Cysteine-S-trityl a key derivative to prepare N-methyl cysteines

Journal of Combinatorial Chemistry

Volumn 10, Issue 1, 2008, Pages 69-78

  Marcucci, Eleonora ^a   Bayó Puxan, Núria ^a   Tulla Puche, Judit ^a   Spengler, Jan ^a   Albericio, Fernando ^a,b  

^a INSTITUTE FOR RESEARCH IN BIOMEDICINE   (Spain)

^b UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

3 TRITYLTHIOALANINE; 3-TRITYLTHIO-L-ALANINE; CYSTEINE; DRUG DERIVATIVE; MECYSTEINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CONFORMATION; METHYLATION; SOLUTION AND SOLUBILITY; SYNTHESIS;

COMBINATORIAL CHEMISTRY TECHNIQUES; CYSTEINE; METHYLATION; MOLECULAR CONFORMATION; SOLUTIONS;

EID: 38849159888     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc7001588     Document Type: Article

References (43)

1. Wenger, R. M. Angew. Chem., Int. Ed. Engl. 1985, 24, 77-85.
2. Angell, Y. M.; Thomas, T. L.; Flentke, G. R.; Rich, D. H. J. Am. Chem. Soc. 1995, 117, 7279-7980.
3. Raman, P.; Stokes, S. S.; Angell, Y. M.; Flentke, G. R.; Rich, D. H. J. Org. Chem. 1998, 63, 5734-5735.
4. Davidson, B. S. Chem. Rev. 1993, 93, 1771-1791.
5. Fusetani, N.; Matsunaga, S. Chem. Rev 1993, 93, 1793-1806.
6. Wipf, P. Chem. Rev. 1995, 95, 2115-2134.
7. Hamada, Y.; Shioiri, T. Chem. Rev. 2005, 105, 4441-1482.
8. Dawson, S.; Malkinson, J. P.; Paumier, D.; Searcey, M. Nat. Prod. Rep. 2007, 24, 109-126.
9. Cruz, M.; Tusell, J. M.; Grillo-Bosch, D.; Albericio, F.; Serratosa, J.; Rabanal, F.; Giralt, E. J. Pept. Res. 2004, 63, 324-328.
10. Hughes, E.; Burke, R. M.; Doig, A. J. J. Biol. Chem. 2000, 275, 25109-25115.
11. Dechantsreiter, M. A.; Planker, E.; Mathae, B.; Lohof, E.; Hoelzemann, G.; Jonczyk, A.; Goodman, S. L.; Kessler, H. J. Med. Chem. 1999, 42, 3033-3040.
12. Nabors, L. B.; Mikkelsen, T.; Rosenfeld, S. S.; Hochberg, F.; Akella, N. S.; Fisher, J. D.; Cloud, G. A.; Zhang, Y.; Carson, K.; Wittemer, S. M.; Colevas, A. D.; Grossman, S. A. J. Clin. Oncol. 2007, 25, 1651-1657.
13. Kaiser, E. T.; Kézdy, F. J. Annu. Rev. Biophys. Biophys. Chem. 1987, 16, 561-581.
14. Teixidó, M.; Belda, I.; Zurita, E.; Llora, X.; Fabre, M.; Vilaró, S.; Albericio, F.; Giralt, E. J. Pept. Sci, 2005, 11, 789-804.
15. Hogg, P. J. Trends Biochem. Sci 2003, 28, 210-214.
16. Creighton, T. E. In Frontiers in Molecular Biology: Mechanisms of Protein Folding, 2nd ed.; Pain, R. H., Ed.; Oxford University Press: Oxford, UK, 2000; Vol. 32, pp 250-278.
17. Dobson, C. M. Nature 2003, 426, 884-890.
18. Kessler, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 512-523.
19. Rizo, J.; Gierasch, L. M. Annu. Rev. Biochem. 1992, 61, 387-418.
20. Romero, F.; Espliego, F.; Pérez Baz, J.; García de Quesada, T.; Grávalos, D.; De la Calle, F.; Fernández-Puentes, J. L. J. Antibiot. 1997, 50, 734-737.
21. Pérez Baz, J.; Cañedo, L. M.; Fernández Puentes, J. L. J. Antibiot. 1997, 50, 738-741.
22. Blondeau, P.; Berse, C.; Gravel, D. Can. J. Chem. 1967, 45, 49-52.
23. Aurelio, L.; Brownlee, R. T. C.; Hughes, A. B. Chem. Rev. 2004, 104, 5823-5846.
24. Biron, E.; Kessler, H. J. Org. Chem. 2005, 70, 5183-5189.
25. Di Gioia, M. L.; Leggio, A.; Liguori, A.; Perri, F. J. Org. Chem. 2007, 72, 3723-3728.
26. Merryman, C.; Green, R. Chem. Biol. 2004, 11, 575-582.
27. Yang, L.; Chiu, K. Tetrahedron Lett. 1997, 38, 7307-7310.
28. Miller, S. C.; Scanlan, T. S. J. Am. Chem. Soc. 1997, 119, 2301-2302.
29. Biron, E.; Chatterjee, J.; Kessler, H. J. Pept. Sci. 2006, 12, 213-219.
30. Although, the N-Methylation in the solid phase could be very convenient for the most part of the amino acids and/or peptides, it is not totally convenient for the preparation of complex molecules such as the thiocoraline family or some of the Cys derivatives. For instance, in this case, solid-phase methylation of the Cys(Me) using the nosyl strategy led to the didehydroalanine formation (unpublished results).
31. Freidinger, R. M.; Hinkle, J. S.; Perlow, D. S.; Arison, B. H. J. Org. Chem. 1983, 48, 77-81.
32. Ben-Ishai, D. J. Am. Chem. Soc. 1957, 79, 5736-5738.
33. Itoh, M. Chem. Pharm. Bull. 1969, 17, 1679-1681.
34. Aurelio, A.; Brownlee, R. T. C.; Hughes, A. B.; Sleebs, B. E. Aus. J. Chem. 2000, 53, 425-433.
35. Aurelio, A.; Box, J. S.; Brownlee, R. T. C.; Hughes, A. B.; Sleebs, M. M. J. Org. Chem. 2003, 68, 2652-2667.
36. Spengler, J.; Boettcher, C.; Albericio, F.; Burger, K. Chem. Rev. 2006, 106, 4728-1746.
37. Garcia-Martin, F.; Bayó-Puxan, N.; Cruz, L. J.; Albericio, F. QSAR Comb. Sci. 2007, 26, 1027-1035.
38. Rudolph, J.; Theis, H.; Hanke, R.; Endermann, R.; Johannsen, L.; Geschke, F. J. Med. Chem. 2001, 44, 619-626.
39. Singh, P. R.; Rajopadhye, M.; Clark, S. L.; Williams, N. E. Tetrahedron Lett. 1996, 37, 4117-4120.
40. Engebretsen, M.; Agner, E.; Sandosham, J.; Fischer, P. M. J. Pept. Res. 1997, 49, 341-346.
41. Patel, H. M.; Tao, J.; Walsh, C. T. Biochemistry 2003, 42, 10514-10527.
42. Tulla-Puche, J.; Bayó-Puxan, Moreno, J. A.; Francesch, A. M.; Cuevas, C.; Alvarez, M.; Albericio, F. J. Am. Chem. Soc. 2007, 129, 5322-5323.
43. IUPAC - IUB Commission of Biochemical Nomenclature. J. Biol. Chem. 1982, 247, 977-983.