity and enantioselectivity of lipase via immobilization on macroporous resin for resolution of racemic 1- phenylethanol in non-aqueous medium

BMC Biotechnology

Volumn 13, Issue , 2013, Pages

  Li, Xiang ^a   Huang, Shuangshuang ^a   Xu, Li ^a   Yan, Yunjun ^a  

^a HUAZHONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ADSORPTION DESORPTION; BURKHOLDERIA CEPACIA; CATALYTIC EFFICIENCIES; CATALYTIC PERFORMANCE; ENERGY DISPERSIVE SPECTROSCOPIES (EDS); ENZYMATIC BIOTRANSFORMATION; LIPASE IMMOBILIZATION; SECONDARY STRUCTURES;

ENANTIOSELECTIVITY; ENERGY DISPERSIVE SPECTROSCOPY; ETHANOL; INDUSTRIAL APPLICATIONS; INFRARED SPECTROSCOPY; RESINS; REUSABILITY; SCANNING ELECTRON MICROSCOPY;

LIPASES;

1 PHENYLETHANOL; BACTERIAL ENZYME; BURKHOLDERIA CEPACIA LIPASE; IMMOBILIZED ENZYME; MACROPOROUS RESIN; RESIN; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG; VINYL ACETATE;

AQUEOUS SOLUTION; ARTICLE; BURKHOLDERIA CEPACIA; CATALYSIS; CONTROLLED STUDY; ENANTIOSELECTIVITY; ENZYME ACTIVITY; INFRARED SPECTROSCOPY; NON AQUEOUS MEDIUM; NONHUMAN; PARTICLE SIZE; POROSITY; PROTEIN SECONDARY STRUCTURE; REACTION TIME; SCANNING ELECTRON MICROSCOPY; TEMPERATURE; THERMOSTABILITY; WATER CONTENT;

BURKHOLDERIA CEPACIA;

ADSORPTION; BENZYL ALCOHOLS; BURKHOLDERIA CEPACIA; ENZYMES, IMMOBILIZED; LIPASE; MICROSCOPY, ELECTRON, SCANNING; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; TEMPERATURE; VINYL COMPOUNDS;

EID: 84886421190     PISSN: None     EISSN: 14726750     Source Type: Journal    
DOI: 10.1186/1472-6750-13-92     Document Type: Article

References (35)

1. Sellami M, Aissa I, Frikha F, Gargouri Y, Miled N. Immobilized Rhizopus oryzae lipase catalyzed synthesis of palm stearin and cetyl alcohol wax esters: Optimization by response surface methodology. BMC Biotechnol 2011, 11(1):68. 10.1186/1472-6750-11-68, 3145570, 21682865.
2. Alissandratos A, Baudendistel N, Flitsch S, Hauer B, Halling P. Lipase-catalysed acylation of starch and determination of the degree of substitution by methanolysis and GC. BMC Biotechnol 2010, 10(1):82. 10.1186/1472-6750-10-82, 3006361, 21114817.
3. Wang H, Sun H, Wei D. Discovery and characterization of a highly efficient enantioselective mandelonitrile hydrolase from Burkholderia cenocepacia J2315 by phylogeny-based enzymatic substrate specificity prediction. BMC Biotechnol 2013, 13(1):14. 10.1186/1472-6750-13-14, 3599355, 23414071.
4. Liu Y, Chen D, Yan Y, Peng C, Xu L. Biodiesel synthesis and conformation of lipase from Burkholderia cepacia in room temperature ionic liquids and organic solvents. Bioresource Technol 2011, 102(22):10414-10418.
5. Liu T, Liu Y, Wang X, Li Q, Wang J, Yan Y. Improving catalytic performance of Burkholderia cepacia lipase immobilized on macroporous resin NKA. J Mol Catal B: Enzym 2011, 71(1-2):45-50.
6. Herbst D, Peper S, Niemeyer B. Enzyme catalysis in organic solvents: influence of water content, solvent composition and temperature on Candida rugosa lipase catalyzed transesterification. J Biotechnol 2012, 162(4):398-403. 10.1016/j.jbiotec.2012.03.011, 22465292.
7. Klibanov AM. Why are enzymes less active in organic solvents than in water?. Trends Biotechnol 1997, 15(3):97-101. 10.1016/S0167-7799(97)01013-5, 9080715.
8. Garcia-Galan C, Berenguer-Murcia T, Fernandez-Lafuente R, Rodrigues RC. Potential of different enzyme immobilization strategies to improve enzyme performance. Adv Synth Catal 2011, 353(16):2885-2904.
9. Cao L. Immobilised enzymes: science or art?. Curr Opin Chem Biol 2005, 9(2):217-226. 10.1016/j.cbpa.2005.02.014, 15811808.
10. Alloue W, Destain J, Medjoub T, Ghalfi H, Kabran P, Thonart P. Comparison of Yarrowia lipolytica lipase immobilization yield of entrapment, adsorption, and covalent bond techniques. Appl Biochem Biotechnol 2008, 150(1):51-63. 10.1007/s12010-008-8148-9, 18327546.
11. Yan Y, Zhang X, Chen D. Enhanced catalysis of Yarrowia lipolytica lipase LIP2 immobilized on macroporous resin and its application in enrichment of polyunsaturated fatty acids. Bioresource Technol 2013, 131:179-187.
12. Gao Y, Tan T, Nie K, Wang F. Immobilization of lipase on macroporous resin and its application in synthesis of biodiesel in low aqueous media. Chin J Biotechnol 2006, 22(1):114-118.
13. Gao S, Wang Y, Diao X, Luo G, Dai Y. Effect of pore diameter and cross-linking method on the immobilization efficiency of Candida rugosa lipase in SBA-15. Bioresource Technol 2010, 101(11):3830-3837.
14. Kharrat N, Ali YB, Marzouk S, Gargouri Y, Karra-Châabouni M. Immobilization of Rhizopus oryzae lipase on silica aerogels by adsorption: Comparison with the free enzyme. Process Biochem 2011, 46(5):1083-1089.
15. Dib I, Nidetzky B. The stabilizing effects of immobilization in D-amino acid oxidase from Trigonopsis variabilis. BMC Biotechnol 2008, 8(1):72. 10.1186/1472-6750-8-72, 2557008, 18798979.
16. Shah S, Gupta MN. Kinetic resolution of (±)-1-phenylethanol in [Bmim][PF6] using high activity preparations of lipases. Bioorg Med Chem Lett 2007, 17(4):921-924. 10.1016/j.bmcl.2006.11.057, 17157018.
17. Ghanem A, Aboul-Enein HY. Application of lipases in kinetic resolution of racemates. Chirality 2005, 17(1):1-15. 10.1002/chir.20089, 15515046.
18. Chua LS, Sarmidi MR. Immobilised lipase-catalysed resolution of (R, S)-1-phenylethanol in recirculated packed bed reactor. J Mol Catal B: Enzym 2004, 28(2-3):111-119.
19. Ghamgui H, Karra-Chaâbouni M, Bezzine S, Miled N, Gargouri Y. Production of isoamyl acetate with immobilized Staphylococcus simulans lipase in a solvent-free system. Enzyme Microb Tech 2006, 38(6):788-794.
20. Persson M, Costes D, Wehtje E, Adlercreutz P. Effects of solvent, water activity and temperature on lipase and hydroxynitrile lyase enantioselectivity. Enzyme Microb Tech 2002, 30(7):916-923.
21. Xia X, Wang C, Yang B, Wang Y, Wang X. Water activity dependence of lipases in non-aqueous biocatalysis. Appl Biochem Biotech 2009, 159(3):759-767.
22. Phillips RS. Temperature modulation of the stereochemistry of enzymatic catalysis: Prospects for exploitation. Trends Biotechnol 1996, 14(1):13-16.
23. Blanco RM, Terreros P, Muñoz N, Serra E. Ethanol improves lipase immobilization on a hydrophobic support. J Mol Catal B: Enzym 2007, 47(1-2):13-20.
24. Gao S, Wang Y, Wang W, Luo G, Dai Y. Enhancing performance of lipase immobilized on methyl-modified silica aerogels at the adsorption and catalysis processes: Effect of cosolvents. J Mol Catal B: Enzym 2010, 62(3-4):218-224.
25. Ema T. Rational strategies for highly enantioselective lipase-catalyzed kinetic resolutions of very bulky chiral compounds: substrate design and high-temperature biocatalysis. Tetrahedron: Asymmetry 2004, 15(18):2765-2770.
26. Schrag JD, Li Y, Cygler M, Lang D, Burgdorf T, Hecht H, Schmid R, Schomburg D, Rydel TJ, Oliver JD, et al. The open conformation of a Pseudomonas lipase. Structure 1997, 5(2):187-202. 10.1016/S0969-2126(97)00178-0, 9032074.
27. Wang X, Zhou G, Zhang H, Du S, Xu Y, Wang C. Immobilization and catalytic activity of lipase on mesoporous silica prepared from biocompatible gelatin organic template. J Non-Cryst Solids 2011, 357(15):3027-3032.
28. Chen B, Miller EM, Miller L, Maikner JJ, Gross RA. Effects of macroporous resin size on Candida antarctica lipase B adsorption, fraction of active molecules, and catalytic activity for polyester synthesis. Langmuir 2006, 23(3):1381-1387.
29. Pribic R, Vanstokkum IHM, Chapman D, Haris PI, Bloemendal M. Protein secondary structure from Fourier transform infrared and/or circular dichroism spectra. Anal Biochem 1993, 214(2):366-378. 10.1006/abio.1993.1511, 8109723.
30. Haris PI, Severcan F. FTIR spectroscopic characterization of protein structure in aqueous and non-aqueous media. J Mol Catal B: Enzym 1999, 7(1-4):207-221.
31. Foresti ML, Alimenti GA, Ferreira ML. Interfacial activation and bioimprinting of Candida rugosa lipase immobilized on polypropylene: effect on the enzymatic activity in solvent-free ethyl oleate synthesis. Enzyme Microb Tech 2005, 36(2-3):338-349.
32. Wang J, Ma C, Bao Y, Xu P. Lipase entrapment in protamine-induced bio-zirconia particles: Characterization and application to the resolution of (R, S)-1-phenylethanol. Enzyme Microb Tech 2012, 51(1):40-46.
33. Bradford MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 1976, 72(1-2):248-254.
34. Chen CS, Fujimoto Y, Girdaukas G, Sih CJ. Quantitative analyses of biochemical kinetic resolutions of enantiomers. J Am Chem Soc 1982, 104:7294-7299.
35. Yang C, Wang F, Lan D, Whiteley C, Yang B, Wang Y. Effects of organic solvents on activity and conformation of recombinant Candida antarctica lipase A produced by Pichia pastoris. Process Biochem 2012, 47(3):533-537.