A two-step enzymatic resolution of glycidyl butyrate

Process Biochemistry

Volumn 42, Issue 9, 2007, Pages 1319-1325

  Yu, Dahai ^a   Wang, Lei ^a   Gu, Qiang ^a   Chen, Peng ^a   Li, Yan ^a   Wang, Zhi ^a   Cao, Shugui ^a  

^a JILIN UNIVERSITY   (China)

Author keywords

Glycidyl butyrate; Novozym 435; Porcine pancreatic lipase; Resolution; Two step

Indexed keywords

CATALYSIS; ESTERIFICATION; HYDROLYSIS; PARAFFINS;

GLYCIDYL BUTYRATE; NOVOZYM 435; PORCINE PANCREATIC LIPASE; TWO-STEP;

ENZYMES;

SUS;

EID: 34547941216     PISSN: 13595113     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.procbio.2007.06.012     Document Type: Article

References (44)

1. Kloosterman M., Elferink V.H.M., Vaniersel J., Roskam J.H., Meijer E.M., Hulshof L.A., et al. Lipases in the preparation of β-blockers. Trends Biotechnol 6 (1988) 251-256
2. Kasai N., Suzuki T., and Furukawa Y. Chiral C3 epoxides and halohydrins: their preparation and synthetic application. J Mol Catal B: Enzym 4 (1998) 237-252
3. Palomo J.M., Segura R.L., Mateo C., Terreni M., Guisan J.M., and Fernandez-Lafuente R. Synthesis of enantiomerically pure glycidol via a fully enantioselective lipase-catalyzed resolution. Tetrahedron: Asymmetry 16 (2005) 869-874
4. Brickner S.J., Hutchinson D.K., Barbachyn M.R., Manninen P.R., Ulanowicz D.A., Garmon S.A., et al. Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrug-resistant Gram-positive bacterial infections. J Med Chem 39 (1996) 673-679
5. Weidner-Wells M.A., Boggs C.M., Foleno B.D., Melton J., Bush K., Goldschmidt R.M., et al. Novel piperidinyloxy oxazolidinone antibacterial agents. diversification of the N-substituent. Bioorgan Med Chem 10 (2002) 2345-2351
6. Matsuda M., Endo Y., Fushiya S., Endo T., and Nozoe S. Cytotoxic 6-substituted 5,6-dihydro-2H-pyran-2-ones from a brazilian medicinal plant, chorisia-crispiflora. Heterocycles 38 (1994) 1229-1232
7. Waechter A.I., Ferreira M.E., Fournet A., Rojas de Arias A., Nakayama H., Torres S., et al. Experimental treatment of cutaneous leishmaniasis with argentilactone isolated from Annona haematantha. Planta Med 63 (1997) 433-435
8. Lozano P., De Diego T., Carrie D., Vaultier M., and Iborra J.L. Synthesis of glycidyl esters catalyzed by lipases in ionic liquids and supercritical carbon dioxide. J Mol Catal A-Chem 214 (2004) 113-119
9. Li C., Liu Q., Song X., Ding D., Ji A., and Qu Y. Epoxide hydrolase-catalyzed resolution of ethyl 3-phenylglycidate using whole cells of Pseudomonas sp. Biotechnol Lett 25 (2003) 2113-2116
10. Jia S., Xu J., Li Q., and Yu J. Isolation of lipase producer and its performance in enantioselective hydrolysis of glycidyl butyrate. Appl Biochem Biotech 104 (2003) 69-79
11. Schmid R.D., and Verger R. Lipases: interfacial enzymes with attractive applications. Angew Chem Int Ed 37 (1998) 1609-1633
12. Brady L., Brzozowski A.M., Derewenda Z.S., Dodson E., Dodson G., Tolley S., et al. A serine protease triad forms the catalytic centre of a triacylglycerol lipase. Nature 343 (1990) 767-770
13. Sarda L., and Desnuelle P. Action de la lipase pancreatique sur les esters en emulsion. Biochim Biophys Acta 30 (1958) 513-521
14. Magnusson A., Hult K., and Holmquist M. Creation of an enantioselectivity hydrolase by engineering substrate-assisted catalysis. J Am Chem Soc 123 (2001) 4354-4355
15. Derewenda U., Brzozowski A.M., Lawson D.M., and Derewenda ZS. Catalysis at the interface: the anatomy of a conformational change in a triglyceride lipase. Biochemistry 31 (1992) 1532-1541
16. Pregnolato M., Terreni M., de Fuentes I.E., Leon A.R.A., Sabuquillo P., Fernandez-Lafuente R., et al. Enantioselective enzymatic hydrolysis of racemic glycidyl esters by using immobilized porcine pancreas lipase with improved catalytic properties. J Mol Catal B: Enzym 11 (2001) 757-763
17. Ladner W.E., and Whitesides G.M. Lipase-catalyzed hydrolysis as a route to esters of chiral epoxy alcohols. J Am Chem Soc 106 (1984) 7250-7251
18. Crosby J. Chirality in Industry (1992), Wiley, Chichester p. 1
19. Palomo J.A., Segura R.L., Fuentes M., Ortiz C.C., Guisan J.M., and Fernandez-Lafuente R. Unusual enzymatic resolution of (+/-)-glycidyl-butyrate for the production of (S)-glycidyl derivatives. Enzyme Microb Technol 38 (2006) 429-435
20. Wandel U., Machado S.S., Jongejan J.A., and Duine J.A. Enzymes involved in the glycidaldehyde (2,3-epoxy-propanal) oxidation step in the kinetic resolution of racemic glycidol (2,3-epoxy-1-propanol) by Acetobacter pasteurianus. Enzyme Microb Technol 28 (2001) 233-239
21. Vanttinen E., and Kanerva L.T. Optimized double kinetic resolution for the preparation of (S)-solketal. Tetrahedron: Asymmetry 8 (1997) 923-933
22. Fishman A., Eroshov M., Dee-Noor S.S., van Mil J., Cogan U., and Effenberger R. A two-step enzymatic resolution process for large-scale production of (S)- and (R)-ethyl-3-hydroxybutyrate. Biotechnol Bioeng 74 (2001) 256-263
23. Cong F.D., Wang Y.H., Ma C.Y., Yu H.F., Han S.P., Tao J., et al. A way for resolution of (R,S)-2-octanol by combining dynamic kinetic resolution with double kinetic resolution. Enzyme Microb Technol 36 (2005) 595-599
24. Zada A., and Harel M. Enzymatic transesterification of racemic lavandulol: preparation of the two enantiomeric alcohols and of the two enantiomers of lavandulyl senecioate. Tetrahedron: Asymmetry 15 (2004) 2339-2343
25. Yu D.H., Wang Z., Zheng L.Y., Zhang G.R., and Cao S.G. Screening the reaction system for enzymatic resolution of glycidyl butyrate. Chin J Bioproc Eng 2 (2004) 40-43
26. Ma L., Persson M., and Adlercreutz P. Water activity dependence of lipase catalysis in organic media explains successful transesterification reactions. Enzyme Microb Technol 31 (2002) 1024-1029
27. Halling P.J. Salt hydrates for water activity control with biocatalyst in organic media. Biotechnol Tech 6 (1992) 271-276
28. 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
29. Segura R.L., Betancor L., Palomo J.M., Hidalgo A., Fernandez-Lorente G., Terreni M., et al. Purification and identification of different lipases contained in PPL commercial extracts: a minor contaminant is the main responsible of most esterasic activity. Enzyme Microb Technol 39 (2006) 817-823
30. Veeraragavan K. A simple and sensitive method for the estimation of microbial lipase activity. Anal Biochem 186 (1990) 301-305
31. Liu Y.Y., Xu J.H., and Hu Y. Enhancing effect of Tween-80 on lipase performance in enantioselective hydrolysis of Ketoprofen ester. J Mol Catal B: Enzym 10 (2000) 523-529
32. Kamiya N., Kasagi H., Inoue M., Kusunoki K., and Goto M. Enantioselective recognition mechanism of secondary alcohol by surfactant-coated lipases in nonaqueous media. Biotechnol Bioeng 65 (1999) 227-232
33. Klibanov A.M. Enzymes that work in organic solvents. Chemtech 16 (1986) 354-359
34. Okazaki S., Kamiya N., Abe K., Goto M., and Nakashio F. Novel preparation method for surfactant-lipase complexes utilizing water in oil emulsions. Biotechnol Bioeng 55 (1997) 455-460
35. Fernandez-Lorente G., Palomo J.M., Fuentes M., Mateo C., Guisan J.M., and Fernandez-Lafuente R. Self-assembly of Pseudomonas fluorescens lipase into bimolecular aggregates dramatically affects functional properties. Biotechnol Bioeng 82 (2003) 232-237
36. Fernandez-Lorente G., Palomo J.M., Mateo C., Munilla R., Ortiz C., Cabrera Z., et al. Glutaraldehyde cross-linking of lipases adsorbed on aminated supports in the presence of detergents leads to improved performance. Biomacromolecules 7 (2006) 2610-2615
37. Mingarro I., Abad C., and Braco L. Interfacial activation-based molecular bioimprinting of lipolytic enzymes. Proc Natl Acad Sci USA 92 (1995) 3308-3312
38. Laane C., Boeren S., Vos K., and Veeger C. Rules for optimization of biocatalysis in organic solvents. Biotechnol Bioeng 30 (1987) 81-87
39. Giacometti J., and Giacometti F. Study of organic solvent hydrophobicity on lipase catalyzed reaction-esterification. Biotechnol Bioeng 20 (2006) 269-274
40. Janssen A.E.M., Sjursnes B.J., Vakurov A.V., and Halling P.J. Kinetics of lipase-catalyzed esterification in organic media: correct model and solvent effects on parameters. Enzyme Microb Technol 24 (1999) 463-470
41. Halling P.J. Thermodynamic predictions for biocatalysis in nonconventional media: theory, tests, and recommendations for experimental design and analysis. Enzyme Microb Technol 16 (1994) 178-206
42. Halling P.J. Enzymatic conversions in organic and other low-water media. In: Drauz K., and Waldmann H. (Eds). Handbook of Enzyme Catalysis in Organic Synthesis. (2002), Wiley-VCH Verlag GmbH, Weinheim, Germany 259-286
43. Wehjte E., Costes D., and Adlercreutz P. Enantioselectivity of lipases: effects of water activity. J Mol Catal B: Enzym 3 (1997) 221-230
44. Persson M., Costes D., Wehtje E., and Adlercreutz P. Effects of solvent, water activity and temperature on lipase and hydroxynitrile lyase enantioselectivity. Enzyme Microb Technol 30 (2002) 916-923