Asymmetric bioreductions of β-nitro acrylates as a route to chiral β2-amino acids

Organic Letters

Volumn 8, Issue 26, 2006, Pages 6131-6133

  Swiderska, Magdalena A ^a   Stewart, Jon D ^a  

^a University of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID; ACRYLIC ACID DERIVATIVE; AMINO ACID;

ARTICLE; CHEMISTRY; OXIDATION REDUCTION REACTION;

ACRYLATES; AMINO ACIDS; OXIDATION-REDUCTION;

EID: 33846160588     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062612f     Document Type: Article

References (39)

1. Lee, H.-S.; Park, J.-S.; Kim, B. M.; Gellman, S. H. J. Org. Chem. 2003, 68, 1575-1578.
2. (a) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 117-128.
3. (b) Sewald, N. Angew. Chem., Int. Ed. 2003, 42, 5794-5795.
4. (c) Lelais, G.; Seebach, D. Biopolymers 2004, 76, 206-243.
5. (a) Sibi, M. P.; Patil, K. Angew. Chem., Int. Ed. 2004, 43, 1235-1238.
6. (b) Sibi, M. P.; Tatamidani, H.; Patil, K. Org. Lett. 2005, 7, 2571-2573.
7. (c) Sibi, M. P.; Patil, K. Tetrahedron: Asymmetry 2006, 17, 516-519.
8. (a) Eilitz, U.; Lessmann, F.; Seidelmann, O.; Wendisch, V. Tetrahedron: Asymmetry 2003, 14, 189-191.
9. (b) Eilitz, U.; Lessmann, F.; Seidelmann, O.; Wendisch, V. Tetrahedron: Asymmetry 2003, 14, 3095-3097.
10. (c) Rimkus, A.; Sewald, N. Org. Lett. 2003, 5, 79-80.
11. Saylik, D.; Campi, E. M.; Donohue, A. C.; Jackson, W. R.; Robinson, A. J. Tetrahedron: Asymmetry 2001, 12, 657-667.
12. Elaridi, J.; Thaqi, A.; Prosser, A.; Jackson, W. R.; Robinson, A. J. Tetrahedron: Asymmetry 2005, 16, 1309-1319.
13. Huang, H.; Liu, X.; Deng, J.; Qiu, M.; Zheng, Z. Org. Lett. 2006, 8, 3359-3362.
14. Swiderska, M. A.; Stewart, J. D. J. Mol. Catal. B: Enzym. 2006, 42, 52-54.
15. Kataoka, M.; Kotaka, A.; Hasegawa, A.; Wada, M.; Yoshizumi, a.; Nakamori, S.; Shimizu, S. Biosci. Biotechnol. Biochem. 2002, 66, 2651-2657.
16. Wada, M.; Yoshizumi, A.; Noda, Y.; Kataoka, M.; Shimizu, S.; Takagi, H.; Nakamori, S. Appl. Environ. Microbiol. 2003, 69, 933-937.
17. Müller, A.; Hauer, B.; Rosche, B. J. Mol. Catal. B: Enzym. 2006, 38, 126-130.
18. Macritchie, J. A.; Silcock, A.; Willis, C. L. Tetrahedron: Asymmetry 1997, 8, 3895-3902.
19. (a) Ballini, R.; Fiorini, D.; Palmieri, A. Tetrahedron Lett. 2004, 7027-7029.
20. (b) Palacios, F.; de los Santos, J.; Aparacio, D. ARKIVOC 2005, 405-414.
21. (c) Du, D.-M.; Lu, S.-F.; Fang, T.; Xu, J. J. Org. Chem. 2005, 70, 3712-3715.
22. (d) Li, H.; Wang, B.; Deng, L. J. Am. Chem. Soc. 2006, 128, 732-733.
23. 3) δ 173.1, 80.3, 77.7, 63.1, 34.3, 17.0, 16.4, 14.2.
24. Melton, J.; McMurry, J. E. J. Org. Chem. 1975, 40, 2138-2139.
25. Olefin configurations for 3c-g were assigned based on the chemical shift values of the allylic protons, e.g., 2.11 ppm for (Z)-3c versus 2.60 ppm for the methyl ester of (E)-3c (ref 15a), as described by Denmark and Marcin (J. Org. Chem. 1993, 58, 3850-3856.).
26. Abramovitz, A. S.; Massey, V. J. Biol. Chem. 1976, 251, 5321-5326.
27. 4, and concentrated in vacuo.
28. 2-amino acids as hydrochloride salts. Spectral data matched those reported previously: Nejman, M.; Sliwinska, A.; Zwierzak, A. Tetrahedron 2005, 61, 8536-8541.
29. Gangadhar, N.; Huber, V. J.; Lum, C.; Goodman, B. A. Org. Lett. 2000, 2, 3527-3529.
30. Sammis, G. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 4442-4443.
31. Lee, H. S.; Park, J. D.; Kim, D. H. Bull. Korean Chem. Soc. 2003, 24, 467-472.
32. (a) Kohli, R. M.; Massey, V. J. Biol. Chem. 1998, 273, 32763-32770.
33. (b) Xu, D.; Kohli, R. M.; Massey, V. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 3556-3561.
34. (c) Brown, B. J.; Hyun, J. w.; Duvvuri, S.; Karplus, P. A.; Massey, V. J. Biol. Chem. 2002, 277, 2138-2145.
35. (d) Fox, K. M.; Karplus, P. A. Structure 1994, 2, 1089-1105.
36. In a preliminary experiment, E-3d was reduced by old yellow enzyme with largely (S)-stereoselectivity, as would be expected from the model in Scheme 2. This suggests that it may be possible to prepare the enantiomeric series of β-amino acids by using the alternate olefin isomers.
37. The three byproducts were identified by GC/MS as (E)-3d, the alternate acrylate alkene regioisomer of 3d, and the water addition product from 3d (in racemic form).
38. Kawai, Y.; Inaba, Y.; Tokitoh, N. Tetrahedron: Asymmetry 2001, 12, 309-318.
39. Meah, Y.; Massey, V. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 10733-10738.