On the stereochemistry of the Baker's Yeast-mediated reduction of regioisomeric unsaturated aldehydes: Examples of enantioselectivity switch promoted by substrate-engineering

Journal of Molecular Catalysis B: Enzymatic

Volumn 84, Issue , 2012, Pages 94-101

  Brenna, Elisabetta ^a   Fronza, Giovanni ^b   Fuganti, Claudio ^a   Gatti, Francesco G ^a   Manfredi, Alessia ^a   Parmeggiani, Fabio ^a   Ronchi, Paolo ^a  

^a POLITECNICO DI MILANO   (Italy)

^b CNR   (Italy)

Author keywords

Baker's Yeast; Deuterium NMR spectroscopy; Enantioselectivity; Reduction; Unsaturated aldehydes

Indexed keywords

BAKER'S YEAST; BIOREDUCTIONS; DEUTERIUM NMR SPECTROSCOPY; ENANTIOMERIC EXCESS; ENANTIOSELECTIVE REACTIONS; REGIOISOMERS; UNSATURATED ALDEHYDES;

ALDEHYDES; DEUTERIUM; ENANTIOMERS; EXPERIMENTS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC COMPOUNDS; REDUCTION; STEREOCHEMISTRY;

ENANTIOSELECTIVITY;

2 BENZYLACRYLALDEHYDE; 2 METHYLCINNAMALDEHYDE; ALDEHYDE; DEUTERIUM; PROTON; UNCLASSIFIED DRUG;

CHEMICAL STRUCTURE; CONFERENCE PAPER; ENANTIOSELECTIVITY; SACCHAROMYCES CEREVISIAE; STEREOCHEMISTRY; SYNTHESIS;

EID: 84866418107     PISSN: 13811177     EISSN: 18733158     Source Type: Journal    
DOI: 10.1016/j.molcatb.2012.02.003     Document Type: Conference Paper

References (38)

1. D. Seebach, and H.-O. Kalinowski Nachr. Chem. Tech. Lab. 24 1976 25
2. C. Fuganti Pure Appl. Chem. 62 1990 1449 1452
3. R. Csuk, and B.I. Glaenzer Chem. Rev. 91 1991 49 97
4. B. Pscheidt, and A. Glieder Microb. Cell Factories 7 2008 25
5. E. Brenna, F.G. Gatti, A. Manfredi, D. Monti, and F. Parmeggiani Org. Process Res. Dev. 16 2012 262 268
6. M. Bechtold, E. Brenna, C. Femmer, F.G. Gatti, S. Panke, F. Parmeggiani, and A. Sacchetti Org. Process Res. Dev. 16 2012 269 276
7. R. Bernardi, R. Cardillo, and D. Ghiringhelli J. Chem. Soc. Chem. Commun. 1984 460 461
8. G. Tuynenburg Muys, B. van der Ven, and A.P. de Jonge Nature 194 1962 995 996
9. H. Akita, A. Furuichi, H.K. Oshiji, K. Horikoshi, and T. Oishi Tetrahedron Lett. 23 1982 4051 4054
10. B. Wipf, E. Kupfer, R. Bertazzi, and H.G.W. Leuenberger Helv. Chim. Acta 66 1983 485 488
11. B. Zhou, A.S. Gopalan, F. VanMiddlesworth, W.-R. Shieh, and C. Sih J. Am. Chem. Soc. 105 1983 5925
12. M. Utaka, S. Konishi, A. Mizouka, T. Ohkubo, T. Sakai, S. Tsuboi, and A. Takeda J. Org. Chem. 54 1989 4989 4992
13. E. Brenna, G. Fronza, C. Fuganti, D. Monti, and F. Parmeggiani J. Mol. Cat. B: Enzym. 73 2011 17 21
14. M. Hall, C. Stueckler, B. Hauer, R. Stuermer, T. Friedrich, M. Breuer, W. Kroutil, and K. Faber Eur. J. Org. Chem. 2007 1511 1516
15. G. Fronza, C. Fuganti, and S. Serra Eur. J. Org. Chem 2009 6160 6171
16. C. Fuganti, P. Grasselli, and S. Servi J. Chem. Soc. Perkin Trans. I 1983 241 244
17. C. Fuganti, and P. Grasselli Chem. Ind. (Lond.) 1977 983
18. E. Brenna, F.G. Gatti, D. Monti, F. Parmeggiani, and A. Sacchetti Chem. Commun. 48 2012 79 81
19. J. Wrobel, J. Millen, J. Sredy, A. Dietrich, B.J. Gorham, M. Malamas, J.M. Kelly, J.G. Bauman, M.C. Harrison, L.R. Jones, C. Guinosso, and K. Sestanj J. Med. Chem. 34 1991 2504 2520
20. E. Brenna, F.G. Gatti, D. Monti, F. Parmeggiani, and S. Serra Adv. Synth. Catal. 354 2012 105 112
21. H. Simon, M. Kellner, and H. Guenther Angew. Chem. Int. Ed. 12 1973 146
22. C. Fuganti, D. Ghiringhelli, and P. Grasselli J. Chem. Soc. Chem. Commun. 1975 846 847
23. H. Gerlach, and B. Zagalak J. Chem. Soc. Chem. Commun. 1973 274 275
24. C. Fuganti, P. Grasselli, G. Poli, S. Servi, and A. Zorzella J. Chem. Soc. Chem. Commun. 1988 1619 1621
25. E.J. Corey, and G.N. Widiger J. Org. Chem. 40 1975 2975 2976
26. G. Fronza, C. Fuganti, P. Grasselli, G. Poli, and S. Servi J. Org. Chem. 53 1988 6153 6154
27. P. Ferraboschi, S. Reza-Elahi, E. Verza, and E. Santaniello Tetrahedron: Asymm. 10 1999 2639 2642
28. V. Šunjić, M. Majerić, and Z. Hamerŝak Croat. Chem. Acta 69 1996 643 660
29. H. Huschmann, W. Strassburger, E. Friderichs, EP 0693475 A1, 1996.
30. K. Biswas, C. Boerner, J. Gimeno, P.J. Goldsmith, D. Ramazzotti, A.L. So, and S. Woodward Tetrahedron 61 2005 1433 1442
31. X. Feng, Y.Q. Yuan, H.L. Cui, K. Jiang, and Y.C. Chen Org. Biomol. Chem. 7 2009 3660 3662
32. I. Shiina, Y. Yamai, and T. Shimazaki J. Org. Chem. 70 2005 8103 8106
33. B. Das, B.S. Ksanth, K.R. Reddy, G. Satyalakshmi, and R.A. Kumar Chem. Lett. 37 2008 512 513
34. A. Bouzide Org. Lett. 4 2002 1347 1350
35. J.C. Depezay, and Y. Le Merrer Tetrahedron Lett. 1974 2751 2754
36. R. Buchholtz, and H.M.R. Hoffmann Helv. Chim. Acta 74 1991 1213 1220
37. D. Basavaiah, and N. Kumaragurubaran Tetrahedron Lett. 42 2001 477 479
38. P.C. Hutchison, T.D. Heightman, and D.J. Procter J. Org. Chem. 69 2004 790 801