Syntheses and Activities of New C10 β-Turn Peptidomimetics

Journal of Organic Chemistry

Volumn 69, Issue 3, 2004, Pages 701-713

  Lee, Hong Boon ^a   Zaccaro, Maria Clara ^b   Pattarawarapan, Mookda ^a   Roy, Sudipta ^a   Saragovi, H Uri ^b   Burgess, Kevin ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

^b MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CELLS; SOLUBILITY; SYNTHESIS (CHEMICAL);

SOLID-PHASE MODIFICATIONS;

PROTEINS;

NERVE GROWTH FACTOR; NEUROTROPHIN; NEUROTROPHIN 3; PEPTIDE DERIVATIVE;

ARTICLE; CATALYSIS; CONFORMATIONAL TRANSITION; PEPTIDE SYNTHESIS; PROTEIN PROTEIN INTERACTION; REACTION ANALYSIS; SOLID; SOLUBILITY;

AMINO ACIDS; ANIMALS; BINDING, COMPETITIVE; BIOMIMETIC MATERIALS; CELL SURVIVAL; MICE; MODELS, MOLECULAR; NERVE GROWTH FACTOR; NEUROTROPHIN 3; NIH 3T3 CELLS; PEPTIDES, CYCLIC; PROTEIN STRUCTURE, SECONDARY; RECEPTOR, TRKA; RECEPTOR, TRKC;

EID: 0842307443     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034167x     Document Type: Article

References (42)

1. Searle, M. S.; Williams, D. H. J. Am. Chem. Soc. 1992, 114, 10690.
2. Gerhard, U.; Searle, M. S.; Williams, D. H. Bioorg. Med. Chem. Lett. 1993, 3, 803.
3. Mammen, M.; Choi, S.-K.; Whitesides, G. M. Angew. Chem., Int. Ed. 1998, 37, 2754.
4. Rose, G. D.; Gierasch, L. M.; Smith, J. A. Turns in Peptides and Proteins; Academic Press: New York, 1985; Vol. 37.
5. Feng, Y.; Wang, Z.; Jin, S.; Burgess, K. J. Am. Chem. Soc. 1998, 120, 10768.
6. Feng, Y.; Burgess, K. Chem.-Eur. J. 1999, 5, 3261.
7. Feng, Y.; Burgess, K. Biotechnol. Bioeng. Comb. Chem. 2000, 71, 3.
8. Park, C.; Burgess, K. J. Comb. Chem. 2001, 3, 257.
9. LeSauteur, L.; Wei, L.; Gibbs, B.; Saragovi, H. U. J. Biol. Chem. 1995, 270, 6564.
10. Beglova, N.; LeSauteur, L.; Ekiel, I.; Saragovi, H. U.; Gehring, K. J. Biol. Chem. 1998, 273, 23652.
11. Maliartchouk, S.; Feng, Y.; Ivanisevic, L.; Debeir, T.; Cuello, A. C.; Burgess, K.; Saragovi, H. U. Mol. Pharm. 2000, 57, 385.
12. Berteina, S.; Mesmaeker, A. D. Synlett 1998, 1227.
13. Mutter, M.; Hersperger, R. Synthesis 1989, 198.
14. Hudlicky, M.; Reductions in Organic Chemistry; Wiley: New York, 1984.
15. Rink, H. Tetrahedron Lett. 1987, 28, 3787.
16. Neustadt, B. R.; Smith, E. M.; Nechuta, T.; Zhang, Y. Tetrahedron Lett. 1998, 39, 5317.
17. NovaBiochem Catalog & Peptide Synthesis Handbook; NovaBiochem: Darmstadt, 1999.
18. Mayer, J. P.; Zhang, J.; Bjergarde, K.; Lenz, D. M.; Gaudino, J. J. Tetrahedron Lett. 1996, 37, 8081.
19. Arumugam, V.; Routledge, A.; Abell, C.; Balasubramanian, S. Tetrahedron Lett. 1997, 38, 6473.
20. Lee, J.; Gauthier, D.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 201.
21. Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Anal. Biochem. 1970, 34, 595.
22. Rich, D. H.; Gurwara, S. K. Tetrahedron Lett. 1975, 16, 301.
23. Gelb, M. H.; Abeles, R. H. J. Med. Chem. 1986, 29, 585.
24. Coste, J.; Frerot, E.; Jouin, P. Tetrahedron Lett. 1991, 32, 1967.
25. Guarna, A.; Guidi, A.; Machetti, F.; Menchi, G.; Occhiato, E. G.; Scarpi, D.; Sisi, S.; Trabocchi, A. J. Org. Chem. 1999, 64, 7347.
26. Humphrey, J. M.; Chamberlin, A. R. Chem. Rev. 1997, 97, 2243.
27. Bunin, B. A.; Ellman, J. A. J. Am. Chem. Soc. 1992, 114, 10997.
28. Wang, H.; Ganesan, A. J. Comb. Chem. 2000, 2, 186.
29. Feng, Y.; Wang, Z.; Jin, S.; Burgess, K. Chem.-Eur. J. 1999, 5, 3273.
30. Pattarawarapan, M.; Zaccaro, M. C.; Saragovi, U.; Burgess, K. J. Med. Chem 2002, 45, 4387.
31. Urfer, R.; Tsoulfas, P.; O'Connell, L.; Shelton, D. L.; Parada, L. F.; Presta, L. G. EMBO 1995, 14, 2795.
32. Perez, P.; Coll, P. M.; Hempstead, B. L.; Martin-Zanca, D.; Chao, M. V. Mol. Cell. Neurosci. 1995, 6, 97.
33. Urfer, R.; Tsoulfas, P.; O'Connell, L.; Hongo, J.-A.; Zhao, W.; Presta, L. G. J. Biol. Chem. 1998, 273, 5829.
34. Yong, Y. F.; Kowalski, J. A.; Lipton, M. A. J. Org. Chem. 1997, 62, 1540.
35. Navia, M. A.; Chaturvedi, P. R. Drug Discovery Today 1996, 1, 179.
36. Chan, O. H.; Stewart, B. H. Drug Discovery Today 1996, 1, 461.
37. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Adv. Drug Delivery Rev. 1997, 23, 3.
38. Walters, W. P.; Ajay, Murcko, M. A. Curr. Opin. Chem. Biol. 1999, 3, 384.
39. Nicolas, E.; Clemente, J.; Ferrer, T.; Albericio, F.; Giralt, E. Tetrahedron 1997, 53, 3179.
40. LeSauteur, L.; Malartchouk, S.; LeJeune, H.; Quirion, R.; Saragovi, H. U. J. Neurosci. 1996, 16, 1308.
41. Saragovi, H. U.; Zheng, W.; Maliartchouk, S.; DiGugliemo, G. M.; Mawal, Y. R.; Kamen, A.; Woo, S. B.; Cuello, A. C.; Debeir, T.; Neet, K. E. J. Biol. Chem. 1998, 273, 34933.
42. Maliartchouk, S.; Saragovi, H. U. J. Neurosci. 1997, 17, 6031.