Insight into microwave assisted immobilized Candida antarctica lipase B catalyzed kinetic resolution of RS-(±)-ketorolac

Process Biochemistry

Volumn 50, Issue 2, 2015, Pages 230-236

  Shinde, Somnath D ^a   Yadav, Ganapati D ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Enzyme catalysis; Esterification; Ketorolac; Kinetics; Microwave irradiation

Indexed keywords

CATALYSIS; ENANTIOMERS; ENZYME KINETICS; ENZYMES; ESTERIFICATION; ESTERS; IRRADIATION; KINETICS; MICROWAVES;

CANDIDA ANTARCTICA LIPASE B; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE ESTERIFICATION; ENZYME CATALYSIS; IMMOBILIZED ENZYME; KETOROLAC; KINETICS AND MECHANISM; PING-PONG BI-BI MECHANISM;

MICROWAVE IRRADIATION;

CANDIDA ANTARCTICA;

EID: 84922545294     PISSN: 13595113     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.procbio.2014.12.005     Document Type: Article

References (48)

1. G.D. Yadav, and I.V. Borkar Lipase-catalyzed hydrazinolysis of phenyl benzoate: kinetic modeling approach Process Biochem 45 2010 586 592
2. G.D. Yadav, and S. Devendran Lipase catalyzed synthesis of cinnamyl acetate via transesterification in non-aqueous medium Process Biochem 47 2012 496 502
3. J. Zhang, H. Shi, D. Wu, Z. Xing, A. Zhang, Y. Yang, et al. Recent developments in lipase-catalyzed synthesis of polymeric materials Process Biochem 2014 10.1016/j.procbio.2014.02.006 [in press]
4. Y. Yang, Y. Yu, Y. Zhang, C. Liu, W. Shi, and Q. Li Lipase/esterase-catalyzed ring-opening polymerization: a green polyester synthesis technique Process Biochem 46 2011 1900 1908
5. G. Tasnádi, C.K. Winkler, D. Clay, M. Hall, and K. Faber Reductive dehalogenation of β-haloacrylic ester derivatives mediated by ene-reductases Catal Sci Technol 2 2012 1548 1552
6. W.D. Fessner, D. Heyl, and M. Rale Multi-enzymatic cascade synthesis of d-fructose 6-phosphate and deoxy analogs as substrates for high-throughput aldolase screening Catal Sci Technol 2 2012 1596 1601
7. D. Yu, D. Ma, Z. Wang, Y. Wang, Y. Pan, and X. Fang Microwave-assisted enzymatic resolution of (RS)-2-octanol in ionic liquid Process Biochem 47 2012 479 484
8. D. Yu, P. Chen, L. Wang, Q. Gu, Y. Li, Z. Wang, et al. A chemo-enzymatic process for sequential kinetic resolution of (RS)-2-octanol under microwave irradiation Process Biochem 42 2007 1312 1318
9. D. Yu, H. Wu, A. Zhang, L. Tian, L. Liu, C. Wang, et al. Microwave irradiation-assisted isomerization of glucose to fructose by immobilized glucose isomerise Process Biochem 46 2011 599 603
10. D. Sebrão, M.M. Sá, and MdeG. Nascimento Regioselective acylation of d-ribono-1,4-lactone catalyzed by lipases Process Biochem 46 2011 551 556
11. Y. Han, J.T. Watson, G.D. Stucky, and A. Butler Catalytic activity of mesoporous silicate-immobilized chloroperoxidase J Mol Catal B: Enzym 17 2002 1 8
12. G.D. Yadav, and S.D. Shinde Kinetic modeling and optimization of immobilized Candida antarctica lipase B catalysed synthesis of butyl-4-methyl-3-oxopentanoate using response surface methodology Int J Chem React Eng 10 2012 A70
13. I. Rosen-Margalit, and J. Rishpon Novel approaches for the use of mediators in enzyme electrodes Biosens Bioelectron 8 1993 315 323
14. B. Kuswandi, R. Andres, and R. Narayanaswamy Optical fibre biosensors based on immobilised enzymes Analyst 126 2001 1469 1491
15. G. Dhawan, G. Sumana, and B.D. Malhotra Recent developments in urea biosensors Biochem Eng J 44 2009 42 52
16. G.D. Yadav, and S.D. Shinde Microwave irradiated immobilized lipase catalyzed synthesis of alkyl benzoate esters by transesterification: mechanism and kinetic modeling Ind Eng Chem Res 53 2014 8706 8713
17. G.D. Yadav, and S.R. Jadhav Synthesis of reusable lipases by immobilization on hexagonal mesoporous silica and encapsulation in calcium alginate: transesterification in non-aqueous medium Microporous Mesoporous Mater 86 2005 215 222
18. G.D. Yadav, A.D. Sajgure, and S.B. Dhoot Enzyme catalysis in fine chemical and pharmaceutical industries S.K. Bhattacharya, Enzyme mixtures and complex biosynthesis 2007 Landes Biosciences Austin, TX
19. R. Verger Interfacial activation of lipases: facts and artifacts Trends Biotechnol 15 1997 32 38
20. J. Gao, L. Shi, Y. Jiang, L. Zhou, and Y. He Formation of lipase Candida sp. 99-125 CLEAs in mesoporous silica: characterization and catalytic properties Catal Sci Technol 3 2013 3353 3359
21. C.G. Acevedo-Rocha, and M.T. Reetz Tuning lipase activity with perfluoro carboxylic acids as additives Catal Sci Technol 2 2012 1553 1555
22. M. Marciello, M. Filice, and J.M. Palomo Different strategies to enhance the activity of lipase catalysts Catal Sci Technol 2 2012 1531 1543
23. S. Talekar, V. Shah, S. Patil, and M. Nimbalkar Porous cross linked enzyme aggregates (p-CLEAs) of Saccharomyces cerevisiae invertase Catal Sci Technol 2 2012 1575 1579
24. G.D. Yadav, and J.B. Sontakke Optimization of chiral resolution of (+/-)-1-phenylethanol by statistical methods Intern J Chem React Eng 9 1 2011
25. D. Yu, C. Wang, Y. Yin, A. Zhang, G. Gao, and X. Fang A synergistic effect of microwave irradiation and ionic liquids on enzyme-catalyzed biodiesel production Green Chem 13 2011 1869 1875
26. J. Gising, L.R. Odell, and M. Larhed Microwave-assisted synthesis of small molecules targeting the infectious diseases tuberculosis, HIV/AIDS, malaria and hepatitis C Org Biomol Chem 10 2012 2713 2729
27. G.D. Yadav, and S. Devendran Lipase catalyzed kinetic resolution of (±)-1-(1-naphthyl) ethanol under microwave irradiation J Mol Catal B: Enzym 81 2012 58 65
28. Y. Shen, W. Guo, L. Qi, J. Qiao, F. Wang, and L. Mao Immobilization of trypsin via reactive polymer grafting from magnetic nanoparticles for microwave-assisted digestion J Mater Chem B 1 2013 2260 2267
29. P. Appukkuttan, V.P. Mehta, and E.V. Van der Eycken Microwave-assisted cycloaddition reactions Chem Soc Rev 39 2010 1467 1477
30. G.D. Yadav, and S. Devendran Microwave assisted enzyme catalysis: practice and perspective M.A.Z. Coelho, B.D. Ribeiro, Green chemistry and white biotechnology 2014 RSC Cambridge
31. G.D. Yadav, and S.D. Shinde Synergism of microwave irradiation and immobilized lipase catalysis in synthesis of 4,8-dimethylnon-7-en-1yl (2E)-3-phenylpro-2-enolate Int Rev Chem Eng 4 2012 589 596
32. G.D. Yadav, and S.D. Shinde Process intensification of immobilized lipase catalysis by microwave irradiation in the synthesis of 4-chloro-2-methylphenoxyacetic acid (MCPA) esters Biochem Eng J 90 2014 96 102
33. H. Horchani, M. Chaâbouni, Y. Gargouri, and A. Sayari Solvent-free lipase-catalyzed synthesis of long-chain starch esters using microwave heating: optimization by response surface methodology Carbohydr Polym 79 2010 466 474
34. L.M.C. Matos, I.C.R. Leal, and R.O.M.A. de Souza Diacylglycerol synthesis by lipase-catalyzed partial hydrolysis of palm oil under microwave irradiation and continuous flow conditions J Mol Catal B: Enzym 72 2011 36 39
35. G.D. Yadav, and P.A. Thorat Microwave assisted lipase catalyzed synthesis of isoamyl myristate in solvent-free system J Mol Catal B: Enzym 83 2012 16 22
36. P. Bachu, J.S. Gibson, J. Sperry, and M.A. Brimble The influence of microwave irradiation on lipase catalyzed kinetic resolution of racemic secondary alcohols Tetrahedron Asymmetry 18 2007 1618 1624
37. O.C. Kappe, B. Pieber, and D. Dallinger Microwave effects in organic synthesis: myth or reality? Angew Chem Int Ed 52 2013 1088 1094
38. J.M. Collins, and N.E. Leadbeater Microwave energy: a versatile tool for bioscience Org Biomol Chem 5 2007 1141 1150
39. D.D. Young, J. Nichols, R.M. Kelly, and A. Deiters Microwave activation of enzymatic catalysis J Am Chem Soc 130 2008 10048 10049
40. B. Rejasse, T. Besson, M.D. Legoy, and S. Lamare Influence of microwave irradiation on free Candida antartica lipase B activity and stability Org Biomol Chem 4 2006 3703 3707
41. J. Guo, Y. Zhuang, L. Chen, J. Liu, D. Li, and N. Ye Process optimization for microwave-assisted direct liquefaction of Sargassum polycystum c. agardh using response surface methodology Bioresour Technol 120 2012 19 25
42. Y.H. Kim, C.S. Cheong, S.H. Lee, and K.S. Kim Enzymatic kinetic resolution of ketorolac Tetrahedron Asymmetry 12 2001 1865 1869
43. B.Y. Kim, H.J. Doh, T.N. Le, W.J. Cho, C.S. Yong, H.G. Choi, et al. Ketorolac amide prodrugs for transdermal delivery: stability and in vitro rat skin permeation studies Int J Pharm 293 2005 193 202
44. D.R. Brocks, and F. Jamali Clinical pharmacokinetics of ketorolac tromethamine Clin Pharmacokinet 23 1992 415 427
45. G. Fulling, and C.J. Sih Enzymatic second-order asymmetric hydrolysis of ketorolac esters: in situ racemization J Am Chem Soc 109 1987 2846 2848
46. A. Palomer, M. Cabrg, J. Ginesta, D. Mauleon, and G. Carganico Resolution of rac-ketoprofen esters by enzymatic reactions in organic media Chirality 5 1993 320 328
47. G. Kraai, J.G.M. Winkelman, J.G. de Vries, and H.J. Heeres Kinetic studies on the Rhizomucor miehei lipase catalyzed esterification reaction of oleic acid with 1-butanol in a biphasic system Biochem Eng J 41 2008 87 94
48. I.H. Segel Enzyme kinetics: behavior and analysis of rapid equilibrium and steadystate enzyme systems 1975 Wiley Interscience New York