Substrate specificity and kinetics of Candida rugosa lipase in organic media

Enzyme and Microbial Technology

Volumn 18, Issue 5, 1996, Pages 340-346

  Janssen, Anja E M ^a,b   Vaidya, Atul M ^a   Halling, Peter J ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

Esterification; Lipase specificity; Organic solvent; Ping Pong kinetics; Solvation

Indexed keywords

ALCOHOL; FATTY ACID; ORGANIC SOLVENT; SATURATED FATTY ACID; SULCATOL; TOLUENE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; CANDIDA; CANDIDA RUGOSA; CULTURE MEDIUM; ENZYME ACTIVITY; ENZYME KINETICS; ENZYME SPECIFICITY; ESTERIFICATION; FUNGUS CULTURE; NONHUMAN; SOLVATION;

EID: 0029922329     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/0141-0229(95)00075-5     Document Type: Article

References (34)

1. Zaks, A., and Klibanov, A. M. Substrate specificity of enzymes in organic solvents vs. water is reversed. J. Am. Chem. Soc. 1986, 108, 2767-2768
2. Clapes, P., and Adlercreutz, P. Substrate specificity of α-chymotrypsin-catalyzed esterification in organic media. Biochim. Biophys. Acta 1991, 1118, 70-76
3. Nagashima, T., Watanabe, A., and Kise, H. Peptide synthesis by proteases in organic solvents: Medium effect on substrate specificity. Enzyme Microb. Technol. 1992, 14, 842-847
4. Gaertner, H., and Puigserver, A. Kinetics and specificity of serine proteases in peptide synthesis catalyzed in organic solvents. Eur. J. Biochem. 1989, 181, 207-213
5. Ryu, K., and Dordick, J. S. Free energy relationships of substrate and solvent hydrophobicities with enzymatic catalysis in organic media. J. Am. Chem. Soc. 1989, 111, 8026-8027
6. Bell, R. P., Critchlow, J. E., and Page, M. I. Ground state and transition state effects in the acylation of α-chymotrypsin in organic solvent-water mixtures. J. Chem. Soc., Perkin Trans. 2 1974, 66-70
7. Maurel, P. Relevance of dielectric constant and solvent hydrophobicity to the organic solvent effect in enzymology. J. Biol. Chem. 1978, 253, 1677-1683
8. Ryu, K., and Dordick, J. S. How do organic solvents affect peroxidase structure and function? Biochemistry 1992, 31, 2588-2598
9. Dordick, J. S. Designing enzymes for use in organic solvents. Biotechnol. Prag. 1992, 8, 259-267
10. Parida, S., and Dordick, J. S. Tailoring lipase specificity by solvent and substrate chemistries. J. Org. Chem. 1993, 58, 3238-3244
11. Wescott, C. R., and Klibanov, A. M. Solvent variation inverts substrate specificity of an enzyme. J. Am. Chem. Soc. 1993, 115, 1629-1631
12. Wescott, C. R., and Klibanov, A. M. Predicting the solvent dependence of enzymatic substrate specificity using semiempirical thermodynamic calculations. J. Am. Chem. Soc. 1993, 115, 10362-10363
13. Janssen, A. E. M., and Halling, P. J. Specificities of enzymes "corrected for solvation" depend on the choice of the standard state. J. Am. Chem. Soc. 1994, 116, 9827-9830
14. Straathof, A. J. J., Rakels, J. L. L., and Heijnen, J. J. Enzyme kinetics in monophasic and biphasic aqueous-organic systems. In: Biocatalysis in Non-Conventional Media (Tramper, J., Vermue, M. H., Beeftink, H. H., and von Stockar, U., eds.) Elsevier, Amsterdam, 1992, 137-144
15. Van Tol, J. B. A., Odenthal, J. B., Jongejan, J. A., and Duine, J. A. Relation of enzymatic reaction rate and hydrophobicity of the solvent. In: Biocatalysis in Non-Conventional Media (Tramper, J., Vermue, M. H., Beeftink, H. H., and von Stockar, U., eds.) Elsevier, Amsterdam, 1992, 229-235
16. Hailing, P. J. Thermodynamic predictions for biocatalysis in non-conventional media: Theory, tests, and recommendations for experimental design and analysis. Enzyme Microb. Technol. 1994, 16, 178-206
17. Reimann, A., Robb, D. A., and Halling, P. J. Solvation of CBZ-amino acid nitrophenyl esters in organic media and the kinetics of their transesterification by subtilisin. Biotechnol. Bioeng. 1994, 43, 1081-1086
18. Rangheard, M.-S., Langrand, G., Triantaphylides, C., and Baratti, J. Multi-competitive enzymatic reactions in organic media: A simple test for the determination of lipase fatty acid specificity. Biochim. Biophys. Acta 1989, 1004, 20-28
19. Rangheard, M.-S., Langrand, G., Triantaphylides, C., and Baratti, J. Multi-competitive enzymatic reactions in organic media: Application to the determination of lipase alcohol specificity. Enzyme Microb. Technol. 1992, 14, 966-974
20. Chatterjee, S., and Russell, A. J. Determination of equilibrium and individual rate constants for subtilisin-catalyzed transesterification in anhydrous environments. Biotechnol. Bioeng. 1992, 40, 1069-1077
21. Rizzi, M., Stylos, P., Riek, A., and Reuss, M. A kinetic study of immobilized lipase catalyzing the synthesis of isoamyl acetate by transesterification in n-hexane. Enzyme Microb. Technol. 1992, 14, 709-714
22. Valivety, R. H., Halling, P. J., and Macrae, A. R. Water as a competitive inhibitor of lipase-catalysed esterification in organic media. Biotechnol. Lett. 1993, 15, 1133-1138
23. Miller, D. A., Prausnitz, J. M., and Blanch, H. W. Kinetics of lipase-catalyzed interesterification of triglycerides in cyclohexane. Enzyme Microb. Technol. 1991, 13, 98-103
24. Mitsuda, S., and Nabeshima, S. Enzymatic optical resolution of a synthetic pyrethroid alcohol. Enantioselective transesterification by lipase in organic solvent. Recl. Trav. Chim. Pays-Bas 1991, 110, 151-154
25. Stamatis, H., Xenakis, A., Menge, U., and Kolisis, F. N. Kinetic study of lipase-catalyzed esterification reactions in water-in-oil emulsions. Biotechnol. Bioeng. 1993, 42, 931-937
26. 2. Biotechnol. Bioeng. 1992, 39, 273-280
27. Chulalaksananukul, W., Condoret, J. S., Delorme, P., and Willemot, R. M. Kinetic study of esterification by immobilized lipase in n-hexane. FEBS Lett. 1990, 276, 181-184
28. M of lipase catalyzed transesterification in organic media. Biotechnol. Lett. 1993, 15, 937-942
29. Valivety, R. H., Halling, P. J., Peilow, A. D., and Macrae, A. R. Lipases from different sources vary widely in dependence of catalytic activity on water activity. Biochim. Biophys. Acta 1992, 1122, 143-146
30. Valivety, R. H., Halling, P. J., and Macrae, A. R. Reaction rate with suspended lipase catalyst shows similar dependence on water activity in different organic solvents. Biochim. Biophys. Acta 1992, 1118, 218-222
31. Hansen, H. K., Rasmussen, P., Fredenslund, A., Schiller, M., and Gmehling, J. Vapor-liquid equilibria by UNIFAC group contribution. 5. Revision and extension. Ind. Eng. Chem. Res. 1991, 30, 2355-2358
32. Segel, I. H. Enzyme kinetics. Wiley, New York, 1975
33. Janssen, A. E. M., Van der Padt, A., Van Sonsbeek, H. M., and Van 't Riet, K. The effect of organic solvents on the equilibrium position of enzymatic acylglycerol synthesis. Biotechnol. Bioeng. 1993, 41, 95-103
34. Van Tol, J. B. A. Description of the kinetics and enantioselectivity of lipases in various media. Doctoral Thesis, Delft University of Technology, The Netherlands, 1994