Microwave-assisted cyclization of peptides on SynPhase™ lanterns

Synlett

Volumn , Issue 9, 2006, Pages 1311-1314

  Monroc, Sylvie ^a   Feliu, Lidia ^a   Planas, Marta ^a   Bardají, Eduard ^a  

^a UNIVERSITY OF GIRONA   (Spain)

Author keywords

Cyclic peptides; Cyclization; Microwave; SynPhase lanterns

Indexed keywords

CYCLOPEPTIDE;

AMINO ACID SEQUENCE; ARTICLE; CYCLIZATION; LABORATORY APPARATUS, EQUIPMENT AND SUPPLIES; METHODOLOGY; MICROWAVE RADIATION;

EID: 33745357631     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-939717     Document Type: Article

References (27)

1. (a) Davidson, B. S. Chem. Rev. 1993, 93, 1771.
2. (b) Fusetani, N.; Matsunaga, S. Chem. Rev. 1993, 93, 1793.
3. (c) De Lucca, A. J.; Walsh, T. J. Rev. Iberoam. Micol. 2000, 17, 116.
4. (d) Aneiros, A.; Garateix, A. J. Chromatogr. B 2004, 803, 41.
5. (a) Toniolo, C. Int. J. Pept. Protein Res. 1990, 35, 287.
6. (b) Fairlie, D. P.; Abbenante, G.; March, D. R. Curr. Med. Chem. 1995, 2, 654.
7. (c) Cowell, S. M.; Lee, Y. S.; Cain, J. P.; Hruby, V. J. Curr. Med. Chem. 2004, 11, 2785.
8. (a) Wipf, P. Chem. Rev. 1995, 95, 2115.
9. (b) Humphrey, J. M.; Chamberlin, A. R. Chem. Rev. 1997, 97, 2243.
10. (c) Lambert, J. N.; Mitchell, J. P.; Roberts, K. D. J. Chem. Soc., Perkin Trans. 1 2001, 471.
11. (d) Horton, D. A.; Bourne, G. T.; Smythe, M. L. J. Comput. Aided Mol. Des. 2002, 16, 415.
12. (e) Davies, J. S. J. Peptide Sci. 2003, 9, 471.
13. (f) Alcaro, M. C.; Sabatino, G.; Uziel, J.; Chelli, M.; Ginanneschi, M.; Rovero, P.; Papini, A. M. J. Pept. Sci. 2004, 10, 218.
14. (a) Planas, M.; Bardají, E.; Barany, G. Tetrahedron Lett. 2000, 41, 4097.
15. (b) Cros, E.; Planas, M.; Barany, G.; Bardají, E. Eur. J. Org. Chem. 2004, 3633.
16. (a) Geysen, H. M.; Meloen, R. H.; Barteling, S. J. Proc. Natl. Acad. Sci. U.S.A. 1984, 81, 3998.
17. (b) Subra, G.; Soulère, L.; Hoffmann, P.; Enjalbal, C.; Aubagnac, J.-L.; Martinez, J. QSAR Comb. Sci. 2003, 22, 646.
18. (c) Feliu, L.; Subra, G.; Martinez, J.; Amblard, M. J. Comb. Chem. 2003, 5, 356.
19. (a) Loupy, A. Microwaves in Organic Synthesis; Wiley-VCH: Weinheim, 2002.
20. (b) Santagada, V.; Perissutti, E.; Caliendo, G. Curr. Med. Chem. 2002, 9, 1251.
21. (c) Kappe, C. O. Angew. Chem. Int. Ed. 2004, 43, 6250.
22. Grieco, P.; Campiglia, P.; Gomez-Monterrey, I.; Lama, T.; Novellino, E. Synlett 2003, 2216.
23. Kates, S. A.; Solé, N. A.; Johnson, C. R.; Hudson, D.; Barany, G.; Albericio, F. Tetrahedron Lett. 1993, 34, 1549.
24. SynPhase™ lanterns were purchased from Mimotopes, Pty Ltd, Clayton, Australia.
25. 2 (5 × 5 min).
26. Basso, A.; Ernst, B. Tetrahedron Lett. 2001, 42, 6687.
27. 2O, centrifuged and decanted. The final cyclopeptide was analyzed by HPLC and characterized by FAB-MS or ESI-MS.