Dehydro-β-amino acid containing peptides as promising sequences for drug development

European Journal of Organic Chemistry

Volumn , Issue 34, 2009, Pages 5991-5997

  Cardillo, Giuliana ^a   Gennari, Arianna ^a   Gentilucci, Luca ^a   Mosconi, Elisa ^a   Tolomelli, Alessandra ^a   Troisi, Stefano ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Amino acids; Chemo selectivity; Chiral resolution; Enzymes; Peptid omimetics; Regioselectivity

Indexed keywords

EID: 70749119425     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900870     Document Type: Article

References (38)

1. a) S. Hanessian, G. McNaughton-Smith, H. G. Lombart, W D. Lubell, Tetrahedron 1997, 53, 12789-12854;
2. b) J. Gante, Angew. Chem. Int. Ed. Engl 1994, 33, 1699-1720;
3. c) S. E. Gibson, N. Guillo, M. J. Tozer, Tetrahedron 1999, 55, 585-615;
4. d) C. Balsamini, E. Duranti, L. Mariani, A. Salvatori, G. Spadoni, Synthesis 1990, 779-781;
5. e) A. M. Yim, Y. Vidal, P. Viallefont, J. Martinez, Tetrahedron: Asymmetry 2002, 13, 503-510;
6. f) G. Cardillo, L. Gentilucci, A. Tolomelli, Mini-Rev. Med. Chem. 2006, 6, 293-304.
7. V. Farina, J. T. Reeves, C. H. Senanayake, J. J. Song, Chem. Rev. 2006, 106, 2734-2793.
8. For extensive reviews on β-amino acids, see: a) G. Cardillo, C. Tomasini, Chem. Soc Rev. 1996, 25, 117-128;
9. b) E. Juaristi (Ed.), Enantbselective Synthesis of β-Amino Acids, 1st ed., Wiley-VCH, New York, 1997;
10. c) E. Juaristi, V. A. Soloshonok (Eds.), Enantioselective Synthesis of β-Amino Acids, 2nd ed., Wiley, New York, 2005;
11. d) N. Sewald Angew. Chem. Int. Ed. 2003, 42, 5794-5795; for dehydro-ß-amino acids:
12. e) J. E. Baldwin, M. G. Moloney, M. North, J. Chem. Soc Perkin Trans. 1 1989, 833-834;
13. f) R. Buchhol, R. M. H. Hoffmann, Helv. Chim. Acta 1991, 74, 1213-1220;
14. g) B. Gardner, H. Nakanishi, M. Kahn, Tetrahedron 1993, 49, 3433-3448;
15. h) S. Rajesh, B. Banerji, J. Iqbal, J. Org. Chem. 2002, 67, 7852-7857;
16. i) S. Rajesh, S. Jyoti, B. Banerji, J. Iqbal, Ind. J. Chem. 2001, 40B, 1029-1032;
17. j) M. Paira,' S. K. Mandai, S. C. Roy, Tetrahedron Lett. 2008, 49, 2432-2434.
18. a) A. Giannis, T. Kolter, Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267;
19. b) A. Abell (Ed.), Advances in Amino Acid Mi-metics and Peptidomimetics, JAI Press, Greenwich, 1997, vol.1;
20. c) E. Benedetti, C. Pedone, M. Saviano in Frontiers in Drug Design and Discovery, Bentham Science, Sharjah, U.A.E., 2007, vol.3, pp. 539-558;
21. d) E. Clynen, G. Baggerman, S. J. Husson, B. Landuyt, L. Schoofs, Exp. Opin. Drug Disc 2008, 3, 425-440.
22. a) L. Gentilucci, G. Cardillo, A. Tolomelli, R. De Marco, A. Garelli, S. Spampinato, A. Spartà, E. Juaristi, ChemMedChem 2009, 4, 517-523;
23. b) L. Gentilucci, G. Cardillo, A. Tolomelli, S. Spampinato, A. Sparta, F. Squassabia, Eur. J. Org. Chem. 2008, 4, 729-735;
24. c) F. Benfatti, G. Cardillo, S. Fabbroni, P. Galzerano, L. Gentilucci, R. Juris, A. Tolomelli, M. Baiula, A. Spartà, S. Spampinato, Bioorg. Med. Chem. 2007, 15, 7380-7390;
25. d) L. Gentilucci, G. Cardillo, F. Squassabia, A. Tolomelli, S. Spampinato, A. Sparta, M. Baiula, Bioorg. Med. Chem. Lett, 2007,17, 2329-2333;
26. e) F. Benfatti, G. Cardillo, S. Fabbroni, L. Gentilucci, R. Perciaccante, A. Tolomelli, M. Baiula, S. Spampinato, Tetrahedron: Asymmetry 2006, 17, 167-170.
27. a) R. O. Hynes, Cell 1992, 69, 11-25;
28. b) G. P. Curley, H. Blum, M. J. Humphries, Cell Mol Life Sci. 1999, 56, 427-441;
29. c) K.-E. Gottschalk, H. Kessler, Angew. Chem. Int. Ed. 2002, 41, 3767-3773;
30. d) J. Ojima, S. Chakravarty, Q. Dong, Bioorg. Med. Chem. 1995, 3, 337-360;
31. e) E. Georges-Labousse, N. Messaddeq, G. Yehia, L. Cadalbert, A. Dierich, M. LeMeur, Nature Gen. 1996, 13, 370-373;
32. f) D. R. Phillips, P. B. Conley, U. Sinha, P. Andre, J. Thromb. Haemost. 2005, 8, 1577-1589;
33. g) G. C. Tucker, Curr. Oncol Rep. 2006, 2, 96-103.
34. J.-P. Xiong, T. Stehle, R. Zhang, A. Joachimiak, M. Frach, S. L. Goodman, M. A. Arnaout, Science 2002, 296, 151-155, PDB file deposited with code 1L5G.
35. F. Benfatti, G. Cardillo, L. Gentilucci, E. Mosconi, A. Tolomelli, Org. Lett. 2008, 10, 2425-2428.
36. G. Cardillo, S. Fabbroni, L. Gentilucci, M. Gianotti, A. Tolomelli, Synt, Commun, 2003, 33, 1587-1594.
37. F. Benfatti, G. Cardillo, L. Gentilucci, E. Mosconi, A. Tolomelli, Tetrahedron: Asymmetry 2007, 18, 2227-2233.
38. B. Li, M. Berliner, R. Buzon, C. K.-F. Chiu, S. T. Colgan, T. Kaneko, N. Keene, W Kissel, T. Le, K. R. Leeman, B. Marquez, R. Morris, L. Newell, S. Wunderwald, M. Witt, J. Weaver, Z. Zhang, Z. Zhang, J. Org. Chem. 2006, 71, 9045-9050.