Stereochemical analysis of the enzymic reduction of the double bond of α- and β-substituted nitrostyrenes and α-ethoxycinnamaldehyde through deuterium labelling experiments

European Journal of Organic Chemistry

Volumn , Issue 26, 2010, Pages 5077-5084

  Brenna, Elisabetta ^a   Fronza, Giovanni ^b   Fuganti, Claudio ^a   Gatti, Francesco G ^a  

^a POLITECNICO DI MILANO   (Italy)

^b CNR   (Italy)

Author keywords

Enzyme catalysis; Isotopic labeling; Reduction

Indexed keywords

EID: 77956391619     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201000442     Document Type: Article

References (27)

1. C. Fuganti, P. Grasselli, Chem. Ind. (London) 1977, 983.
2. C. Fuganti, D. Ghiringhelli, P. Grasselli, J. Chem. Soc., Chem. Commun. 1975, 846-847.
3. G. Fronza, C. Fuganti, M. Pinciroli, S. Serra, Tetrahedron: Asymmetry 2004, 53, 9383-9388.
4. G. Fronza, C. Fuganti, P. Grasselli, A. Mele, J. Org. Chem. 1991, 56, 6019-6023.
5. G. Fronza, C. Fuganti, P. Grasselli, S. Lanati, R. Rallo, S. Tchilibon, J. Chem. Soc. Perkin Trans. 1 1994, 2927-2930.
6. G. Fogliato, G. Fronza, C. Fuganti, S. Lanati, R. Rallo, R. Rigoni, S. Servi, Tetrahedron 1995, 51, 10231-10240.
7. G. Fronza, C. Fuganti, M. Mendozza, R. Rallo, G. Ottolina, D. Joulain, Tetrahedron 1996, 52, 4041-4052.
8. G. Fronza, C. Fuganti, P. Grasselli, M. Barbeni, Tetrahedron Lett. 1992, 33, 6375-6378.
9. G. Fronza, C. Fuganti, P. Grasselli, A. Mele, A. Sarra, G. Allegrone, M. Barbeni, Tetrahedron Lett. 1993, 34, 6467-6470.
10. H. Simon, M. Kellner, H. Guenther, Angew. Chem. Int. Ed. Engl. 1973, 12, 146-147.
11. D. J. Bougioukou, J. D. Stewart, J. Am. Chem. Soc. 2008, 130, 7655-7658.
12. M. Hall, C. Stueckler, H. Ehammer, E. Pointner, G. Oberdorfer, K. Gruber, B. Hauer, R. Stuermer, W. Kroutil, P. Macheroux, K. Faber, Adv. Synth. Catal. 2008, 350, 411-418.
13. R. Stuermer, B. Hauer, M. Hall, K. Faber, Curr. Opin. Chem. Biol. 2007, 11, 213-213
14. Y. Kawai, Y. Inaba, N. Tokitoh, Tetrahedron: Asymmetry 2001, 12, 309-318.
15. G. Fronza, C. Fuganti, S. Serra, Eur. J. Org. Chem. 2009, 6160-6171.
16. H. S. Toogood, A. Fryszkowska, V. Hare, K. Fisher, A. Roujeinikova, D. Leys, J. M. Gardiner, G. M. Stephens, N. S. Scrutton, Adv. Synth. Catal. 2008, 350, 2789-2803
17. BY reduction of other nitrostyrenes: H. Ohta, K. Ozaki, G.-I.-Tsuchihashi, Chem. Lett. 1987, 191
18. H. Ohta, N. Kobayashi, K. Ozaki, J. Org. Chem. 1989, 54, 1802-1804.
19. A. Fryszkowska, K. Fisher, J. M. Gardiner, G. M. Stephens, J. Org. Chem. 2008, 73, 4295-4298.
20. N. Rastogi, I. N. N. Namboothiri, M. Cojocaru, Tetrahedron Lett. 2004, 45, 4745-4748.
21. E. Brenna, C. Fuganti, F. G. Gatti, F. Parmeggiani, Tetrahedron: Asymmetry, in press.
22. F. W. Hoover, H. B. Hass, J. Org. Chem. 1947, 12, 506-509.
23. M. Abarbri, A. Guignard, M. Lamant, Helv. Chim. Acta 1995, 78, 109-121.
24. Y. Meah, V. Massey, Proc. Natl. Acad. Sci. USA 2000, 97, 10733-10735.
25. A. D. N. Vaz, S. Chakraborty, V. Massey, Biochemistry 1995, 34, 4246-4256.
26. E. Erlenmeyer, Justus Liebigs Ann. Chem. 1893, 275, 1-8.
27. M. Cutolo, V. Fiandanese, F. Naso, O. Sciacovelli, Tetrahedron Lett. 1983, 24, 4603-4606.