Solid-Phase Synthesis of Cyclosporin Peptides

Journal of the American Chemical Society

Volumn 117, Issue 27, 1995, Pages 7279-7280

  Angell, Yvonne M ^a   Thomas, Timothy L ^a   Flentke, George R ^a   Rich, Daniel H ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0028796640     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00132a042     Document Type: Article

References (36)

1. Rüegger. A.; Kuhn, M.; Lichti, H.; Loosli, H.R.; Huguenin, R.; Quiquerez. C.; von Wartburg, A. Cyclosporin A. ein immunsuppressiv wirksamer Peptidmetabolit aus Trichoderma polysporum (Link ex Pers.) Rifai. Helv. Chim. Acta. 1976, 59, 1075.
2. Borel, J.F.; Feurer. C.; Gubler, H.U.; Stähelin, H. Agents Actions 1976, 6, 468.
3. Dreyfuss, M.; Härri, E.; Hofmann. H.; Kobel, H.; Pache, W.; Tscherter, H. Eur. J. Appl. Microbiol. 1976, 3, 125.
4. Wenger, R.M. Helv. Chim. Acta 1983. 66, 2672.
5. Wenger, R.M. Helv. Chim. Acta 1984, 67, 502.
6. Wenger, R.M. Angew. Chem., Int. Ed. Engl. 1985, 24, 77.
7. Rich, D.H.; Dhaon, M.K.: Dunlap, B.; Miller, S.P.F. J. Med. Chem. 1986, 29, 978–984.
8. Colucci. W.J.; Tung, R.D.; Petri, J.A.: Rich. D.H. J. Org. Chem. 1990, 55, 2895—2903.
9. Merrifield, R.B. J. Am. Chem. Soc. 1963, 85, 2149—2154.
10. Merrifield, R.B. Science 1986. 232, 341–347.
11. Coste, J.; Frérot, E.; Jouin, P.; Castro. B. Tetrahedron Lett. 1991, 32, 1967—1970.
12. Wenschuh, H.; Beyermann, M.; Krause, E.; Carpino. L.A.: Bienert, M. Tetrahedron Lett. 1993, 34, 3733—3736.
13. Spencer, J.R.; Antonenko, V.V.; Dalaet. N.G.J.; Goodman. M. Int. J. Pep. Protein Res. 1992, 40, 282.
14. Frérot, E.; Coste. J.; Pantaloni, A.; Dufour, M.-N.: Jouin. P. Tetrahedron 1991, 47, 259.
15. Angell, Y.M.; Garcfa-Echeverrfa, C.; Rich. D.H. Tetrahedron Lett. 1994. 35, 5981–5984.
16. Carpino, L.A. J. Am. Chem. Soc. 1993. 115, 4397–4398.
17. Carpino, L.A.; El-Faham, A.; Albericio. F. Tetrahedron Lett. 1994, 35, 2279–2282.
18. Carpino, L.A.; El-Faham, A.; Minor, C.A.; Albericio, F. J. Chem. Soc., Chem. Commun. 1994. 201.
19. Abdelmoty, I.; Albericio. F.: Carpino, L.A.; Foxman, B.M.; Kates. S.A. Lett. Pept. Sci. 1994. 1, 57.
20. Carpino, L.A.; Han, G.Y. J. Org. Chem. 1972, 37, 3404.
21. Zalipsky, S.; Albericio, F.; Barany, G. In Peptides: Proceedings of the Ninth American Peptide Symposium: Deber, C.M., Hruby, V.J. Kopple, K.D. Eds.; Pierce Chemical Co.: Rockford. IL. 1985; p 257.
22. Barany, G.; Albericio, F.; Solé, N.A.; Griffin, G.W.; Kates, S.A.; Hudson. D. In Peptides: 1992: Proceedings of the Twenty-second European Peptide Symposium; Schneider, C.H., Eberle, A.N., Eds.; Escom: Leiden, The Netherlands, 1993; p 267.
23. Zalipsky, S.; Chang, J.L.; Albericio, F.; Barany, G. Reactive Polymers, in press.
24. Barany, G.; Albericio. F. In Peptides 1990: Proceedings of the Twenty -first European Peptide Symposium; Giralt. E., Andreu, D., Eds.; Escom: Leiden. The Netherlands, 1991; p 139.
25. Chang, C.-D.; Waki, M.; Ahmad. M.; Meienhofer, J.; Lundell. E.O.; Haug, J.D. Int. J. Pept. Protein Res. 1980, 15, 59—66.
26. Meienhofer. J.; Waki, M.: Heimer, E.P.; Lambros, T.J.; Makofske. R.C.; Chang, C.-D. Int. J. Pept. Protein Res. 1979, 13, 35—42.
27. Traber. R.; Hofmann, H.; Kobel, H. J. Antibiot. 1989. 42, 591.
28. Traber. R.; Hofmann, H.: Loosli. H.-R.: Ponelle, M.; von Wartburg, A. Helv. Chim. Acta. 1987, 70, 13.
29. von Wartburg, A.; Traber, R. In Progress in Medicinal Chemistry; Ellis, G.P., West, G.B., Eds.: Elsevier Science Publishers: Amsterdam, 1988, Vol. 25, pp 1–33.
30. Bartz, S.: Hohenwalter, E.; Hu, M.-K.; Rich, D.H.; Malkowsky, M. Inhibition of HIV Replication by Non-immunosuppressive Analogs of Cyclosporin A. Proc. Natl. Acad. Sci. U.S.A., in press.
31. Rich, D.H.; Hu, M.-K.; Bartz, S.; Hohenwalter, E.; Malkowsky, M. Inhibition of HIV Replication by Non-immunosuppressive Analogs of Cyclosporin A. Abstracts of Papers. 207th National Meeting of the American Chemical Society: American Chemical Society: Washington. DC, 1994.
32. Rosenwirth, B.; Billich, A.; Datema, R.; Donatsch, P.; Hammer-schmid, F.; Harrison, R.; Hiestand, P.; Jaksche. H.; Mayer, P.; Peichl, P.; Quesniaux, V.; Schatz, F.; Schuurman, H.-J.; Traber, R.; Wenger, R.; Wolff. B.; Zenke, G.: Zurini, M. Antimicrob. Agents Chemother. 1994, 38, 1763—1772.
33. Luban, J.; Bossolt, K.L.; Franke, E.K.; Kalpana, G.V.; Goff, S.P. Cell 1993, 73, 1067–1078.
34. Thali, M.; Bukovsky, A.; Kondo, E.; Rosenwirth, B.; Walsh, C.T.; Sodroski, J.; Gottlinger, H.G. Nature (London) 1994, 372, 363—365.
35. Mikol, V.; Kallen, J.; Pflugl, G.; Walkinshaw, M.D. J. Mol. Biol. 1993, 234, 1119–1130.
36. Ke, H.M.; Mayrose, D.; Belshaw, P.J.; Alberg, D.G.; Schreiber, S.L.; Chang, Z.Y.; Etzkorn, F.A.; Ho, S.; Walsh, C.T. Structure 1994, 2, 33–44.