Arylation of phe and tyr side chains of unprotected peptides by a Suzuki-Miyaura reaction in water

Organic Letters

Volumn 10, Issue 15, 2008, Pages 3243-3245

  Vilaró, Maria ^a   Arsequell, Gemma ^a   Valencia, Gregorio ^a   Ballesteros, Alfredo ^a   Barluenga, José ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

BIS(PYRIDINE)IODONIUM(I) TETRAFLUOROBORATE; CATION; IODOPROTEIN; LEUCINE ENKEPHALIN; PEPTIDE; PHENYLALANINE; PYRIDINE DERIVATIVE; TYROSINE;

ARTICLE; CHEMISTRY; SYNTHESIS;

ENKEPHALIN, LEUCINE; IODOPROTEINS; ONIUM COMPOUNDS; PEPTIDES; PHENYLALANINE; PYRIDINES; TYROSINE;

EID: 49649117503     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801009z     Document Type: Article

References (39)

1. (a) Sewald, N.; Jakubke, H. D. Peptides: Chemistry and Biology; Wiley-VCH: Weinheim, Germany, 2002.
2. (b) Handbook of Biologically Active Peptides; Kastin, A., Ed.; Academic Press: New York, 2006.
3. (a) Burk, M. J.; Lee, J. R.; Martinez, J. P. J. Am. Chem. Soc. 1994, 116, 10847-10848.
4. (b) Berezowska, I.; Chung, N. N.; Lemieux, C.; Wilkes, B. C; Schiller, P. W. J. Med. Chem. 2007, 50, 1414-1417.
5. (c) Agnes, R. S.; Lee, Y. S.; Davis, P.; Ma, S. W.; Badghisi, H.; Porreca, F.; Lai, J.; Hruby, V. J. J. Med. Chem. 2006, 49, 2868-2875.
6. (a) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.,; Stang, P. J., Eds.; Wiley-VCH: New York, 1998.
7. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
8. (c) Miyaura, N. Cross-Coupling Reaction; Springer: Berlin, 2002.
9. (d) Negishi, E. In Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley Interscience: New York, 2002.
10. (e) Beletskaya, I. P.; Cheprakov, A. V. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E; Ed.; Wiley-Interscience: New York, 2002, Vol. 2, pp 2957-3006.
11. 40. For Sonogashira cross-coupling reactions in 4-iodo-Phe peptides see: Dibowski, H; Schmidtchen, F. P. Angew. Chem., Int. Ed. 1998, 37, 476-478.
12. Gong, Y; He, W. Org. Lett. 2002, 4, 3803-3805.
13. (a) Kotha, S.; Lahiri, K. Biopolymers 2003, 69, 517-528.
14. (b) Basse, N.; Piguel, S.; Papapostolou, D.; Ferrier-Berthelot, A.; Richy, N.; Pagano, M.; Sarthou, P.; Sobczak-Thépot, J.; Reboud-Ravaux, M.; Vidal, J. J. Med. Chem. 2007, 50, 2842-2850.
15. (c) Bois-Choussy, M.; Cristeua, P.; Zhu, J. Angew. Chem., Int. Ed. 2003, 42, 4238-4241.
16. (d) Lépine, R.; Zhu, J. Org. Lett. 2005, 14, 2981-2984.
17. (e) Espuña, G.; Arsequell, G.; Valencia, G.; Barluenga, J.; Alvarez-Gutiérrez, J. M.; Ballesteros, A.; González, J. M. Angew. Chem., Int. Ed. 2004, 43, 325-329.
18. Doan, N. D.; Bourgault, S.; Létourneau, M.; Fournier, A. J. Comb. Chem. 2008, 10, 44-51.
19. (a) Kodama, K.; Fukuzawa, S.; Nakayama, H.; Sakamoto, K.; Kigawa, T.; Yabuki, T.; Matsuda, N.; Shirouzu, M.; Takio, K.; Yokoyama, S.; Tachibana, K. Chembiochem. 2007, 8, 232-238.
20. (b) Hoffmanns, U.; Metzler-Nolte, N. Bioconjug. Chem. 2006, 17, 204-213.
21. Ojidaa, A.; Tsutsumia, H.; Kasagia, N.; Hamachi, I. Tetrahedron Lett. 2005, 19, 3301-3305.
22. (a) Bumagin, N. A.; More, P. G.; Beletskaya, I. P. J. Organomet. Chem. 1989, 371-397.
23. (b) Bumagin, N. A.; Bykov, V. V.; Beletskaya, I. P. Izvest. Akad. Nauk. SSSR, Ser. Khim. 1989, 2394.
24. (c) Bumagin, N. A.; Bykov, V. V. Tetrahedron 1997, 53, 14437-14450.
25. (d) Dupusi, C.; Adiey, K.; Michelet, V.; Savignac, M.; Genet, J. P. Tetrahedron Lett. 2001, 42, 6523-6526.
26. (a) Collier, A.; Wagner, G. Org. Biomol. Chem. 2006, 4, 4526-4532.
27. (b) Capek, P.; Pohl, R.; Hocek, M. Org. Biomol. Chem. 2006, 4, 2278-2284.
28. (c) Western, E. C.; Daft, J. R.; Johnson, E. M.; Gannett, P. M.; Shaughnessy, K. H. J. Org. Chem. 2003, 68, 6767-6774.
29. (a) Hughes, J.; Smith, T. W.; Kosterlitz, H. W.; Fothergill, L. A.; Morgan, B. A.; Morris, H. R. Nature 1975, 258, 577-579.
30. (b) Zadina, J. E.; Hackler, L.; Ge, L. J.; Kastin, A. J. Nature 1997, 386, 499-502.
31. This combination has been previously used in the coupling of several biaryls and nucleosides and nucleotides in mixtures of water and different organic solvents: Casalnuovo, A. L.; Calabrese, J. C. J. Am. Chem. Soc. 1990, 112, 4324-4330.
32. 4) have also been tested at either room temperature or 50°C, see the Supporting Information.
33. For experimental data, see the accompanying Supporting Information.
34. For recent representative work, see: Espuña, G.; Andreu, D.; Barluenga, J.; Pérez, X.; Planas, A; Arsequell, G.; Valencia, G. Biochemistry 2006, 45, 5957-5963.
35. (a) Barluenga, J.; González, J. M. In Current Trends in Organic Synthesis; Scolastico, C., ; Nicotra, F., Eds.; Academic/Plenum Publishers: New York, 1999; pp 145-151.
36. (b) Barluenga, J. Pure Appl. Chem. 1999, 71, 431-436.
37. (a) Arsequell, G.; Espuña, G.; Valencia, G.; Barluenga, J.; Pérez Carlón, R.; González, J. M. Tetrahedron Lett. 1998, 39, 7393-7396.
38. (b) Arsequell, G.; Espuña, G.; Valencia, G.; Barluenga, J.; Pérez Carlón, R.; González, J. M. Tetrahedron Lett. 1999, 40, 7279-7282.
39. (c) Espuña, G.; Arsequell, G.; Valencia, G.; Barluenga, J.; Pérez, R.; González, J. M. Chem. Commun. 2000, 1307-1308.