Increased racemate resolution of propranolol esters by lipase immobilized catalysis

Latin American Applied Research

Volumn 35, Issue 4, 2005, Pages 307-311

  Avila, R ^a   Ruiz, R ^a   Amaro Gonzalez D ^a   Diaz O ^a   Gonzalez J A ^a   Nunez A J ^a  

^a Center of Pharmaceutical Chemistry Cuba   (Cuba)

Author keywords

Biotransformation; Candida rugosa; Enantioselectivity; Lipase; Propranolol; Pseudomona fluorescens

Indexed keywords

EID: 27744576870     PISSN: 03270793     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (26)

1. Arroyo, M. and J.V. Sinisterra, "High Enantioselective Esterification of 2-Arylpropionic Acids Catalyzed by Immobilized Lipase from Candida antarctica: A Mechanistic Approach," J. Org. Chem, 59, 4410-4417 (1994).
2. Ávila-González R, Díaz O, Ruiz R, González JA. "Determinación de propranolol por cromatografía líquida de alta resolución," R. CENIC, Ciencias Químicas, 29, 147-149 (1997).
3. Barrett, A.M., "Cardiobeta-adrenoceptor blokade: the guest for selectivity," J Pharmacol. 2, 95-108 (1985).
4. Bastida, A., P. Sabuquillo, P. Armisen, R. Fernández-Lafuente, J. Huguet and J.M. Guisán, "A single step purification, inmobilization, and hyperactivation of lipases via interfacial adsorption on strongly hydrophobic supports," Biotechnology and bioengineering, 58, 486-493 (1998).
5. Bevinakatti, H.S. and A.A. Banerji, "Practical Chemoenzymatic synthesis of both enantiomers of propranolol," J Org Chem, 56, 5372-5375 (1991).
6. Chen, C.S., Y. Fujimoto, G. Girdaukas and C.J. Sih, "Quantitative analyses of biochemical kinetic resolutions of enantiomers," J Am Chem Soc 104, 7294-7299 (1982).
7. Chin-Shih Ch., Wakefield, R.I. Patent US 5,334,534 (1994).
8. Dordick, J.S., "Principles and applications of nonaqueous enzymology". In Blanch HW, Clark DS, editors. Applied biocatalysis, 1. New York: Marcel Dekker: 1-52 (1991).
9. Dordick, J.S., "Enzymatic catalysis in monophasic organic solvents," Enzyme Microb. Technol., 11, 194-211 (1989).
10. Fernández-Lorente, G., J.M. Palomo, C. Mateo, J.M. Guisán and R. Fernández-Lafuente, "Resolution of paroxetine precursor using different lipases influence of the reaction conditions on the enantioselectivity of lipases," Enzyme and Microbial Technology, 34, 264-269 (2004).
11. Goodman, L.S. and A. Gillman, The Pharmacological basis of therapeutics, Fourth Edition, MacMillan Company, New York. (1985).
12. Gatterman, L., Practices of Organic Chemistry, 2da Edición Española, 159-162 (1961).
13. Hermansson, J. and C. von Bahr, "Simultaneous determination of d- and 1-Propranolol in human plasma by high-performance liquid chromatography," J. Chromatogr, 221, 109-117 (1980).
14. Hermansson, J., "Separation and quantification of (R)- and (S)-Propranolol as their diastereomeric derivatives in human plasma by reversed-phase ion-pair chromatography," Acta Pharm Suec, 19, 11-24 (1982).
15. Himmelblau, D.M., Process Analysis by Statistical Methods, John Wiley & sons. New York (1970).
16. Howe, R. and R.G. Shanks, "Optical isomers of propranolol," Nature, 210, 1336-1368 (1966).
17. Khmelnitsky, Y.L. and J.O. Rich, "Biocatalysis in non organic solvents," Curr Opin Chem Biol, 3, 47-53 (1999).
18. Matsuo, N. and N. Ohno, "Preparation of optically active 1-acetoxy-2-aryloxypropionitriles and its application to a facile synthesis of (S)-(-)-Propranolol," Tetrahedron Lett, 26, 5533-5534 (1985).
19. Potter, L.T., "A radiometric microassay of acetylcholinesterase, " J Pharmacol Exp Ther, 156, 500-506 (1967).
20. Rahn, K.H., A. Hawlina, F. Kersting and G. Planz, "Studies on the antihypertensive action of the optical isomers of propranolol in man," Naunyn Schmiedebergs Arch Pharmacol, 286, 319-323 (1974)
21. Santaniello, E. P. Ferraboschi and P. Grisenti, "Lipase-catalyzed transesterification in organic solvents: applications to the preparation of enantiomerically pure compounds," Enzyme Microb Technol, 15, 367-382(1993).
22. Silber, B. and S. Riegelman, "Stereospecific assay for (-)- and (+)- propranolol in human and dog plasma," J Pharmacol Exp Ther, 215, 643-648 (1980).
23. Terao, Y., M. Murata, K. Achiwa, T. Nishino, M. Akamatsu and M. Kamimura, "Highly efficient lipase-catalysed asymmetric synthesis of chiral glicerol derivatives leading to practical synthesis of S-propranolol," Tetrahedron Lett, 29, 5173-5176 (1988).
24. Thompson, J.A., J.L. Holtzman, M. Tsuru and C.L. Lerman, "Procedure for the chiral derivatization and chromatographyc resolution of R-(+)- and S-(-)- propranolol," J Chromatogr, 238, 470-475 (1982).
25. Walle, T., U.K. Walle, M.J. Wilson, T.C. Fagan and T.E. Gaffney, "Stereoselective ring oxidation of propranolol in man," Br J Clin Pharmacol, 18, 741-748 (1984).
26. Yost, Y. and J.L. Holtzman, "Resolution of (+/-) Propranolol," J Pharm Sci, 16, 1181-1182 (1979).