Kinetic and enantioselective behaviour of isoenzymes A and B from Candida rugosa lipase in the hydrolysis of lipids and esters

Biocatalysis and Biotransformation

Volumn 15, Issue 2, 1997, Pages 75-89

  Plou, Francisco J ^a   Sogo, Pedro ^b   Calvo, María V ^a   Burguillo, Francisco J ^b   Ballesteros, Antonio ^a  

^a CSIC   (Spain)

^b UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

Candida rugosa; Enantiomeric excess; Enantioselectivity; Enzyme kinetics; Lipase isoenzymes

Indexed keywords

CATALYST ACTIVITY; CATALYST SELECTIVITY; CHLORINE COMPOUNDS; ESTERS; HYDROLYSIS; LIPIDS; NITROGEN COMPOUNDS; PURIFICATION; REGRESSION ANALYSIS;

ENANTIOSELECTIVITY; LIPASE; METHYL CHLOROPROPIONATE; NITROPHENYL ACETATE; STEREOSPECIFICITY; TRIBUTYRIN;

ENZYME KINETICS;

ACID LIPASE; BUTYRIC ACID DERIVATIVE; ESTER; ESTERASE; ISOENZYME; LIPID; PHENYLACETIC ACID; PROPIONIC ACID DERIVATIVE; TRIACYLGLYCEROL LIPASE;

AREA UNDER THE CURVE; ARTICLE; CANDIDA RUGOSA; ENANTIOMER; ENZYME ACTIVITY; ENZYME KINETICS; ENZYME SPECIFICITY; ENZYME SUBSTRATE; HYDROLYSIS; NONHUMAN;

CANDIDA RUGOSA; FELIS CATUS;

EID: 0031447887     PISSN: 10242422     EISSN: None     Source Type: Journal    
DOI: 10.3109/10242429709003611     Document Type: Article

References (41)

1. Allenmark, S. and Ohlsson, A. (1992) Studies of the heterogeneity of a Candida cylindracea (rugosa) lipase: Monitoring of esterolytic activity and enantioselectivity by chiral liquid chromatography. Biocatalysis 6, 211-221.
2. Ballesteros, A., Bernabe, M., Cruzado, C., Martin-Lomas, M. and Otero, C. (1989) Regio-selective deacylation of 1,6-anhydro-β-D-galactopyranose derivatives catalyzed by soluble and immobilized lipases. Tetrahedron 45, 7077-7082.
3. Bardsley, G.W. (1993) SIMFIT: A package for simulation, curve-fitting and statistical analysis in the life sciences, Manchester University, U.K.
4. Bianchi, D., Battistel, E., Bosetti, A., Cesti, P. and Fekete, Z. (1993) Effects of chemical modification on stereoselectiviy of Pseudomonas cepacia lipase. Tetrahedron: Asymmetry 5, 777-782.
5. Borgstroem, B. and Brockman, H.L. (1984) Lipases. Elsevier Science Publishers, Amsterdam.
6. Brahimi-Horn, M., Guglielmino, M.L., Elling, L., Sparrow, L.G. (1990) The esterase profile of a lipase from Candida cylindrica. Biochim. Biophys. Acta 1042, 51-54.
7. Brocca, S., Grandori, R., Breviario, D. and Lotti, M. (1995) Localization of lipase genes on Candida rugosa chromosomes. Curr. Genet. 28, 454-457.
8. Cambou, B. and Klibanov, A.M. (1984) Comparison of different strategies for the lipase-catalyzed preparative resolution of racemic acids and alcohols: asymmetric hydrolysis, esterification and transesterification. Biotechnol. Bioeng. 26, 1449-1454.
9. Carta, G., Gainer, J.L. and Benton, A.H. (1991) Enzymatic synthesis of esters using an immobilized lipase. Biotech. Bioeng. 37, 1004-1009.
10. Chen, C.S., Fujimoto, Y., Girdaukas, G. and Sih, C.J. (1982) Quantitative analyses of biochemical kinetic resolutions of enantiomers. J. Am. Chem. Soc. 104, 7294-7299
11. Chen, P.Y., Wu, S.H. and Wang, K.T. (1993) Double enantioselective esterification of racemic acids and alcohols by lipase from Candida rugosa. Biotechnol. Lett. 15, 181-184.
12. Dahod, S.K. and Siuta-Mangano, P. (1987) Carbon tetrachloride-promoted stereoselective hydrolysis of methyl-2-chloropropionate by lipase. Biotechnol. Bioeng. 30, 995-999.
13. Dixon, M. and Webb, E.C. (1979) Enzymes, 3rd Edn., pp. 72-75. Longman, London.
14. Faber, K. and Franssen, M.C.R. (1993) Prospects for the increased application of biocatalysts in organic solvents. Trends Biotechnol. 11, 461-470.
15. Geluk, M.A., Norde, W., Van Kalsbeek, H.K.A.I. and Van't Riet, K. (1992) Adsorption of lipase from Candida rugosa on cellulose and its influence on lipolytic activity. Enzyme Microb. Technol. 14, 748-754.
16. Hernaiz, M.J., Sanchez-Montero, J.M. and Sinisterra, J.V. (1995) Hydrolysis of (R,S)-2-aryl propionic esters by pure lipase B from Candida cylindracea. J. Mol. Catal. A: Chemical 96, 317-327
17. Iwai, M., Tsujisaka, Y. and Tominaga, Y. (1979) Increase in the activity of Rhizopus C-lipase on lipoprotein by its interaction with phospholipid. Agric Biol. Chem. 43, 893-900.
18. Jensen, R.G., Galluzas, D.R. and Bush, V.J. (1990) Selectivity is an important characteristic of lipases (acylglycerol hydrolases). Biocatalysis 3, 307-316.
19. Kazlaukas, R.J. (1993) Elucidating structure-mechanism relationships in lipases: prospects for predicting and engineering catalytic properties. Trends Biotechnol 11, 439-440.
20. Kotting, J., Jurgens, D. and Huser, H. (1983) Separation and characterization of two isolated lipases from Staphylococus aureus (TENS). J. Chromatogr. 281, 253-261.
21. Lalonde, J.J., Govardhan, C., Khalaf, N., Martínez, A.G., Visuri, K. and Margolin, A.L. (1995) Cross-linked crystals of Candida rugosa lipase highly efficient catalysts for the resolution of chiral esters. J. Am. Chem. Soc. 117, 6845-6852.
22. Linko, Y-Y. and Wu, X.Y. (1996) Biocatalytic production of useful esters by two forms of lipase from Candida rugosa. J. Chem. Tech. Biotechnol. 65, 163-170.
23. Lotti, M., Tramontano, A., Longhi, S., Fusetti, F., Brocca, S., Pizzi, E. and Alberghina, L. (1994) Variability within the Candida rugosa lipases family. Protein Eng. 7, 531-537.
24. Lowry, O.H., Rosebrough, N.J., Farr, A.L. and Randall, R. (1951) Protein measurement with the Folin phenol reagent. J Biol. Chem. 193, 256-275.
25. Malcata, F.X., Reyes, H.R., Garcia, H.S., Hill, C.G.Jr. and Amundson, C.H. (1990) Immobilized lipase reactors for modification of fats and oils: A review. J. Am. Oil Chem. Soc. 67, 890-910.
26. Martinelle, M. and Hult, K. (1994) Kinetics of triglyceride lipases. In: Lipases, Their Structure, Biochemistry and Application (Woodley, P. and Petersen, S.B., eds.), pp. 159-180. Cambridge University Press, Cambridge.
27. Mustranta, A. (1992) Use of lipases in the resolution of racemic ibuprofen. Appl. Microbiol. Biot. 38, 61-66.
28. Otero, C., Pastor, E. and Ballesteros, A. (1990) Synthesis of monobutyrylglycerol by transesterification with soluble and immobilized lipases. Appl. Biochem Biotechnol. 26, 35-44.
29. Ottolina, G., Carrea, G., Riva, S., Sartore, L. and Veronese, F.M. (1992) Effect of the enzyme form on the activity, stability and enantioselectivity of lipoprotein lipase in toluene. Biotechnol. Lett. 17, 171-176.
30. Parida, S. and Dordick, J.S. (1991) Substrate structure and solvent hydrophobicity control lipase catalysis and enantioselectivity in organic media. J. Am. Chem. Soc. 113, 2253-2259.
31. Persichetti, R.A., Lalonde, J.J., Govardhan, C.P., Khalaf, N.K. and Margolin, A.L. (1996) Candida rugosa lipase: enantioselectivity enhancements in organic solvents. Tetrahedron Lett. 37, 6507-6510.
32. Rakels, J.L.L., Straathof, A.J.J. and Heijnen, J.J. (1993) A simple method to determine the enantiomeric ratio in enantioselective biocatalysis. Enzyme Microb. Technol. 15, 1051-1056.
33. Redondo, O., Herrero, A., Bello, J.F., Roig, M.G., Calvo, M. V., Plou, F. J. and Burguillo, F.J. (1995) Comparative kinetic study of lipases A and B from Candida rugosa in the hydrolysis of lipid p-nitrophenyl esters in mixed micelles with Triton X-100. Biochim. Biophys. Acta 1243, 15-24
34. Reyes, H.R. and Hill, C.G.Jr. (1994) Kinetics modelling of interesterification reactions catalyzed by immobilized lipase. Biotech. Bioeng. 43, 171-182.
35. Rua, M.L. and Ballesteros, A. (1992) Spanish patent 9201378. International extension PCT/ES93/00058 (1993).
36. Rua, M.L., Díaz-Mauriño, T., Fernández, V.M., Otero, C. and Ballesteros, A. (1993) Purification and characterization of two distinct lipases from Candida cylindracea. Biochim. Biophys. Acta 1156, 181-189.
37. Rua, M. L. and Ballesteros, A. (1994) Rapid purification of two lipase isoenzymes from Candida rugosa. Biotechnol. Techn. 8, 21-26.
38. Sánchez, E.M., Bello, J.F., Roig, M.G., Burguillo, F.J., Moreno, J.M. and Sinisterra, J.V. (1996) Kinetic and enantioselective behaviour of the lipase from Candida cylindracea: a comparative study between the soluble enzyme and the enzyme immobilized on agarose and silica gels. Enzyme Microb. Technol. 18, 468-476.
39. Van Oort, M.G., Deveer, S.M.Th.J., Dijkman, R., Tjeenk, M.L., Vrheij, H.M., De Haas, G.H., Wenzig, E. and Gotz, F. (1989) Purification and substrate specificity of Staphylococcus hyicus lipase. Biochemistry 28, 9278-9285.
40. Veeraragavan, K. and Gibbs, B.F. (1989) Detection and partial purification of two isoenzymes from Candida rugosa. Biotechnol Lett. 11, 345-348.
41. Wu, S.H., Guo, Z.W. and Sih, C.J. (1990) Enhancing the enantioselectivity of Candida lipase catalyzed ester hydrolysis via noncovalent enzyme modification. J. Am. Chem. Soc. 112, 1990-1995.