Oxynitrilase-catalyzed transformation of substituted aldehydes: The case of (±)-2-phenylpropionaldehyde and of (±)-3-phenylbutyraldehyde

Tetrahedron Asymmetry

Volumn 7, Issue 6, 1996, Pages 1675-1682

  Danieli, Bruno ^a   Barra, Carlo ^a   Carrea, Giacomo ^b   Riva, Sergio ^b  

^a UNIVERSITY OF MILAN   (Italy)

^b CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALDEHYDE DERIVATIVE; ARYLBUTYRIC ACID DERIVATIVE; HYDRATROPIC ACID DERIVATIVE; NITRILASE;

ARTICLE; CATALYSIS; ENZYME MECHANISM; ENZYME SUBSTRATE; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0029882690     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00201-7     Document Type: Article

References (23)

1. For recent reviews see: a) Wong, C.H.; Whitesides, G.M. 'Enzymes in Synthetic Orgainc Chemistry', Pergamon Publishers: Trowbridge (U.K.). 1994; pp 195-251.
2. b) Drauz, K.; Waldmann, H. 'Enzyme Catalysis in Organic Synthesis', VCH Publishers: Weinheim (Germany). 1995; pp. 547-593.
3. For a recent review see: Effenberger, F. Angew.Chem.Int.Ed.Engl., 1994, 33, 1555.
4. a) Danieli, B.; Luisetti, M.; Riva, S.; Bertinotti, A.; Ragg, E.; Scaglioni, L.; Bombardelli, E. J.Org.Chem., 1995, 60, 3637.
5. b) Carrea, G.; Ottolina, G.; Riva, S. TIBTECH, 1995, 13, 63.
6. c) Danieli, B.; Riva, S. Pure & Applied Chem. 1994, 66, 2215.
7. Rosenthaler, R. Biochem. Z., 1908, 14, 238.
8. Smitskamp-Wilms, E.; Brussee, J.; Van der Gentile, A.; Van der Schanemburg, G.J.M., Sloothaok, J.B. Recl.Trav.Chim. Pays-Bas 1991, 110, 209.
9. a) Effenberger, F.; Ziegler, T.; Forster, S. Angew Chem.Int.Ed.Eng. 1987, 26, 458.
10. b) Brussee, J.; Loos, W.T.; Kruse, C.G.; van der Gentile, A. Tetrahedron 1990, 46, 979.
11. c) Huuhtanen, T.T.; Kanerva, L.T. Tetrahedron:Asymmetry 1992, 3, 1223.
12. d) Menendez, E.; Brieva, R.; Rebolledo, F.; Gotor, V. J.Chem.Soc.Chem.Commun. 1995, 989.
13. Ognyanov, F.; Datcheva, V.K.; Kyler, K.S. J.Am.Chem.Soc. 1991, 113, 6992.
14. Effenberger, F.; Eichhorn, J.; Roos, J. Tetrahedron:Asymmetry 1995, 6, 271.
15. This methodology was chosen among the different protocols found in the literature because of the minimal spontaneous chemical reaction of the in situ generated HCN with our substrate.
16. Separation was achieved only on analytical scale. Attempts to reproduce this purification procedure with preparative HPLC were unsuccessfull due to solubility problems.
17. a) Inagaki, M.; Hatanaka, A.; Mimura, M.; Hiratake, J.; Nishioka, T.; Oda, J. Bull.Chem.Soc.Jpn. 1992, 65, 111.
18. b) Effenberger, F.; Gutterer, B.; Ziegler, T.; Aichholz, R. Liebigs Ann.Chem. 1991, 47.
19. a) Weissfloch, A.N.E.; Kazlauskas, R.J. J.Org.Chem., 1995, 60, 6959.
20. b) Kazlauskas, K.J.; Weissfloch, A.N.E.; Rappaport, A.T.; Cuccia, L.A. J.Org.Chem., 1991, 56, 2656.
21. Akita, H.; Fumichi, A.; Koshiji, H.; Horitoshi, K.; Oishi, T. Chem.Pharm.Bull., 1984, 32, 1324.
22. Lauble, H.; Muller, K.; Schindelin, H.; Forster, S.; Effenberger, F. Proteins: Struct.Funct.Genet, 1994, 79, 343.
23. Secundo, F.; Riva, S.; Carrea, G. Tetrahedron:Asymmetry, 1992, 3, 267.