A backbone linker for BOC-based peptide synthesis and on-resin cyclization: Synthesis of stylostatin 1

Journal of Organic Chemistry

Volumn 64, Issue 9, 1999, Pages 3095-3101

  Bourne, Gregory T ^a   Meutermans, Wim D F ^a   Alewood, Paul F ^a   McGeary, Ross P ^a   Scanlon, Martin ^a   Watson, Andrew A ^a   Smythe, Mark L ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPEPTIDE; HEPTAPEPTIDE; RESIN; STYLOSTATIN 1; UNCLASSIFIED DRUG;

ACYLATION; AMINATION; ARTICLE; CARBOXY TERMINAL SEQUENCE; CYCLIZATION; PEPTIDE SYNTHESIS;

EID: 0033617430     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9818780     Document Type: Article

References (37)

1. Jung, G.; Beck-Sickinger, A. G. Angew. Chem., Int. Ed. Engl. 1992, 31, 367-386.
2. Moos, W. H.; Green, G. D. Annu. Rep. Med. Chem. 1993, 28, 315-325.
3. Houghten, R. J. P. C.; Blonella, S. E.; Appel, J. R.; Dooley, C. T.; Cuervo, J. H. Nature 1991, 554, 84-86.
4. Chen, C.; Randall, L. A. A.; Miller, R. B.; Jones, A. D.; Kurth, M. J. J. Am. Chem. Soc. 1994, 116, 2661-2662.
5. Pavia, M. R.; Sayer, T. K.; Moos, W. J. J. Biorg. Med. Chem. Lett. 1993, 3, 387-396.
6. Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Foder, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233-1251.
7. Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Foder, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385-1401.
8. Spatola, A. F.; Crozet Y.; Dewit, D.; Yanagisawa, M. J. Med. Chem. 1996, 39, 3842-2846.
9. Giebel, L. B.; Cass, R. T.; Milligan, D. L.; Young, D. C.; Arze, R.; Johnson, C. R. Biochemistry 1995, 34, 15430-15435.
10. Bauer, W.; Briner, U.; Doepfner, W.; Haller, R.; Huguenin, R.; Marbach, P.; Petchr, T. J.; Pless, J. Life Sci. 1982, 31, 1133-1140.
11. Emmel, E. A.; Verweij, C. L.; Durand, D. B.; Higgins, K. M.; Lacy, E.; Crabtree, G. R. Science 1989, 246, 1617-1620.
12. Norshino, N.; Xu, M.; Mihara, H.; Fujimoto, T. Tetrahedron Lett. 1992, 33, 1479-1482.
13. Norshino, N.; Xu, M.; Mihara, H.; Fujimoto, T.; Ohba, M.; Ueno, Y.; Kumagai, K. J. Chem. Soc., Chem. Commun. 1992, 180-181.
14. Öspray, G.; Profit, A.; Taylor, J. W. Tetrahedron Lett. 1990, 31, 6121-6124.
15. Kapurniotu, A.; Taylor, J. W. Tetrahedron Lett. 1993, 34, 7031-7034.
16. Kates, S. A.; Solé, N. A.; Johnson, C. R.; Hudson, D.; Barany, G.; Albericio, F. Tetrahedron Lett. 1993, 34, 1549-1552.
17. Rovero, P.; Quartara, L.; Fabbri, G. Tetrahedron Lett. 1991, 32, 2639-2642.
18. Jensen, K. L.; Songster, M. F.; Vágner, J.; Alsina, J.; Albericio, F.; Barany, G. In Peptides: Chemistry, Structure and Biology (Proceedings of the 14th American Peptide Symposium); Kaumaya, P. T. P., Hodges, R. S., Eds.; Mayflower Scientific Ltd: U.K., 1996; Vol. 14, 30-32.
19. Jensen, K. J.; Alsini, J.; Songster, M. F.; Vágner, J.; Albericio, F.; Barany, G. J. Am. Chem. Soc. 1998, 120, 5441-5452.
20. Fresno, M.; Alsini, J.; Barany, G.; Albercio, F. Tetrahedron Lett. 1998, 39, 2639-2642.
21. Schnölzer, M.; Alewood, P.; Jones, A.; Alewood, D.; Kent, S. B. H. Int. J. Pept. Protein Res. 1992, 40, 180-193.
22. Ehrlich, A.; Klose, J.; Heyne, H.-U.; Beyermann, M.; Carpino, L. A.; Bienert, M. In Peptides: Chemistry, Structure and Biology (Proceedings of the 14th American Peptide Symposium); Kaumaya, P. T. P., Hodges, R. S., Eds.; Mayflower Scientific Ltd: U.K., 1996; Vol. 14, 75-76.
23. Pettit, G. R.; Srirangem, J. K.; Herald, D. L.; Erickson, K. L.; Doubek, D. L.; Schmidt, J. M.; Tackett, L. P.; Bakus, G. L. J. Org. Chem. 1992, 57, 7217-7220.
24. Spatola, A. F.; Romanovskis, P. Cyclic Peptide Libraries: Recent Developments. In Peptides and Non-Peptide Libraries- A Handbook for the Search of Lead Structures; Jung, G., Ed.; VCH Publishers: Weinheim, 1996; Chapter 11, 327-347.
25. Pettit, G. R.; Clewlow, P. J.; Dufresne, C.; Doubek, D. L.; Cerny, R. L.; Rützler, K. Can. J. Chem. 1990, 68, 708-711.
26. Konat, R. K.; Matha B.; Winkler J.; Kessler H. Liebigs Ann. Chem. 1995, 765-774.
27. Pettit, G. R.; Herald, D. L.; Boyd, M. R.; Leet, J. E.; Dufresne, C.; Doubek, D. L.; Schmidt, J. M.; Cerny, R. L.; Hooper, J. N. A.; Rützler, K. J. Med. Chem. 1991, 34, 3339-3340.
28. Pettit, G. R.; Srirangem, J. K.; Herald, D. L.; Jun-ping, X.; Boyd, M. R.; Cichacz, Z.; Kamano, Y.; Schmidt, J. M.; Erickson, K. L. J. Org. Chem. 1995, 60, 8257-8261.
29. Huang, Z.; Probstyl, A.; Spencer, J. R.; Yamazaki, T.; Goodman, M. Int. J. Pept. Protein Res. 1993, 42, 352-365.
30. Look, G.; Holmes, C. P.; Chin, J. P.; Gallop, M. J. Org. Chem. 1994, 59, 7588-7590.
31. Sasaki, Y.; Coy, D. H. Peptides 1987, 8, 119-126.
32. Merrifield, R. B.; Vizioli, L. D.; Boman, H. G. Biochemistry 1982, 21, 5020-5031.
33. Kaduk, C.; Wehschuh, H.; Beyermann, M.; Forner, K.; Carpino, L. A.; Bienert, M. Lett. Pept. Sci. 1995, 2, 285-289.
34. 29 Backbone atoms of synthetic stylostatin 1 superimpose on the X-ray structure of the native material with an RMSD of 0.51 ± 0.01 Å.
35. Leznoff, C. C. Chem. Soc. Rev. 1974, 3, 65-87.
36. McMurray, J. S.; Lewis, C. A.; Obeyesekere, N. U. Pept. Res. 1994, 7, 195-206.
37. Scanlon, M. J.; Naranjo, D.; Thomas, L.; Alewood, P. F.; Lewis, R. J.; Craik, D. J. Structure 1997, 5, 1585-1597.