Microbiological transformations 34: Enantioselective hydrolysis of a key-lactone involved in the synthesis of the antidepressant milnacipran®

Tetrahedron Letters

Volumn 37, Issue 26, 1996, Pages 4519-4522

  Viazzo, Pascale ^a   Alphand, Véronique ^a   Furstoss, Roland ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE; MILNACIPRAN;

ARTICLE; BACTERIUM TRANSFORMATION; BIOTRANSFORMATION; CATALYST; DRUG HYDROLYSIS; DRUG SCREENING; DRUG SYNTHESIS; ENANTIOMER; FUNGUS;

BACTERIA (MICROORGANISMS); BEAUVERIA; CUNNINGHAMELLA BLAKESLEEANA; FUNGI;

EID: 0030600158     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00872-6     Document Type: Article

References (24)

1. 1. a review: Benfield P., Heel R.C., Lewis S.P. Drugs, 1986, 32, 481-508
2. 2. Artigas F. CNS Drugs, 1995, 4, 79-89; Ansseau M., Papart P., Troisfontaines B., Bartholome F., Bataille M., Charles G., Schittecatte M., Darimont P., Devoitille J.M., Dewilde J., Dufrasne M. Gilson H., Evrard J.L., Denayer A., Kremer P., Mertens C., Serre C. Psychopharmacology, 1994, 114, 131-137.
3. 2. Artigas F. CNS Drugs, 1995, 4, 79-89; Ansseau M., Papart P., Troisfontaines B., Bartholome F., Bataille M., Charles G., Schittecatte M., Darimont P., Devoitille J.M., Dewilde J., Dufrasne M. Gilson H., Evrard J.L., Denayer A., Kremer P., Mertens C., Serre C. Psychopharmacology, 1994, 114, 131-137.
4. 3. Personal communication from the Pierre Fahre Médicament Society.
5. 4. For example, recent reviews: Boland W., Frossl C., Lorenz M. Synthesis, 1991, p. 1049-1072; Azerad R. Bull. Soc. Chim. Fr., 1995, 132, 17-51.
6. 4. For example, recent reviews: Boland W., Frossl C., Lorenz M. Synthesis, 1991, p. 1049-1072; Azerad R. Bull. Soc. Chim. Fr., 1995, 132, 17-51.
7. 5. Fishbein W.N., Bessman S.P. J. Biol. Chem., 1966, 241, 4835-4841 and 4842-4847.
8. 6. Blanco L., Guibé-Jampel E., Rousseau G., Tetrahedron Lett., 1988, 29, 1915-1918; Fouque E., Rousseau G. Synthesis, 1989, p.661-666.
9. 6. Blanco L., Guibé-Jampel E., Rousseau G., Tetrahedron Lett., 1988, 29, 1915-1918; Fouque E., Rousseau G. Synthesis, 1989, p.661-666.
10. 7. Guibé-Jampel E., Rousseau G., Blanco L. Tetrahedron Lett., 1989, 30, 67-68.
11. 8. Fellous R., Lizzani-Cuvelier L., Loiseau M.A., Sassy E. Tetrahedron: Asymmetry, 1994, 5, 343-346; Izumi T., Tamura F., Akutsu M. J. Heterocyclic Chem., 1994, 31, 441-445.
12. 8. Fellous R., Lizzani-Cuvelier L., Loiseau M.A., Sassy E. Tetrahedron: Asymmetry, 1994, 5, 343-346; Izumi T., Tamura F., Akutsu M. J. Heterocyclic Chem., 1994, 31, 441-445.
13. 9. Mori K. in "Total Synthesis of Natural Products", Wiley Interscience Publication, 1981, vol. 4.
14. 10. for example : He W., Pinard E., Paquette L.A. Helv. Chim. Acta., 1995, 78, 391-402; Martin S.F., Guinn D.E. Synthesis, 1991, 245-262.
15. 10. for example : He W., Pinard E., Paquette L.A. Helv. Chim. Acta., 1995, 78, 391-402; Martin S.F., Guinn D.E. Synthesis, 1991, 245-262.
16. 11. Griffin M., Trudgill P.W. Biochem. J., 1972, 129, 595-603; Eubanks E.F., Forney F.W., Larson D. J. Bacteriol., 1974, 120, 1133-1143; Schum A.C., Markovetz A.J. J. Bacteriol., 1974, 118, 890-897; Trower M.K., Buckland R.M., Higgins R., Griffin M. Appl. Environ. Microbiol., 1985, 49, 1282-1289; Bennett A.P., Strang E.J., Trudgill P.W., Wong V. J. Gen. Microbiol., 1988, 134, 161-168.
17. 11. Griffin M., Trudgill P.W. Biochem. J., 1972, 129, 595-603; Eubanks E.F., Forney F.W., Larson D. J. Bacteriol., 1974, 120, 1133-1143; Schum A.C., Markovetz A.J. J. Bacteriol., 1974, 118, 890-897; Trower M.K., Buckland R.M., Higgins R., Griffin M. Appl. Environ. Microbiol., 1985, 49, 1282-1289; Bennett A.P., Strang E.J., Trudgill P.W., Wong V. J. Gen. Microbiol., 1988, 134, 161-168.
18. 11. Griffin M., Trudgill P.W. Biochem. J., 1972, 129, 595-603; Eubanks E.F., Forney F.W., Larson D. J. Bacteriol., 1974, 120, 1133-1143; Schum A.C., Markovetz A.J. J. Bacteriol., 1974, 118, 890-897; Trower M.K., Buckland R.M., Higgins R., Griffin M. Appl. Environ. Microbiol., 1985, 49, 1282-1289; Bennett A.P., Strang E.J., Trudgill P.W., Wong V. J. Gen. Microbiol., 1988, 134, 161-168.
19. 11. Griffin M., Trudgill P.W. Biochem. J., 1972, 129, 595-603; Eubanks E.F., Forney F.W., Larson D. J. Bacteriol., 1974, 120, 1133-1143; Schum A.C., Markovetz A.J. J. Bacteriol., 1974, 118, 890-897; Trower M.K., Buckland R.M., Higgins R., Griffin M. Appl. Environ. Microbiol., 1985, 49, 1282-1289; Bennett A.P., Strang E.J., Trudgill P.W., Wong V. J. Gen. Microbiol., 1988, 134, 161-168.
20. 11. Griffin M., Trudgill P.W. Biochem. J., 1972, 129, 595-603; Eubanks E.F., Forney F.W., Larson D. J. Bacteriol., 1974, 120, 1133-1143; Schum A.C., Markovetz A.J. J. Bacteriol., 1974, 118, 890-897; Trower M.K., Buckland R.M., Higgins R., Griffin M. Appl. Environ. Microbiol., 1985, 49, 1282-1289; Bennett A.P., Strang E.J., Trudgill P.W., Wong V. J. Gen. Microbiol., 1988, 134, 161-168.
21. 12. Maruyama K. J. Biochem., 1983, 93, 557-565; Schlömann M., Ngai K.-L., Ornston N., Knackmuss H.-J. J. Bacteriol., 1993, 775, 2994-3001.
22. 12. Maruyama K. J. Biochem., 1983, 93, 557-565; Schlömann M., Ngai K.-L., Ornston N., Knackmuss H.-J. J. Bacteriol., 1993, 775, 2994-3001.
23. 13. Chen C.S., Fujimoto Y., Girdaukas G., Sih C.J. J. Am. Chem. Soc., 1982, 104, 7294.
24. 14. A very efficient chemical access to both enantiomers of milnacipran® has been published while we were finishing this work: see Shuto S., Ono S., Hase Y., Kamiyama N., Matsuda A. Tetrahedron Lett., 1996, 37, 641-644.