Kinetic resolution of a diltiazem intermediate by lipase-catalyzed enantioselective alcoholysis

Journal of Molecular Catalysis - B Enzymatic

Volumn 9, Issue 4-6, 2000, Pages 251-257

  Shapira Levinger, Michal ^a   Fishman, Ayelet ^a  

^a TAMI (IMI) Institute for Research and Development   (Israel)

Author keywords

Alcoholysis; Diltiazem; Lipases; Porcine liver acetone powder; Resolution

Indexed keywords

ALCOHOL DERIVATIVE; DILTIAZEM;

ARTICLE; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS; ENANTIOMER; ESTERIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; RECYCLING; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0034697073     PISSN: 13811177     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1381-1177(99)00102-2     Document Type: Article

References (36)

1. Patel R.N. Adv. Appl. Microbiol. 43:1997;91.
2. Gutman A.L., Shapira M. Adv. Biochem. Eng. Biotech. 52:1995;87.
3. Faber K., Franssen M. TIBTECH. 11:1993;461.
4. Santaniello E., Ferraboschi P., Grisenti P., Manzocchi A. Chem. Rev. 92:1992;1071.
5. Boland W., Frobl C., Lorenz M. Synthesis. 1991;1049.
6. Jones J.B. Tetrahedron. 42:1986;3351.
7. Whitesides G.M., Wong C.-H. Angew. Chem., Int. Ed. Engl. 24:1985;617.
8. Faber K., Riva S. Synthesis. 1992;895.
9. Xie Z.-F. Tetrahedron: Asymmetry. 2:1991;733.
10. Margolin A.L. CHEMTECH. 1991;160.
11. Klibanov A.M. Acc. Chem. Res. 23:1990;114.
12. Dordick J.S. Enzyme Microb. Technol. 11:1989;194.
13. Chen C.-S., Sih C.J. Angew. Chem., Int. Ed. Engl. 28:1989;695.
14. Godfraind T., Miller R., Wibo M. Pharm. Rev. 38:1986;321.
15. M. Villa, C. Pozzoli, Proc. Int. Symp. Chiral USA, Boston, 15-16 May 1995, paper no. 3.
16. Yamada S., Mori Y., Morimatsu K., Ishizu Y., Ozaki Y., Yoshioka R., Nakatani T., Seko H. J. Org. Chem. 61:1996;8586.
17. Lopez J.L., Matson S.L. J. Membrane Sci. 125:1997;189.
18. Matsumae H., Shibatani T. J. Ferment. Bioeng. 77:1994;152.
19. D.R. Dodds, J.L. Lopez, US Patent 5,2274,300, 1993.
20. Matsumae H., Furui M., Shibatani T. J. Ferment. Bioeng. 75:1993;93.
21. Laffitte J.A., Gancet C., Soccol C. Ind. J. Chem. 1993;94.
22. J.G.T. Kierkels, W.P.H. Peeters, EP Patent 602740, 1993.
23. Gentile A., Giordano C. J. Org. Chem. 57:1992;6635.
24. L.A. Hulshof, J.H. Roskam, EP Patent 343714, 1989.
25. Inoue H., Konda M., Hashiyama T., Otsuka H., Takahashi K., Gaino M., Date T., Aoe K., Takeda M., Murata S., Narita H., Nagao T. J. Med. Chem. 34:1991;675.
26. Senuma M., Shibazaki M., Nishimoto S., Shibata K., Okamura K., Date T. Chem. Phar. Bull. 37:1989;3204.
27. Akita H., Umezawa I., Matsukura H. Chem. Pharm. Bull. 45:1997;272.
28. Kanerva L.T., Sundholm O. J. Chem. Soc. Perkin Trans. 1:1993;2407.
29. Kanerva L.T., Sundholm O. J. Chem. Soc. Perkin Trans. 1:1993;1385.
30. Tanabe Seiyaku, Jpn. Patent JP 59 20,273 (1984).
31. Sakurai T., Margolin A.L., Russell A.J., Klibanov A.M. J. Am. Chem. Soc. 110:1988;7236.
32. Kitaguchi H., Fitzpatrick P.A., Huber J.E., Klibanov A.M. J. Am. Chem. Soc. 111:1989;3094.
33. Gutman A.L., Shkolnik E., Shapira M. Tetrahedron. 48:1992;8775.
34. Shkolnik E., Gutman A.L. Bioorg. Med. Cem. 2:1994;567.
35. Kim M.G., Lee S.B. J. Mol. Cat. B: Enzymatic. 2:1996;127.
36. Morimoto M., Kohno H., Yasuda K., Date T., Takamura N., Sugasawa S. Heterocycles. 30:1990;471.