Modular synthesis of cyclic peptidomimetics inspired by γ-turns

Organic Letters

Volumn 7, Issue 6, 2005, Pages 1059-1062

  Ramanathan, Senthil Kumar ^a   Keeler, John ^a   Lee, Huey Lih ^a   Srinavasa Reddy, D ^a   Lushington, Gerald ^a   Aubè, Jeffrey ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; AZIDE; DIAZEPINE DERIVATIVE; ETHER DERIVATIVE; HETEROCYCLIC COMPOUND; PIPERIDONE DERIVATIVE;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; HYDROLYSIS; REACTION ANALYSIS; SYNTHESIS;

AMINO ACIDS; AZEPINES; AZIDES; INDICATORS AND REAGENTS; MOLECULAR MIMICRY; MOLECULAR STRUCTURE; PEPTIDES, CYCLIC; PROTEIN CONFORMATION; STEREOISOMERISM;

EID: 18244376860     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047323a     Document Type: Article

References (43)

1. (a) Goodman, M.; Chorev, M. Acc. Chem. Res. 1979, 12, 1-7.
2. (b) Huffman, W. F.; Callahan, J. F.; Eggleston, D. S.; Newlander, K. A.; Takata, D. T.; Codd, E. E.; Walker, R. F.; Schiller, P. W.; Lemieux, C.; Wire, W. S.; Burks, T. F. In Peptides, Chemistry and Biology, Proceedings of the 10th Annual American Peptide Symposium; Marshall, G. R., Ed.; ESCOM: Leiden, 1988; pp 105-108.
3. (c) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244-1267.
4. (d) Marshall, G. R. Tetrahedron 1993, 49, 3547-3558.
5. (e) Olson, G. L.; Bolin, D. R.; Bonner, M. P.; Bös, M.; Cook, C. M.; Fry, D. C.; Graves, B. J.; Hatada, M.; Hill, D. E.; Kahn, M.; Madison, V. S.; Rusiecki, V. K.; Sarabu, R.; Sepinwall, J.; Vincent, G. P.; Voss, M. E. J. Med. Chem. 1993, 36, 3039-3049.
6. (f) Aubé, J. In Advances in Amino Acid Mimetics und Peptidomimetics; Abell, A., Ed.; JAI Press: Greenwich, CT. 1997; Vol. 1. pp 193-232.
7. (g) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854.
8. (h) MacDonald, M.; Aubé, J. Curr. Org. Chem 2001, 5, 417-438.
9. For leading reviews on β-turns and their mimics, see: Rose, G. D.; Gierasch, L. M.; Smith, J. A. In Advances in Protein Chemistry; Anfinsen, C. B., Edsall, J. T., Richards, F. M., Eds.; Academic: Orlando, 1985; Vol. 37, pp 1-109. See also ref 1 above.
10. (a) Hagler, A. T.; Osguthorpe, D. J.; Dauber-Osguthorpe, P.; Hempel, J. C. Science 1985, 227, 1309-1315.
11. (b) Kessler, H.; Holzemann, G.; Zechel, C. Int. J. Pept. Protein Res. 1985, 25, 267-269.
12. (c) Mammi, N. J.; Hassan, M.; Goodman, M. J. Am. Chem. Soc. 1985, 107, 4008-4013.
13. (d) Kemp, D. S.; Carter, J. S. Tetrahedron Lett. 1987, 28, 4645-4648.
14. (e) Kemp, D. S.; Carter, J. S. J. Org. Chem. 1989, 54, 109-115.
15. (f) Callahan, J. F.; Bean, J. W.; Burgess, J. L.; Eggleston, D. S.; Hwang, S. M.; Kopple, K. D.; Koster, P. F.; Nichols, A.; Peishoff, C. E.; Samanen, J. M.; Vasko, J. A.; Wong, A.; Huffman, W. F. J. Med. Chem. 1992, 35, 3970-3972.
16. (g) Peishoff, C. E.; Ali, F. E.; Bean, J. W.; Cairo, R.; D'Ambrosio, C. A.; Eggleston, D. S.; Kline, T. P.; Koster, P. F.; Hwang, S. M. J. Med. Chem. 1992, 35, 3962-3969.
17. (h) d'Ursi, A.; Pegna, M.; Amodeo, P.; Molinari, H.; Verdini, A.; Zetta, L.; Temussi, P. A. Biochemistry 1992, 31, 9581-9586.
18. (i) Palmer, D. E.; Pattaroni, C.; Nunami, K.; Chadha, R. K.; Goodman, M.; Wakamiya, T.; Fukase, K.; Horimoto, S.; Kitazawa, M.; Fujita, H.; Kubo, A.; Shiba, T. J. Am. Chem. Soc. 1992, 114, 5634-5642.
19. (j) Sato, M.; Lee, J. Y. H.; Nakanishi, H.; Johnson, M. E.; Chrisciel, R. A.; Kahn, M. Biochem. Biophys. Res. Commun. 1992, 187, 999-1006.
20. (k) Callahan, J. F.; Newlander, K. A.; Burgess, J. L.; Eggleston, D. S.; Nichols, A.; Wong, A.; Huffman, W. F. Tetrahedron 1993, 49, 3479-3488.
21. (l) Drewes, J. A.; Rowlen, K. L. Biophys. J. 1993, 65, 985-991.
22. (m) Lisowski, M.; Pietrzynski, G.; Rzeszotarska, B. Int. J. Pept. Protein Res. 1993, 42, 466-474.
23. (n) Moroder, L.; D'Ursi, A.; Picone, D.; Amodeo, P.; Temussi, P. A. Biochem. Biophys. Res. Commun. 1993, 190, 741-746.
24. (o) Newlander, K. A.; Callahan, J. F.; Moore, M. L.; Tomaszek, T. A., Jr.; Huffman, W. F. J. Med. Chem. 1993, 36, 2321-2331.
25. (p) Balaji, V. N.; Ramnarayan, K.; Chan, M. F.; Rao, S. N. Pharm. Res. 1994, 7, 60-71.
26. (q) Hoog, S. S.; Zhao, B.; Winborne, E.; Fisher, S.; Green, D. W.; DesJarlais, R. L.; Newlander, K. A.; Callahan, J. F.; Moore, M. L.; Huffman, W. F.; Abdel-Meguid, S. S. J. Med. Chem. 1995, 38, 3246-3252.
27. (r) Curran, T. P.; Chandler, N. M.; Kennedy, R. J.; Keaney, M. T. Tetrahedron Lett. 1996, 37, 1933-1936.
28. (s) Schmidt, B.; Lindman, S.; Tong, W.; Lindeberg, G.; Gogoll, A.; Lai, Z.; Thörnwall, M.; Synnergren, B.; Nilsson, A.; Welch, C. J.; Sohtell, M.; Westerlund, C.; Nyberg, F.; Karlen, A.; Hallberg, A. J. Med. Chem. 1997, 40, 903-919.
29. (t) Kocis, P.; Campbell, J. B.; Sparks, R. B.; Wildonger, R. High-Throughput Synth. 2001, 65-83.
30. (u) Wilson, S. R.; Reinhard, K. High-Throughput Synth. 2001, 55-64.
31. This is related to the retro-inverso concept of peptidomimetic design: (a) Ref 1a. (b) Chorey, M.; Goodman, M. Acc. Chem. Res. 1993, 26, 266-273.
32. This is related to the retro-inverso concept of peptidomimetic design: (a) Ref 1a. (b) Chorey, M.; Goodman, M. Acc. Chem. Res. 1993, 26, 266-273.
33. (a) Gracias, V.; Milligan, G. L.; Aubé, J. J. Am. Chem. Soc. 1995, 117, 8047-8048.
34. (b) Gracias, V.; Milligan, G. L.; Aubé, J. J. Org. Chem. 1996, 61, 10-11.
35. (c) Gracias, V.; Frank, K. E.; Milligan, G. L.; Aubé, J. Tetrahedron 1997, 53, 16241-16252.
36. (d) Sahasrabudhe, K.; Gracias, V.; Furness, K.; Smith, B. T.; Katz, C. E.; Reddy, D. S.; Aube, J. J. Am. Chem. Soc. 2003, 125, 7914-7922.
37. (e) Smith, B. T.; Gracias, V.; Aubé, J. J. Org. Chem. 2000, 65, 3771-3774.
38. (a) Zaloom, J.; Roberts, D. C. J. Org. Chem. 1981, 46, 5173-5176.
39. (b) Vasella, A.; Witzig, C.; Chiara, J. L.; Lomas, M. M. Helv. Chim. Acta 1991, 74, 2073-2077
40. (c) Hedenstrom, M.; Holm, L.; Yuan, Z. Q.; Emtenas, H.; Kihlberg, J. Bioorg. Med. Chem. Lett. 2002, 12, 841-844.
41. (d) Hedenstroem, M.; Yuan, Z.; Brickmann, K.; Carlsson, J.; Ekholm, K.; Johansson, B.; Kreutz, E.; Nilsson, A.; Sethson, I.; Kihlberg, J. J. Med. Chem. 2002, 45, 2501-2511.
42. Wendt, J. A.; Aubé, J. Tetrahedron Lett. 1996, 37, 1531-1534.
43. Conti, P.; Demont, D.; Cals, J.; Ottenheijm, H. C. J.; Leysen, D. Tetrahedron Lett. 1997, 38, 2915-2918.