Solid-phase guanidinylation as a diversification strategy of poly-L-proline type II peptide mimic scaffolds

Organic Letters

Volumn 3, Issue 4, 2001, Pages 561-564

  Mamai, Ahmed ^a   Madalengoitia, Jose S ^a  

^a UNIVERSITY OF VERMONT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GUANIDINE; PEPTIDE; POLYPROLINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; MOLECULAR MIMICRY;

GUANIDINE; MOLECULAR MIMICRY; MOLECULAR STRUCTURE; PEPTIDES;

EID: 0035932043     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0069711     Document Type: Article

References (27)

1. For a review see: Siligardi, G.; Drake, A. F. Pept. Sci. 1995, 37, 281.
2. (a) Raj, P. A.; Marcus, E.; Edgerton, M. Biochemistry 1996, 35, 4314.
3. (b) Lee, C.-H.; Saksela, K.; Mirza, U. A.; Chait, B. T.; Kuriyan, J. Cell 1996, 85, 931.
4. (c) Peng, S.; Kasahara, C.; Rickles, R. J.; Schreiber, S. L. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 12408
5. (d) Jardetzky, T. S.; Brown, J. H.; Gorga, J. C.; Stern, L. J.; Urban, R. G.; Strominger, J. L.; Wiley, D. C. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 734.
6. (e) Zeile, W. L.; Punch, D. L.; Southwick, F. S. J. Cell Biol. 1996, 133, 49.
7. (a) Zhang, R.; Brownewell, F.; Madalengoitia, J. S. J. Am. Chem. Soc. 1998, 120, 3894.
8. (b) Zhang, R.; Madalengoitia, J. S. J. Org. Chem. 1999, 64, 330.
9. Zhang, R.; Mamai, A.; Madalengoitia, J. S. J. Org. Chem. 1999, 64, 547.
10. (a) Feichtinger, K.; Zapf, C.; Sings, H. L.; Goodman, M. J. Org. Chem. 1998, 63, 3804.
11. (b) Feichtinger, K.; Sings, H. L.; Baker, T. J.; Matthews, K.; Goodman, M. J. Org. Chem. 1998, 63, 8432.
12. (c) Linton, B. R.; Carr, A. J.; Orner, B. P.; Hamilton, A. D. J. Org. Chem. 2000, 65, 1566.
13. (d) Kim, K. S.; Qian, L. Tetrahedron Lett. 1993, 34, 7677.
14. (e) Bernatowicz, M. S.; Wu, Y.; Matsueda, G. R. Tetrahedron Lett. 1993, 34, 3389,
15. (f) Poss, M. A. Iwanowicz, E.; Reid, J. A.; Lin, J.; Gu, Z. Tetrahedron Lett. 1992, 33, 5933.
16. (g) Yong, Y. F.; Kowalski, J. A.; Lipton, M. A. J. Org. Chem. 1997, 62, 1540.
17. (h) Robinson, S.; Roskamp, E. J. Tetrahedron 1997, 53, 6697.
18. Dodd, D. S.; Wallace, O. B. Tetrahedron Lett. 1998, 39, 5701.
19. (j) Wilson, L. J.; Klopfenstein, S. R.; Li, M. Tetrahedron Lett. 1999, 40, 3999.
20. (k) Dodd, D. S.; Kozikowski, A. P. Tetrahedron Lett. 1994, 35, 977.
21. Zhao, M.; Li, J.; Mano, E.; Song, Z.; Tsachen, D. M.; Grabowski, E. J. J.; Reider, P. J. J. Org. Chem. 1999, 64, 2564.
22. Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009.
23. The yield of peptide 12 is without trituration because it was found to be ether-soluble.
24. The synthesis of 20 was repeated, but 20 was still obtained in lower purity than the other compounds.
25. (a) Yajima, H.; Fujii, N.; Funakoshi, N.; Watanabe, T.; Murayama, E.; Otaka, A. Tetrahedron 1988, 44, 805.
26. (b) Hughes, J. L.; Leopold, E. J. Tetrahedron Lett. 1993, 34, 7713.
27. 2O).