Continuous enantioselective esterification of trans-2-phenyl-1- cyclohexanol using a new Candida rugosa lipase in a packed bed bioreactor

Journal of Biotechnology

Volumn 84, Issue 1, 2000, Pages 1-12

  Sánchez, Antoni ^a   Del Río, José Luis ^b   Valero, Francisco ^a   Lafuente, Javier ^a   Faus, Ignasi ^b   Solà, Carles ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b URQUIMA SA Uriach Group   (Spain)

Author keywords

Batch bioreactor; Candida rugosa lipase; Esterification; Experimental design; Kinetics; Packed bed bioreactor; Trans 2 Phenyl 1 cyclohexanol

Indexed keywords

BIOCATALYSTS; BIOREACTORS; ENZYME IMMOBILIZATION; ENZYME KINETICS; FERMENTATION; PACKED BEDS; POLYPROPYLENES;

ENANTIOSELECTIVE ESTERIFICATION; PACKED BED BIOREACTORS;

ESTERIFICATION;

ACID; ALCOHOL; CYCLOHEXANOL DERIVATIVE; OCTANE; SOLVENT; TRIACYLGLYCEROL LIPASE;

ARTICLE; BIOREACTOR; CANDIDA RUGOSA; CATALYST; CHEMICAL REACTION KINETICS; ESTERIFICATION; METHODOLOGY; MICHAELIS MENTEN KINETICS; NONHUMAN; PRIORITY JOURNAL; STEREOCHEMISTRY;

BIOREACTORS; CANDIDA; CYCLOHEXANOLS; ENZYMES, IMMOBILIZED; ESTERIFICATION; ESTERS; KINETICS; LIPASE; MODELS, CHEMICAL; STEREOISOMERISM; SUPPORT, NON-U.S. GOV'T;

EID: 0343442484     PISSN: 01681656     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0168-1656(00)00318-7     Document Type: Article

References (39)

1. Arroyo M., Sinisterra J.V. High enantioselective esterification of 2-arylpropionic acids catalyzed by immobilized lipase from Candida antarctica: a mechanistic approach. J. Org. Chem. 59:1994;4410-4417.
2. Arroyo R., Sánchez-Muñiz F.J., Cuesta C., Burguillo F.J., Sánchez-Montero J.M. Hydrolysis of used frying palm olein and sunflower oil catalyzed by porcine pancreatic lipase. Lipids. 31:1996;1133-1139.
3. Balcao V.M., Malcata F.X. Interesterification and acidolysis of butterfat with oleic acid by Mucor javanicus lipase: changes in the pool of fatty acid residues - influence on the free fatty acid profile. Enzyme Microb. Technol. 22:1998;511-519.
4. Balcao V.M., Paiva A.L., Malcata F.X. Bioreactors with immobilized lipases: state of the art. Enzyme Microb. Technol. 18:1996;392-416.
5. Basavaiah D., Rao P.D. Enzymatic resolution of trans-2-arylcyclohexan-1-ols using crude chicken liver esterase (CCLE) as biocatalyst. Tetrahedron: Asymmetry. 5:1994;223-234.
6. Battistel E., Bianchi D., Cesti P., Pina C. Enzymatic resolution of (S)-(+)-Naproxen in a continuous reactor. Biotechnol. Bioeng. 38:1991;659-664.
7. Botta M., Cernia E., Corelli F., Manetti F., Soro S. Probing the substrate specificity for lipases. II: kinetic and modelling studies on the molecular recognition of 2-arylpropionic esters by Candida rugosa and Rhizomucor miehei lipases. Biochim. Biophys. Acta. 1337:1997;302-310.
8. Box G.E.P., Hunter W.G., Hunter J.S. Estadística para investigadores. 1st Edition :1988;Reverté Barcelona.
9. Capellas M., Benaiges M.D., Caminal G., González G., López-Santín J., Clapés P. Influence of water activity and support material on the enzymatic synthesis of a CCK-8 tripeptide fragment. Biocatal. Biotransform. 13:1996;165-178.
10. Carpenter B.E., Hunt I.R., Keay B.A. A short efficient preparation of (+) and (-)-trans-2-phenylcyclohexanol. Tetrahedron: Asymmetry. 7:1996;3197-3198.
11. Carvalho C.M.L., Serralherio M.L.M., Cabral J.M.S., Aires-Barros M.R. Application of factorial design to the study of transesterification reactions using cutinase in AOT-reversed micelles. Enzyme Microb. Technol. 21:1997;117-123.
12. Chen C.S., Sih C.J. General aspects and optimization of enantioselective biocatalysis in organic solvent. Angew. Chem. Int. Ed. Engl. 28:1989;695-707.
13. Chen J., Wang J. Wax ester synthesis by lipase-catalyzed esterification with fungal cells immobilized on cellulose biomass support particles. Enzyme Microb. Technol. 20:1997;615-622.
14. Chen C.S., Fujimoto Y., Girdaukas G., Sih C.J. Quantitative analyses of biochemical kinetic resolutions of enantiomers. J. Am. Chem. Soc. 104:1982;7294-7299.
15. Chulalaksananukul W., Condoret J.S., Delorme P., Willemot R.M. Kinetic study of esterification by immobilized lipase in hexane. FEBS Lett. 276:1990;181-184.
16. Del Río J.L., Faus I. Resolution of (±)-trans-2-phenylcyclohexan-1-ol by lipases from Candida rugosa: effect of catalyst source and reaction conditions. Biotechnol. Lett. 20:1998;1021-1025.
17. Faber K. Biotransformations in Organic Chemistry. 2nd Edition :1995;Springer, Berlin.
18. García M., Gradillas A., Del Campo C., Llama E.F., Sánchez-Montero J.M., Sinisterra J.V. Hydrolysis of 2-substituted aryl and heteroaryl alkanoates by Candida rugosa lipase. Biotechnol. Lett. 19:1997;999-1004.
19. Gargouri Y., Chahinian H., Moreau H., Ransac S., Verger R. Inactivation of pancreatic and gastric lipases by THL and C12:0-TNB: a kinetic study with emulsified tributyrin. Biochim. Biophys. Acta. 1085:1991;322-328.
20. Gitlesen T., Bauer M., Adlercreutz P. Adsorption of lipase on polypropylene powder. Biochim. Biophys. Acta. 1345:1997;188-196.
21. Gordillo M.A., Obradors N., Montesinos J.L., Valero F., Lafuente J., Solà C. Stability studies and effect of the initial oleic acid concentration on lipase production by Candida rugosa lipase. Appl. Microbiol. Biotechnol. 43:1995;38-41.
22. Gordillo M.A., Sanz A., Sánchez A., Valero F., Montesinos J.L., Lafuente J., Solà C. Enhancement of Candida rugosa lipase production by using different control fed-batch operational strategies. Biotechnol. Bioeng. 60:1998;156-168.
23. Jaeger K.E., Ransac S., Dijkstra B.W., Colson C., Heuvel v.M., Misset O. Bacterial lipases. FEMS Microbiol. Rev. 15:1994;29-63.
24. López-Belmonte M.T., Alcántara A.R., Sinisterra J.V. Enantioselective esterification of 2-aryl propionic acids catalyzed by immobilized Rhizomucor miehei lipase. J. Org. Chem. 62:1997;1831-1840.
25. Lundell K., Raijola T., Kanerva L.T. Enantioselectivity of Pseudomonas cepacia and Candida rugosa lipases for the resolution of secondary alcohols: the effect of Candida rugosa isoenzymes. Enzyme Microb. Technol. 22:1998;86-93.
26. Matsumae H., Furui M., Shibatani T. Production of optically active 3-phenylglycidic acid ester by the lipase from Serratia marcescens on a hollow fiber membrane reactor. J. Ferment. Bioeng. 78:1994;59-63.
27. Montesinos J.L., Obradors N., Gordillo M.A., Valero F., Lafuente J., Solà C. Effect of nitrogen sources in batch and continuous cultures to lipase production by Candida rugosa. Appl. Biochem. Biotechnol. 59:1996;25-37.
28. Rapp P., Backhaus S. Formation of extracellular lipase by filamentous fungi, yeasts and bacteria. Enzyme Microb. Technol. 4:1992;938-943.
29. Rosell C.M., Vaidya A.M., Halling P.J. Continuous in situ water activity control for organic phase biocatalysis in a packed bed hollow fiber reactor. Biotechnol. Bioeng. 49:1996;284-289.
30. Sánchez A., Valero F., Lafuente J., Solà C. Enantioselective esterification of 2-arylpropionic acids and trans-2-phenyl-1-cyclohexanol: comparison between immobilised lipases from Candida rugosa and Rhizomucor miehei. Biotechnol. Lett. 20:1998;1145-1148.
31. Sánchez A., Ferrer P., Serrano A., Pernas M.A., Valero F., Rúa M.L., Casas C., Solà C. Characterisation of the lipase and esterase multiple forms in a enzyme preparation from a Candida rugosa pilot plant scale fed-batch fermentation. Enzyme Microb. Technol. 25:(3-5):1999;214-223.
32. Sánchez A., Ferrer P., Serrano A., Valero F., Solà C., Pernas M., Rúa M.L., Fernández-Lafuente R., Guisán J.M., De la Casa R.M., Sinisterra J.V., Sánchez-Montero J.M. A controlled fed-batch cultivation for the production of new crude lipases from Candida rugosa with improved properties in fine chemistry. J. Biotechnol. 69:1999;169-182.
33. Sánchez A., De la Casa R., Sinisterra J.V., Valero F., Sánchez-Montero J.M. Effect of fermentation conditions in the enzymatic activity and stereoselectivity of crude lipase from Candida rugosa. Appl. Biochem. Biotechnol. 80:1999;65-75.
34. Santaniello E., Ferraboschi P., Grisenti P. Lipase-catalysed transesterification in organic solvents: applications to the preparation of enantiomerically pure compounds. Enzyme Microb. Technol. 15:1993;367-382.
35. Schoffers E., Golebiowski A., Johnson C.R. Enantioselective synthesis through enzymatic asymmetrization. Tetrahedron. 52:1996;3769-3826.
36. Sorensen, J.H., Arlt, W., 1979. Liquid-liquid Equilibrium Data Collection. Binary Systems, 1st Edition, Dechema Chemistry Data Series, vol. V, Part I.
37. Tawaki S.H., Klibanov A.M. Chemoselectivity of enzymes in anhydrous media is strongly solvent dependent. Biocatalysis. 8:1993;3-19.
38. Wehtje E., Kaur J., Adlercreutz P., Chand S., Mattiason B. Water activity control in enzymatic esterification processes. Enzyme Microb. Technol. 21:1997;502-510.
39. Whitesell J.K. Cyclohexyl-based chiral auxiliaries. Chem. Rev. 92:1992;953-964.