Free and immobilized Aspergillus niger epoxide hydrolase-catalyzed hydrolytic kinetic resolution of racemic p-chlorostyrene oxide in a neat organic solvent medium

Process Biochemistry

Volumn 45, Issue 2, 2010, Pages 210-216

  Karboune, Salwa ^a   Archelas, Alain ^b   Baratti, Jacques C ^b  

^a MCGILL UNIVERSITY   (Canada)

^b AIX MARSEILLE UNIVERSITY   (France)

Author keywords

Aspergillus niger; Epoxide hydrolase; Immobilization; Operational stability; Organic solvent; Resolution

Indexed keywords

ASPERGILLUS NIGER; DEAE CELLULOSE; ENANTIO; ENANTIOMERIC RATIO; EPOXIDE HYDROLASES; HYDROLYTIC KINETIC RESOLUTION; IMMOBILIZATION; NIGER; OPERATIONAL STABILITY; ORGANIC SOLVENT MEDIUM; P-CHLOROSTYRENE; PROTEIN IMMOBILIZATION; REACTION MEDIUM; REGIO-SELECTIVE; RELATIVE ACTIVITIES; REPEATED BATCH; SOLID FREE;

BATCH REACTORS; BINARY MIXTURES; ENZYME IMMOBILIZATION; ETHERS; HEPTANE; RECYCLING; STABILITY;

ORGANIC SOLVENTS;

ASPERGILLUS NIGER;

EID: 71249126477     PISSN: 13595113     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.procbio.2009.09.009     Document Type: Article

References (39)

1. Drauz K., and Waldmann H. Enzyme catalysis in organic synthesis (2002), Wiley-VCH, Weinheim
2. Schoemaker H.E., Mink D., and Wubbolts M.G. Dispelling the myths-biocatalysis in industrial synthesis. Science 299 (2003) 1694-1697
3. Archelas A., and Furstoss R. Synthetic application of epoxide hydrolases. Curr Opin Chem Biol 5 (2001) 112-119
4. de Vries E.J., and Janssen D.B. Biocatalytic conversion of epoxides. Curr Opin Biotechnol 14 (2003) 414-420
5. Choi W.J., and Choi Y.C. Production of chiral epoxides: epoxide hydrolase-catalyzed enantioselective hydrolysis. Biotechnol Bioproc Eng 10 (2005) 167-179
6. Bottalla A.-L., Ibrahim-Ouali M., Santelli M., Furstoss R., and Archelas A. Epoxide hydrolase-catalyzed kinetic resolution of a spiroepoxide, a key building block of various 11-heterosteroids. Adv Synth Catal 349 (2007) 1102-1110
7. Moussou P., Archelas A., Baratti J., and Furstoss R. Microbiological transformations. Part 39. Determination of the regioselectivity occurring during oxirane ring opening by epoxide hydrolases: a theoretical analysis and a new method for its determination. Tetrahedron Asymmetry 9 (1998) 1539-1547
8. Steinreiber A., Mayer S.F., and Faber K. Asymmetric total synthesis of a beer-aroma constituent based on enantioconvergent biocatalytic hydrolysis of trisubstituted epoxides. Synthesis 13 (2001) 2035-2039
9. Hwang S., Choi C.Y., and Lee E.Y. Enantioconvergent bioconversion of p-chlorostyrene oxide to (R)-p-chlorophenyl-1,2-ethandiol by the bacterial epoxide hydrolase of Caulobacter crescentus. Biotechnol Lett 30 (2008) 1219-1225
10. Lingyun R., Li C., Wilfred C., Kenneth F.R., and Thomas K.W. Protein engineering of epoxide hydrolase from Agrobacterium radiobacter AD1 for enhanced activity and enantioselective production of (R)-1-phenylethane-1,2-diol. Appl Environ Biotechnol 71 (2005) 3995-4003
11. Reetz M.T., Kahakeaw D., and Lohmer R. Addressing the numbers problem in directed evolution. Chem Bio Chem 9 (2008) 1797-1804
12. Reetz M.T., Wang L.-W., and Bocola M. Directed evolution of enantioselective enzymes: iterative cycles of CASTing for probing protein-sequence space. Angew Chem Int Ed Engl 45 (2006) 1236-1241
13. Monfort N., Archelas A., and Furstoss R. Enzymatic transformations. Part 55. Highly productive epoxide hydrolase catalysed resolution of an azole antifungal key synthon. Tetrahedron 60 (2004) 601-604
14. Doumèche D., Archelas A., and Furstoss R. Enzymatic transformations 62. Preparative scale synthesis of enantiopure glycidyl acetals using an Aspergillus niger epoxide hydrolase-catalysed kinetic resolution. Adv Synth Catal 348 (2006) 1948-1957
15. Deregnaucourt J., Archelas A., Barbirato F., Paris J.-P., and Furstoss R. Enzymatic transformations 63. High-concentration two liquid-liquid phase Aspergillus niger epoxide hydrolase-catalysed resolution: application to trifluoromethyl-substituted aromatic epoxides. Adv Synth Catal 349 (2007) 1405-1417
16. Karboune S., Archelas A., Furstoss R., and Baratti J. Immobilization of epoxide hydrolase from Aspergillus niger onto DEAE-cellulose: enzymatic properties and application for the enantioselective resolution of a racemic epoxide. J Mol Catal B: Enzym 32 (2005) 175-183
17. Mateo C., Archelas A., Fernandez-Lafuente R., Guisan J.-M., and Furstoss R. Enzymatic transformations. Immobilized A. niger epoxide hydrolase as a novel biocatalytic tool for repeated-batch hydrolytic kinetic resolution of epoxides. Org Biomol Chem 15 (2003) 2739-2743
18. Petri A., Marconcini P., and Salvadori P. Efficient immobilization of epoxide hydrolase onto silica gel and use in the enantioselective hydrolysis of racemic para-nitrostyrene oxide. J Mol Catal B: Enzym 32 (2004) 219-224
19. Halling P.J. Enzymatic conversions in organic and other low-water media. In: Drauz K., and Waldmann H. (Eds). Enzyme catalysis in organic synthesis. A comprehensive handbook. 2nd ed. vol. I (2002), Wiley-VCH/Verlag GmbH, Weinheim, Germany 259-286
20. Klibanov A.M. Improving enzymes by using them in organic solvents. Nature 409 (2001) 241-246
21. Carrea G., and Riva S. Properties and synthetic applications of enzymes in organic solvents. Angew Chem Int Ed 39 (2000) 2226-2254
22. Karboune S., Archelas A., and Baratti J. Properties of epoxide hydrolase from Aspergillus niger for the hydrolytic kinetic resolution of epoxides in pure organic media. Enz Microbiol Technol 39 (2006) 318-324
23. Arand M., Hemmer H., Durk H., Baratti J., Archelas A., Furstoss R., et al. Cloning and molecular characterization of a soluble epoxide hydrolase from Aspergillus niger that is related to mammalian microsomal epoxide hydrolase. Biochem J 344 (1999) 273-280
24. Naundorf A., Melzer G., Archelas A., Furstoss R., and Wohlgemuth R. Influence of pH on the expression of a recombinant epoxide hydrolase in Aspergillus niger. Biotechnol J 4 (2009) 756-765
25. Chen C.S., Fujimoto Y., Girdaukas G., and Sih C.J. Quantitative analyses of biochemical kinetic resolutions of enantiomers. J Am Chem Soc 104 (1982) 7294-7299
26. Holmquist M., Martinelle M., Berglund P., Clausen I.G., Patkar S., Svendsen A., et al. Lipases from Rhizomucor miehei and Humicola lanuginosa: modification of the lid covering the active site alters enantioselectivity. J Protein Chem 12 (1993) 747-755
27. Toscano G., Pirozzi D., Maremonti M., and Greco G. Solid-state enzyme deactivation in air and in organic solvents. Biotechnol Bioeng 44 (1994) 682-689
28. Xiu G.-H., Jiang L., and Li P. Mass-transfer limitations for immobilized enzyme-catalyzed kinetic resolution of racemate in a fixed-bed reactor. Biotechnol Bioeng 74 (2000) 30-39
29. Jongejan J.A., and Heijnen J.J. Diffusion limitation causes decreased enantioselectivity of esterification of 2-butanol by immobilized Candida Antarctica Lipase B. Biocatal Biotrans 19 (2000) 1-19
30. Mateo C., Fernandez-Lafuente R., Archelas A., Guisan J.M., and Furstoss R. Preparation of a very stable immobilized Solanum tuberosum epoxide hydrolase. Tetrahedron Asymmetry 18 (2007) 1233-1238
31. Basri M., Ampon K., Wan Yunus W.M.Z., Razak C.N.A., and Salleh A.B. Enzymatic synthesis of fatty esters by hydrophobic lipase derivatives immobilized on organic polymer beads. J Am Oil Chem Soc 72 (1995) 407-411
32. Pencreac'h G., and Baratti J. Activity of Burkholderia cepacia lipase in organic media is greatly enhanced after immobilisation on polypropylene support. Appl Microbiol Biotechnol 47 (1997) 630-635
33. van Tol J.B.A., Stevens R.M.M., Veldhuizen W.J., Jongejan J.A., and Duine J.A. Do organic solvents affect the catalytic properties of lipase? Intrinsic kinetic parameters of lipases in ester hydrolysis and formation in various organic solvents. Biotechnol Bioeng 47 (1995) 71-81
34. Ottolina G., Carrea G., Riva S., Sartore L., and Veronese F.M. Effect of the enzyme form on the activity, stability and enantioselectivity of lipoprotein lipase in toluene. Biotechnol Lett 14 (1992) 947-952
35. Fernandez-Lafuente R., Armisen P., Sabuquillo P., Fernandez-Lorente G., and Guisan J.M. Immobilization of lipases by selective adsorption on hydrophobic supports. Chem Phys Lipids 93 (1998) 185-197
36. Hartsough D.S., and Merz K.M. Protein dynamics and solvation in aqueous and nonaqueous environments. J Am Chem Soc 114 (1993) 6529-6537
37. Pencreac'h G., and Baratti J.C. Comparison of hydrolytic activity in water and heptane for thirty-two commercial lipase preparations. Enzyme Microb Technol 28 (2001) 473-479
38. Hazarika S., Goswami P., Dutta N.N., and Hazarika A.K. Ethyl oleate synthesis by porcine pancreatic lipase in organic solvents. Chem Eng J 85 (2002) 61-68
39. Ke T., Wescott R.C., and Klibanov M.A. Predictions of the solvent dependence of enzymatic prochiral selectivity by means of structure-based thermodynamic calculations. J Am Chem Soc 118 (1996) 3366-3374