Almond oxynitrilase-catalyzed transformation of aldehydes is strongly influenced by naphthyl and alkoxy substituents

Tetrahedron Asymmetry

Volumn 10, Issue 20, 1999, Pages 3939-3949

  Roda, Gabriella ^a,b   Riva, Sergio ^a   Danieli, Bruno ^b  

^a CNR   (Italy)

^b UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALKANE DERIVATIVE; NAPHTHYL GROUP; NITRILASE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; ENZYME SPECIFICITY; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0033462190     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00427-9     Document Type: Article

References (30)

1. Part 3. For Part 2, see: Danieli, B.; Frattini, S.; Roda, G.; Carrea, G.; Riva, S. J. Mol. Catal. B: Enzymatic 1998, 5, 223-228.
2. Henderson, I.; Wong, C.-H.; Effenberger, F. In Enzyme Catalysis in Organic Synthesis; Drauz, K.; Waldmann, H., Eds.; VCH: Weinheim, 1995; pp. 547-594.
3. For recent reviews, see: (a) Effenberger, F. Chimia 1999, 53, 3-10; (b) Griengl, H.; Hickel, A.; Johnson D. V.; Kratky, C.; Schmidt, M.; Schwab, H. Chem. Commun. 1997, 1933-1940.
4. For recent reviews, see: (a) Effenberger, F. Chimia 1999, 53, 3-10; (b) Griengl, H.; Hickel, A.; Johnson D. V.; Kratky, C.; Schmidt, M.; Schwab, H. Chem. Commun. 1997, 1933-1940.
5. (a) Carrea, G.; Riva, S. Angew. Chem., Int. Ed. Engl., in press;
6. (b) Riva, S. In Enzymatic Reactions in Organic Media; Koskinen, A. P. G.; Klibanov, A. M., Eds.; Blackie, A and P: London, 1995; pp. 140-169.
7. (c) Carrea, G.; Ottolina, S.; Riva, S. Trends Biotechnol. 1995, 13, 63-70.
8. (d) Danieli, B.; Riva, S. Pure Appl. Chem. 1994, 66, 2215-2218.
9. Danieli, B.; Barra, C.; Carrea, S.; Riva, S. Tetrahedron: Asymmetry 1996, 7, 1675-1682.
10. Mancuso, A. J.; Swern, D. Synthesis 1981, 165-185.
11. Leanna, M. R.; Sowin, T. J.; Morton, H. E. Tetrahedron Lett. 1992, 33, 5029-5032.
12. Inagaki, M.; Hiratake, J.; Nishioka, T.; Oda, J. J. Org. Chem. 1992, 57, 5643-5649.
13. Matsumoto, T.; Takeda, Y.; Iwata, E.; Sakamoto, M.; Ishida, T. Chem. Pharm. Bull. 1994, 42, 1191-1197.
14. Santaniello, E.; Ferraboschi, P.; Grisenti, P.; Manzocchi, A.; Trave, S. Gazz. Chim. Ital. 1989, 119, 581-584.
15. Kobayashi, Y.; Takase, M.; Ito, Y.; Terashima, S. Bull. Chem. Soc. Jpn. 1989, 62, 3038-3040.
16. Ognyanov, F.; Datcheva, V. K.; Kyler, K. S. J. Am. Chem. Soc. 1991, 113, 6992-6996.
17. Griengl, H.; Klempier, N.; Pöchlauer, P.; Schmidt, M.; Shi, N.; Zabelinskaja-Mackova, A. A. Tetrahedron 1998, 54, 14477-14486.
18. Hanefeld, U.; Straathof, A. J. J.; Heijnen, J. J. Biochim. Biophys. Acta 1999, 1432, 185-193.
19. Chiari, M.; Gelain, A.; Riva, S.; Tura, D. Electrophoresis 1997, 18, 2050-2054.
20. Kulasegaram, S.; Kulawiec, R. J. J. Org. Chem. 1997, 62, 6547-6561.
21. Nakamura, N.; Nojima, M.; Kusabayashi, S. J. Am. Chem. Soc. 1987, 109, 4969-4973.
22. Colombo, L.; Gennari, C.; Scolastico, C.; Guanti, G.; Narisano, E. J. Chem. Soc., Perkin Trans. 1 1981, 1278-1283.
23. (a) Yang, H. W.; Romo, D. J. Org. Chem. 1998, 63, 1344-1347.
24. (b) Enders, D.; Bhushan, V. Tetrahedron. Lett. 1998, 29, 2437-2440.
25. Buckley, T. F.; Rapoport, H. J. Am. Chem. Soc. 1982, 104, 4446-4450.
26. Yamaguchi, M.; Takata, T.; Endo, T. J. Org. Chem. 1990, 55, 1490-1492.
27. Moosavi, S. M.; Beddoes, R. S.; Watt, I. F. J. Chem. Soc., Perkin Trans. 2 1997, 1585-1596.
28. Walker, H. G.; Gee, M.; McCready, R. M. J. Org. Chem. 1962, 27, 2100-2102.
29. Bovara, R.; Carrea, G.; Ferrara, L.; Riva, S. Tetrahedron: Asymmetry 1991, 2, 931-938.
30. Carrea, G.; De Amici, M.; De Micheli, C.; Liverani, P.; Carnielli, M.; Riva, S. Tetrahedron: Asymmetry 1993, 4, 1063-1072.