A new conformationally restricted mimetic of dipeptide EG - Synthesis of an analogue of FEG

European Journal of Organic Chemistry

Volumn , Issue 26, 2007, Pages 4402-4407

  Galeazzi, Roberta ^a   Martelli, Gianluca ^a   Marcucci, Eleonora ^a   Mobbili, Giovanna ^a   Natali, Desiré ^a   Orena, Mario ^a   Rinaldi, Samuele ^a  

^a UNIVERSITÀ POLITECNICA DELLE MARCHE   (Italy)

Author keywords

Active conformation; Conformation analysis; Conformational restriction; Mimetics; Molecular modeling; Peptides

Indexed keywords

EID: 34548808122     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700300     Document Type: Article

References (42)

1. a) S. Hanessian, G. McNaughton-Smith, H. G. Lombart, W. D. Lubell, Tetrahedron 1997, 53, 12789-12854;
2. b) S. Kotha, Acc. Chem. Res. 2003, 36, 342-351;
3. c) "Synthesis of Peptides and Peptidomimetics", in Houben-Weyl, Methods in Organic Chemistry (Eds.: M. Goodman, A. Felix, L. Moroder, C. Toniolo), Thieme, Stuttgart, New York, 2003, vol. E22c.
4. a) J. A. Brannigan, A. J. Wilkinson, Nat. Rev. Mol. Cell Biol. 2002, 3, 964-970;
5. b) C. H. Collins, Y. Yokobayashi, D. Umeno, F. H. Arnold, Curr. Opin. Biotechnol. 2003, 14, 371-378;
6. c) S. Lutz, W. M. Patrick, Curr. Opin. Biotechnol. 2004, 15, 291-297;
7. d) Y. Lu, Curr. Opin. Chem. Biol. 2005, 9, 118-126.
8. a) A. Loffet, J. Pept. Sci. 2002, 8, 1-7;
9. b) V. J. Hruby, Nat. Rev. Drug Discovery 2002, 1, 847-858;
10. c) M. G. Bursavich, D. H. Rich, J. Med. Chem. 2002, 45, 541-558.
11. For recent papers, see: a) R. Galeazzi, G. Martelli, G. Mobbili, M. Orena, S. Rinaldi, Tetrahedron: Asymmetry 2003, 14, 3353-3358;
12. b) R. Galeazzi, G. Martelli, G. Mobbili, M. Orena, S. Rinaldi, Tetrahedron: Asymmetry 2004, 15, 3249-3256;
13. c) R. Galeazzi, G. Martelli, D. Natali, M. Orena, S. Rinaldi, Tetrahedron: Asymmetry 2005, 16, 1779-1787.
14. R. Mathison, P. Lo, G. Moore, B. Scott, J. S. Davison, Peptides 1998, 19, 1037-1042.
15. E. Metwally, J. M. Pires, G. J. Moore, D. A. Befus, J. S. Davison, R. Mathison, Peptides 2002, 23, 193-199.
16. R. D. Mathison, J. S. Davison, E. Metwally, Peptides 2003, 21, 1221-1230.
17. E. Metwally, H. A. Ismail, J. S. Davison, R. Mathison, Biophys. J. 2003, 85, 1503-1511.
18. F. Turesin, A. Sadr, J. S. Davison, R. Mathison, BMC Physiol. 2002, 2, 13 (http://www.biomedcentral.com/1472-6793/2/13).
19. R. E. Dery, M. Ulanova, L. Puttagunta, G. R. Stenton, D. James, S. Merani, R. Mathison, J. Davison, A. D. Befus, Eur. J. Immunol. 2004, 34, 3315-3325.
20. R. D. Mathison, J. S. Davison, A. D. Befus, Proc. West. Pharmacol. Soc. 2001, 44, 157-158.
21. R. Mathison, P. Lo, D. Tan, B. Scott, J. S. Davison, Neurogastroenterol. Motil. 2001, 13, 599-603.
22. a) R. Mathison, R. Woodman, J. S. Davison, Can. J. Physiol. Pharmacol. 2001, 79, 785-792;
23. b) F. Bao, S. M. John, Y. Chen, R. D. Mathison, L. C. Weaver, Neuroscience 2006, 14, 1011-1022.
24. a) R. Mathison, A. D. Befus, J. S. Davison, R. C. Woodman, BMC Immunol. 2003, 4, 3 (http://www.biomedcentral.com/ 1471-2172/4/3);
25. b) R. Mathison, Curr. Immunol. Rev. 2006, 2, 247-259;
26. c) R. D. Mathison, J. S. Davison, J. Inflammation 2006, 3, 9 (http://www.journal-inflammation.com/content/3/1/ 9).
27. R. Galeazzi, G. Martelli, M. Orena, S. Rinaldi, P. Sabatino, Tetrahedron 2005, 61, 5465-5473.
28. a) J. Aubé, "Synthetic routes to lactam peptidomimetics" , in Advances in amino acid mimetics and peptidomimetics (Ed.: A. Abell), JAI Press, Inc., Greenwich, CT, 1997, vol. 1, pp. 193-232;
29. b) R. M. Freidinger, J. Med. Chem. 2003, 46, 5553-5566;
30. c) K. Dolbeare, G. F. Pontoriero, S. K. Gupta, R. K. Mishra, R. L. Johnson, J. Med. Chem. 2003, 46, 727-733;
31. d) J. Podlech, D. Seebach, Liebigs Ann. 1995, 1217-1228.
32. See, for example: a) A. Gaucher, L. Dutot, O. Barbeau, W. Hamchaoui, M. Wakselman, J. P. Mazaleyrat, Tetrahedron: Asymmetry 2005, 16, 857-864;
33. b) J. Spengler, J. Ruiz-Rodriguez, K. Burger, F. Albericio, Tetrahedron Lett. 2006, 47, 4557-4560.
34. See, for relevant examples: a) H. T. Le, I. B. Lemaire, A. K. Gilbert, F. Jolicoeur, S. Lemaire, J. Med. Chem. 2003, 46, 3094-3101;
35. b) H. R. Lijnen, B. Van Hoef, D. Collen, Eur. J. Biochem. 1987, 162, 351-356;
36. c) D. Wernicke, C. Thiel, C. M. Duja-Isac, K. V. Essin, M. Spindler, D. J. R. Nunez, R. Plehm, N. Wessel, A. Hammes, R.-J. Edwards, A. Lippoldt, U. Zacharias, H. Strömer, S. Neubauer, M. J. Davies, I. Morano, L. Thierfelder, Am. J. Physiol.: Regul., Integr. Comp. Physiol. 2004, 287, R685-R695.
37. a) S. J. Weiner, P. A. Kollman, D. T. Nguyen, D. A. Case, J. Comput. Chem. 1986, 7, 230-252;
38. b) F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, W. C. Still, J. Comput. Chem. 1990, 11, 440-467;
39. c) J. M. Goodman, W. C. Still, J. Comput. Chem. 1991, 12, 1110-1117.
40. W. C. Still, A. Tempczyk, R. C. Hawley, T. Hendrickson, J. Am. Chem. Soc. 1990, 112, 6127-6129.
41. J. V. Ryzin, Classification and clustering, Academic Press, New York, 1977.
42. J. Zupan, Algorithms for Chemists, Wiley-VCH, New York, 1989, chapter 7.