Solid-phase synthesis and structural analysis of bicyclic β-turn mimetics incorporating functionality at the i to i + 3 positions [11]

Journal of the American Chemical Society

Volumn 121, Issue 51, 1999, Pages 12204-12205

  Eguchi, Masakatsu ^a,b   Lee, Min S ^a,b   Nakanishi, Hiroshi ^a,b   Stasiak, Marcin ^a   Lovell, Scott ^b   Kahn, Michael ^a,b  

^a Molecumetics Ltd   (United States)

^b UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PEPTIDE;

CHEMICAL STRUCTURE; DRUG RESEARCH; LETTER; MOLECULAR DYNAMICS; PROTEIN PROTEIN INTERACTION; PROTEIN SECONDARY STRUCTURE; SYNTHESIS;

EID: 0033616089     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992203x     Document Type: Letter

References (38)

1. Rose, G. D.; Gierasch, L. M.; Smith, J. A. Adv. Protein. Chem. 1985, 37, 1-109.
2. (a) Hruby, V. J.; Al-Obeidi, F.; Kazmierski, W. Biochem. J. 1990, 268, 249-262.
3. (b) Wiley, R. A.; Rich, D. H. Med. Res. Rev. 1993, 13(3), 327-384.
4. (c) 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.
5. (d) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244-1267.
6. (e) Gante, J. ibid. 1994, 33, 1699-1720.
7. (f) Fairlie, D. P.; West, M. L.; Wong, A. K. Curr. Med. Chem. 1998, 5, 29-62.
8. (a) Kahn, M. Ed. Tetrahedron 1993, 49, Symposia 50, 3433-3677.
9. (b) Hanessian, S.; McNaughton-Smith, G.; Lombart, H. G.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854 and references therein.
10. (c) Gillespie, P.; Cicariello, J.; Olson, G. L. Biopolymers 1997, 43, 191-217 and references therein.
11. (d) Hanessian, S.; Huynh, H. K.; Reddy, G. V.; McNaughton-Smith, G.; Ernst, B.; Kolb, H. C.; Magnani, J.; Sweeley, C. Bioorg. Med. Chem. Lett. 1998, 8, 2803-2808.
12. (e) Fink, B. E.; Kym, P. R.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1998, 120, 4334-4344.
13. (f) Hirschmann, R.; Hynes, J.; Cichy-Knight, M. A.; van Rijn, R. D.; Sprengeler, P. A.; Spoors, P. G.; Shakespeare, W. C.; Pietranico-Cole, S.; Barbosa, J.; Liu, J.; Yao, W.; Rohrer, S.; Smith, A. B., III, J. Med. Chem. 1998, 41, 1382-1391 and references therein.
14. (g) Johannesson, P.; Lindeberg, G.; Tong, W.; Gogoll, A.; Karlén, A.; Hallberg, A. ibid. 1999, 42, 601-608.
15. (h) Khalil, E. M.; Ojala, W. H.; Pradhan, A.; Nair, V. D.; Gleason, W. B.; Mishra, R. K.; Johnson, R. L. ibid. 1999, 42, 628-637.
16. (a) Kahn, M. Synlett. 1993, 11, 821-826 and references therein.
17. (b) Virgilio, A. A.; Ellman, J. A. J. Am. Chem. Soc. 1994, 116, 11580-11581.
18. (c) Virgilio, A. A.; Schürer, S. C.; Ellman, J. A. Tetrahedron Lett. 1996, 37, 6961-6964.
19. (d) Virgilio, A. A.; Bray, A. A.; Zhang, W.; Trinh, L.; Snyder, M.; Morrissey, M. M.; Ellman, J. A. Tetrahedron 1997, 53, 6635-6644.
20. (e) Feng, Y.; Wang, Z.; Jin, S.; Burgess, K. J. Am. Chem. Soc. 1998, 120, 10768-10769.
21. (a) Souers, A. J.; Virgilio, A. A.; Schürer, S. S.; Ellman, J. A.; Kogan, T. P.; West, H. E.; Ankener, W.; Vanderslice, P. Bioorg. Med. Chem. Lett. 1998, 8, 2297-2302.
22. (b) Souers, A. J.; Virgilio, A. A.; Rosenquist, A.; Fenuik, W.; Ellman, J. A. J. Am. Chem. Soc. 1999, 121, 1817-1825.
23. (a) Baldwin, J. E.; Hulme, C.; Edwards, A. J.; Schofield, C. J. Tetrahedron Lett. 1993, 34, 1665-1668.
24. (b) Vojkovsky, T.; Weichsel, A.; Pátek, M. J. Org. Chem. 1998, 63, 3162-3163.
25. Raman, P.; Stokes, S. S.; Angell, Y. M.; Flentke, G. R.; Rich, D. H. J. Org. Chem. 1998, 63, 5734-5735.
26. Asymmetric synthesis of a-substituted β-amino acids: (a) Cole, D. C. Tetrahedron 1994, 50, 9517-9582 and references therein.
27. (b) Juaristi, E.; Quintana, D.; Balderas, M.; Gareía-Pérez, E. Tetrahedron Asymmetry 1996, 7, 2233-2246.
28. (c) Rottmann, A.; Bartoczek, M.; Liebscher, J. Synthesis 1997, 313-327.
29. (d) Arvanitis, E.; Ernst, H.; Ludwig, A. A.; Robinson, A. J.; Wyatt, P. B. J. Chem. Soc., Perkin Trans. 1 1998, 3, 521-528 and references therein.
30. (e) Guichard, G.; Abele, S.; Seebach, D. Helv. Chim. Acta 1998, 81(2), 187-206 and references therein.
31. Thieriet, N.; Alsina, J.; Giralt, E.; Guibé, F.; Albericio, F. Tetrahedron Lett. 1997, 38, 7275-7278.
32. The cyclization for 4f was carried out at 55 °C for 4 h.
33. Most of the derivatives of type 4 exist as a mixture of two rotamers about the urethane linkage.
34. w = 0.1010, GOF = 1.084.
35. MacroModel V 6.0: Mohanmadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
36. Wilmot, C. M.; Thornton, J. M. J. Mol. Biol. 1988, 203, 221-232.
37. 3OD, which suggests that, although the benzyl group is axial, both benzyl and phenylsulfonyl groups maintain some distance from each other in relatively hydrophobic solvent system.
38. α(i + 3) atoms of ideal β-turns.