Microbiological transformations 37. An enantioconvergent synthesis of the β-blocker (R)-Nifenalol® using a combined chemoenzymatic approach

Tetrahedron

Volumn 53, Issue 28, 1997, Pages 9707-9714

  Pedragosa Moreau, S ^a   Morisseau, C ^a   Baratti, J ^a   Zylber, J ^a   Archelas, A ^a   Furstoss, R ^a  

^a ETABLISSEMENT FRANÇAIS DU SANG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BETA ADRENERGIC RECEPTOR BLOCKING AGENT; INDUSTRIAL CHEMICAL; NIFENALOL;

ARTICLE; CATALYSIS; CHIRALITY; ENANTIOMER; ENZYME ACTIVITY; HYDROLYSIS; HYDROXYLATION; MATHEMATICAL MODEL; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0030848933     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00639-X     Document Type: Article

References (24)

1. Katsuki, T. Coord. Chem. Rev. 1995, 140, 189-214
2. Jacobsen, E.S.; Kakiuchi, F.; Fonsler, R.G.; Larrow, J.F.; Tokunaga, M. Tetrahedron Lett. 1997, 38, 773-776.
3. Kolb, H.C.; van Nieuwenhze, M.S.; Sharpless, K.B. Chem. Rev. 1994, 94, 2483-22547
4. Pedragosa-Moreau, S.; Archelas, A.; Furstoss, R. Bull. Chem. Soc. Fr. 1995, 132, 769-800
5. Besse, P.; Veschambre, H. Tetrahedron 1994, 50, 8885-8927
6. Pedragosa-Moreau, S.; Archelas, A.; Furstoss, R. Tetrahedron 1996, 52, 4593-4606
7. Bellucci, G.; Chiappe, C.; Cordoni, A. Tetrahedron: Asymmetry 1996, 7, 197-202
8. Wixtrom, R.N.; Hammock, B.D. In: Biochemical pharmacology and toxicology, 1985, eds. D. Zakim, D.A. Vessey, 1:1-93. New York: Wiley
9. Tseng, H.F.; Laughlin, L.T; Lin, S; Armstrong, R.N. J. Am. Chem. Soc. 1996, 118, 9436-9437
10. Borhan, B.; Jones, A.D.; Pinot, F.; Grant, D.F.; Kurth, M.J.; Hammock, B.D. J. Biol. Chem. 1995, 270, 26923-26930
11. Blee, E.; Schuber, F. Eur. J. Biochem. 1995, 230, 229-234
12. Faber, K.; Mischitz, M.; Kroutil, W. Acta Chem. Scand. 1996, 50, 249-258
13. Chen, X.-J.; Archelas, A.; Furstoss, R. J. Org. Chem. 1993, 58, 5528-5532
14. Pedragosa-Moreau, S.; Archelas, A.; Furstoss, R. J. Org. Chem. 1993, 58, 5533-5536
15. Pedragosa-Moreau, S.; Archelas, A.; Furstoss, R. Bioorg. Med. Chem. 1994, 2, 609-616
16. Murmann, W.; Rumore, G.; Gamba, A. Bull. Chim. Farm. 1967, 106, 251-268
17. Almirante, L.; Murmann, W. J. Med. Chem. 1966, 9, 650-653
18. Pedragosa-Moreau, S.; Morisseau, C.; Zylber, J.; Archelas, A; Baratti, J.C.; Furstoss, R. J. Org. Chem. 1996, 61, 7402-7407
19. Vänttinen, E.; Kanerva, L.T. Tetrahedron: Asymmetry 1995, 6, 1779-1786
20. Chen, C.S.; Fujimoto, Y.; Girdaukas, G.; Sih, C.J. J. Am. Chem. Soc. 1982, 104, 7294-7298
21. Morisseau, C.; Nellaiah, H.; Archelas, A.; Furstoss, R.; Baratti, J.C. Enzyme Microb. Technol. 1997, 20, 446-452
22. 1 enzymatic unit (U) allows to transform 1 μmole/min of substrate.
23. Golding, B.T.; Hall, D.R.; Sakrikar, S.J. J. Chem. Soc., Perkin trans. 1 1973, 1, 1214-1220
24. Teotino, U.M.; Polo Friz, L.; Steis, G.; Della Bella, D. Il Farmaco - Ed. Sc. 1962, 17, 252-265