Synthesis of lovastatin with immobilized Candida rugosa lipase in organic solvents: Effects of reaction conditions on initial rates

Biotechnology and Bioengineering

Volumn 56, Issue 6, 1997, Pages 671-680

  Yang, Fangxiao ^a   Weber, Timothy W ^a,b   Gainer, John L ^a   Carta, Giorgio ^a  

^a University of Virginia   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Candida rugosa lipase; Dielectric constant; Immobilized enzymes; Lovastatin; Organic solvents

Indexed keywords

ACYLATION; BINARY MIXTURES; CARBOXYLIC ACIDS; ENZYME IMMOBILIZATION; ESTERS; ORGANIC SOLVENTS; PARAFFINS; PERMITTIVITY; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CANDIDA RUGOSA; DIOL LACTONE; HEXANE; LIPASE; LOVASTATIN; METHYLBUTYRIC ACID;

DRUG PRODUCTS;

2 METHYLBUTYRIC ACID; ACETONE; BUTYRIC ACID DERIVATIVE; CHLOROFORM; DICHLOROMETHANE; FUNGAL PROTEIN; HEXANE; LACTONE DERIVATIVE; MEVINOLIN; ORGANIC SOLVENT; PROPIONIC ACID; TRIACYLGLYCEROL LIPASE;

ARTICLE; CANDIDA; DIELECTRIC CONSTANT; DRUG SYNTHESIS; ENZYME IMMOBILIZATION; REACTION ANALYSIS;

EID: 0342683791     PISSN: 00063592     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1097-0290(19971220)56:6<671::AID-BIT10>3.0.CO;2-B     Document Type: Article

References (40)

1. Affleck, R. Haynes, C. A., Clark, D. S. 1992a. Solvent dielectric effects on protein dynamics. Proc. Natl. Acad. Sci. USA 89: 5167-5170.
2. Affleck, R., Xu, Z.-F., Susawa, V., Focht, K., Clark, D. S., Dordick, J. S. 1992b. Enzymatic catalysis and dynamics in low-water environments. Proc. Natl. Acad. Sci. USA 89: 1100-1104.
3. Almarsson, O., Klibanov, A. M. 1996. Remarkable activation of enzymes in nonaqueous media by denaturing organic cosolvents. Biotechnol. Bioeng. 49: 87-92.
4. ASTM, 1996. Annual book of ASTM standards. Designation D 924-92, Vol. 10.03 American Society for Testing and Materials, West Conshohocken, PA.
5. Borzoix, F., Monot, F., Vandecasteele, T. P. 1992. Strategies for enzymatic esterification in organic solvents: Comparison of microaqueous, biphasic, and micellar systems. Enzyme Microb. Technol. 14: 791-797.
6. Burgess, K., Jennings, L. D. 1991. Enantioselective esterifications of unsaturated alcohols mediated by a lipase prepared from Psudomonas sp. J. Am. Chem. Soc. 113: 6129-6139.
7. Carta, G., Gainer, J. L., Gibson, M. E. 1992. Synthesis of esters using a nylon-immobilized lipase in batch and continuous flow reactors. Enzyme Microb. Technol. 14: 904-910.
8. Carta, G., Gainer, J. L., Benton, A. H. 1991. Enzymatic synthesis of esters using an immobilized lipase. Biotechnol. Bioeng. 37: 1004-1009.
9. Dordick, J. S. 1989. Enzymatic catalysis in monophasic organic solvents. Enzyme Microb. Technol. 11: 194-211.
10. Dordick, J. S. 1992. Designing enzymes for use in organic solvents. Biotechnol. Progr. 8: 259-267.
11. Endo, A. 1980. Monacolin K, a new hypocholesterolemic agent that specifically inhibits 3-hydroxy-3-methylglutaryl coenzyme A reductase. J. Antibiotics 33: 334-336.
12. Endo, A., Hasumi, K. 1985. Dihydromonacolin L and monacolin X, new metabolites that inhibit cholesterol biosynthesis. J. Antibiotics 38: 321-327.
13. Endo, A., Komagata, D., Shimoda, H. 1986. Monacolin M, a new inhibitor of cholesterol biosynthesis. J. Antibiotics 38: 1670-1673.
14. Furusaki, S. 1988. Engineering aspects of immobilized biocatalysts. J. Chem. Eng. Japan 21: 219-230.
15. Gmehling, J., Li, J., Shiller, M. 1993. A modified UNIFAC model. 2. Present parameter matrix and results for different thermodynamic properties. Ind. Eng. Chem. Research 32: 178-193.
16. Gutman, A. L., Meyer, E., Kalerin, E., Polyak, F., Sterling, J. 1992. Enzymatic resolution of racemic amines in a continuous reactor in organic solvents. Biotechnol. Bioeng. 40: 760-767.
17. Han, S., Rhee, J. S. 1986. Characteristics of lipase-catalyzed hydrolysis of olive oil in AOT-isooctane reversed micelles. Biotechnol. Bioeng. 28: 1250-1255.
18. Hilhorst, M. H., Spruijt, R., Laane, C., Veeger, C. 1984. Rules for the regulation of enzyme activity in reverse micelles as illustrated by the conversion of apolar steroids by 20 β-hydroxysteroid dehydrogenase. Eur. J. Biochem. 144: 459-466.
19. Hirama, M., Iwashita, M. 1983. Total synthesis of (+)-monacolin K (mevinolin). Tetrahedron Lett. 24: 1811-1812.
20. Hoffman, W. F., Alberts, A. W., Anderson, P. S., Chen, J. S., Smith, R. L., Willard, A. K. 1986. 3-Hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors. 4. Side chain ester derivatives of mevinolin. J. Med. Chem. 29: 849-852.
21. Jones, J. B. 1986. Enzymes in organic synthesis. Tetrahedron 42: 3351-3403.
22. Kimura, K., Komagata, D., Murakawa, S., Endo, A. 1990. Biosynthesis of monacolins: Conversion of monacolin J to monacolin K (mevinolin). J. Antibiotics 43: 1621-1622.
23. Kircher, G., Scollar, M. P., Klibanov, A. M. 1985. Resolution of racemic mixtures via lipase catalysis in organic solvent. J. Am. Chem. Soc. 107: 7072-7076.
24. Kolling, O. W. 1985. Nonlinear regression model for the representation of dielectric constants for binary aprotic solvents. Anal. Chem. 57: 1721-1725.
25. Laane, C., Boeren, S., Vos, K., Veeger, C. 1987. Rules for optimization of biocatalysis in organic solvents. Biotechnol. Bioeng. 30: 81-87.
26. Lehninger, A. L., Nelson, D. L., Cox, M. M. 1993. Biochemistry, 2nd edition, Worth Publishers, New York.
27. Lide, D. R. 1990. CRC handbook of chemistry and physics, 71st Edition. CRC Press, Boca Raton, FL.
28. Miller, C., Austin, H., Posorske, L., Gonzlez, J. 1988. Characteristics of an immobilized lipase for the commercial synthesis of esters. J. Am. OilChem. Soc. 65: 927-931.
29. Mustranta, A., Forssell, P., Poutanen, K. 1993. Applications of immobilized lipase to transesterification and esterification reactions in non-aqueous systems. Enzyme Microb. Technol. 15: 133-139.
30. Nakamura, T., Komagata, D., Murakawa, S., Sakai, K., Endo, A. 1990. Isolation and biosynthesis of 3a-hydroxy-3,5-dihydromonacolin L. J. Antibiotics 43: 1597-1600.
31. Parida, S., Dordick, J. S. 1993. Tailoring lipase specificity by solvent and substrate chemistries J. Org. Chem. 58: 3238-3244.
32. Perutz, M. F. 1978. Electrostatic effects in protein. Science 201: 1187-1191.
33. Rekker, R. F. 1977. The Hydrophobic fragmental constant, pp. 39-106. Elsevier, Amsterdam.
34. Sih, C. J., Gu, Q.-M., Fülling, G., Wu, S.-H., Reddy, D. R. 1988. The use of microbial enzymes for the synthesis of optically active pharmaceuticals. Dev. Ind. Microbiol. 29: 221-229.
35. Snijder-Lambers, A. M., Vultson, E. N., Doddema, H. J. 1991. Optimization of alcohol dehydrogenase activity and NAD(H) regeneration in organic solvents. Rend. Trav. Chim. Pays-Bas 110: 226-230.
36. van Vliet, A. K., van Thiel, G. C. F., Huisman, R. H., Moshage, H., Yap, S. H., Cohen, L. H. 1995. Different effect of 3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors on sterol synthesis in various human cell types. Biochim. Biophys. Acta 1254: 105-111.
37. Wangikar, P. P., Graycar, T. P., Estell, D. A., Clark, D. S., Dordick, J. S. 1993. Protein and solvent engineering of subtilisin BPN' in nearly anhydrous organic media. J. Am. Chem. Soc. 115: 12231-12237.
38. Weber, T. W. 1996. Synthesis of pharmaceuticals by direct esterification with immobilized enzymes. Ph.D. thesis, University of Virginia, Charlottesville, VA.
39. Yang, F.-X., Russell, A. J. 1995. A comparison of lipase catalyzed ester hydrolysis in reverse micelles, organic solvents, and biphasic systems. Biotechnol. Bioeng. 47: 60-70.
40. Zaks, A., Klibanov, A. M. 1988. Enzymatic catalysis in nonaqueous solvents. J. Biol. Chem. 263: 3194-3201.