Enantioselective CC bond reduction of unsaturated α-chloro esters by old yellow enzymes

Journal of Molecular Catalysis B: Enzymatic

Volumn 73, Issue 1-4, 2011, Pages 17-21

  Brenna, Elisabetta ^a   Fronza, Giovanni ^b   Fuganti, Claudio ^a   Monti, Daniela ^b   Parmeggiani, Fabio ^a  

^a POLITECNICO DI MILANO   (Italy)

^b CNR   (Italy)

Author keywords

Deuterium NMR; Enantioselective reduction; Enoate reductase; Old yellow enzymes

Indexed keywords

BAKER'S YEAST; C-C BONDS; C-C DOUBLE BONDS; DEUTERIUM LABELING; DEUTERIUM NMR; ENANTIOSELECTIVE; ENANTIOSELECTIVE REDUCTION; ENOATE REDUCTASE; HYDROGEN ADDITION; OLD YELLOW ENZYMES; WHOLE CELL;

DEUTERIUM; ENANTIOSELECTIVITY; ENZYME ACTIVITY; ESTERS; HYDROGEN; STEREOCHEMISTRY;

ESTERIFICATION;

2 ENOATE REDUCTASE; ALPHA CHLORO ESTER DERIVATIVE; DEUTERIUM; ESTER DERIVATIVE; HYDROGEN; METHYL 2 CHLORO 4 METHYLPENT 2 ENOATE; METHYL 2,4,4 TRICHLOROBUT 2 ENOATE; METHYL 2,4,4,4 TETRACHLOROBUT 2 ENOATE; OXIDOREDUCTASE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; BIOTRANSFORMATION; CHEMICAL BOND; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; ENZYME SUBSTRATE; NONHUMAN; REDUCTION; SACCHAROMYCES CEREVISIAE; STEREOCHEMISTRY;

EID: 80052966037     PISSN: 13811177     EISSN: 18733158     Source Type: Journal    
DOI: 10.1016/j.molcatb.2011.07.008     Document Type: Article

References (25)

1. C. Fuganti Pure Appl. Chem. 62 1990 1449 1452
2. C. Fuganti, P. Grasselli, Baker's yeast-mediated synthesis of natural products in biocatalysis, in: Agricultural Biotechnology, Chapter 25, ACS Symposium Series, vol. 389, American Chemical Society, Washington, 1989, pp. 359-370.
3. S. Servi Synthesis 1990 1 25
4. R. Csuk, and B.I. Glänzer Chem. Rev. 91 1991 49 97
5. K. Faber Biotransformations in Organic Chemistry 2004 Springer-Verlag Berlin/Heidelberg Chapter 2.2, pp. 177-212
6. R. Stuermer, B. Hauer, M. Hall, and K. Faber Curr. Opin. Chem. Biol. 11 2007 203 213
7. M. Utaka, S. Konishi, T. Ohkubo, S. Tsuboi, and A. Takeda Tetrahedron Lett. 28 1987 1447 1449
8. M. Utaka, S. Konishi, A. Mizouka, T. Ohkubo, T. Sakai, S. Tsuboi, and A. Takeda J. Org. Chem. 54 1989 4989 4992
9. R.E. Williams, and N.C. Bruce Microbiology 148 2002 1607 1614
10. M. Hall, C. Stueckler, B. Hauer, R. Stuermer, T. Friedrich, M. Breuer, W. Kroutil, and K. Faber Eur. J. Org. Chem. 2008 1511 1516
11. H. Toogood, J.M. Gardiner, and N.S. Scrutton ChemCatChem 2 2010 892 914
12. C. Stueckler, C.K. Winkler, M. Bonnekessel, and K. Faber Adv. Synth. Catal. 352 2010 2663 2666
13. C. Stueckler, C.K. Winkler, M. Hall, B. Hauer, M. Bonnekessel, K. Zangger, and K. Faber Adv. Synth. Catal. 353 2011 1169 1173
14. K. Saito, D.J. Thiele, M. Davio, O. Lockridge, and V. Massey J. Biol. Chem. 266 1991 20720 20724
15. K. Stott, K. Saito, D.J. Thiele, and V. Massey J. Biol. Chem. 268 1993 6097 6106
16. Y.S. Niino, S. Chakraborty, B.J. Brown, and V. Massey J. Biol. Chem. 270 1995 1983 1991
17. S. Tsuboi, T. Uno, and A. Takeda Chem. Lett. 1978 1325 1328
18. R.E. Williams, D.A. Rathborne, N.S. Scrutton, and N.C. Bruce Appl. Environ. Microbiol. 70 2004 3566 3574
19. M. Bechtold, E. Brenna, C. Femmer, F.G. Gatti, S. Panke, F. Parmeggiani, A. Sacchetti, Org. Proc. Res. Dev. (in press).
20. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople Gaussian 03, Revision B. 04 2004 Gaussian, Inc. Wallingford, CT
21. R.G. Parr, and W. Yang Density Functional Theory of Atoms and Molecules 1989 Oxford Scientific
22. W. Koch, and M.C. Holthausen A Chemist's Guide to Density Functional Theory 2001 Wiley VCH
23. F. Jensen Introduction to Computational Chemistry 2007 Wiley and Sons Chichester
24. E. Brenna, F.G. Gatti, A. Manfredi, D. Monti, F. Parmeggiani, Eur. J. Org. Chem. (2011), 4015-4022.
25. E. Brenna, F.G. Gatti, A. Manfredi, D. Monti, F. Parmeggiani, Org. Proc. Res. Dev. (in press).