Internal cysteine accelerates thioester-based peptide ligation

European Journal of Organic Chemistry

Volumn , Issue 13, 2009, Pages 2096-2101

  Haase, Christian ^a   Seitz, Oliver ^a  

^a HUMBOLDT UNIVERSITY   (Germany)

Author keywords

Coupling; Macrocycles; Peptides; Synthetic methods; Thioester

Indexed keywords

EID: 66149141721     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900024     Document Type: Article

References (46)

1. a) P. E. Dawson, T. W. Muir, I. Clark-Lewis, S. B. H. Kent, Science 1994, 266, 776-779;
2. b) T. Wieland, E. Bokelmann, L. Bauer, U. Lang, H. Lau, Justus Liebigs Ann. Chem. 1953, 583, 129-149;
3. c) C. P. R. Hackenberger, D. Schwarzer, Angew. Chem. 2008, 120, 10182-10228; Angew. Chem. Int. Ed. 2008, 47, 10030-10074;
4. d) B. L. Nilson, M. B. Soellner, R. T. Raines, Annu. Rev. Biophys. Biomol. Struct. 2005, 34,91-118.
5. http://www.ebi.ac.uk/swissprot/sptr-stats/index.html.
6. a) L. Z. Yan, P. E. Dawson, J. Am. Chem. Soc. 2001, 123, 526-533;
7. b) B. L. Pentelute, S. B. H. Kent, Org. Lett. 2007, 9, 687-690;
8. c) Q. Wan, S. J. Danishefsky, Angew. Chem. 2007, 119, 9408-9412;
9. Angew. Chem. Int. Ed. 2007, 46, 9248-9252.
10. R. Okamoto, Y. Kajihara, Angew. Chem. 2008, 120, 5482-5486;
11. Angew. Chem. Int. Ed. 2008, 47, 5402-5406.
12. D. Macmillan, C. R. Bertozzi, Angew. Chem. 2004, 116, 1379-1383;
13. Angew. Chem. Int. Ed. 2004, 43, 1355-1359.
14. a) A. Saporito, D. Marasco, A. Chambery, P. Botti, S. M. Monti, C. Pedone, M. Ruvo, Biopolymers 2006, 83, 508-518;
15. b) J. P. Tam, Q. T. Yu, Biopolymers 1998, 46, 319-327;
16. c) K. Pachamuthu, R. R. Schmidt, Synlett 2003, 659-662.
17. a) P. Botti, S. Tchertchian, 2006, WO 2006/133962;
18. b) D. Crich, A. Banerjee, J. Am. Chem. Soc. 2007, 129, 10064-10065.
19. C. Haase, H. Rohde, O. Seitz, Angew. Chem. 2008, 120, 6912-6915;
20. Angew. Chem. Int. Ed. 2008, 47, 6807-6810.
21. J. Chen, Q. Wan, Y. Yuan, J. Zhu, S. J. Danishefsky, Angew. Chem. 2008, 120, 8649-8652;
22. Angew. Chem. Int. Ed. 2008, 47, 8521-8524.
23. a) L. E. Canne, S. J. Bark, S. B. H. Kent, J. Am. Chem. Soc. 1996, 118, 5891-5896;
24. b) J. Offer, P. E. Dawson, Org. Lett. 2000, 2,23-26;
25. c) P. Botti, M. R. Carrasco, S. B. H. Kent, Tetrahedron Lett. 2001, 42, 1831-1833;
26. d) C. Marinzi, S. J. Bark, J. Offer, P. E. Dawson, Bioorg. Med. Chem. 2001, 9, 2323-2328;
27. e) T. Kawakami, K. Akaji, S. Aimoto, Org. Lett. 2001, 3, 1403-1405;
28. f) J. Offer, C. N. C. Boddy, P. E. Dawson, J. Am. Chem. Soc. 2002, 124, 4642-4646;
29. g) C. Marinzi, J. Offer, R. Longhi, P. E. Dawson, Bioorg. Med. Chem. 2004, 12, 2749-2757;
30. h) G. Chen, J. D. Warren, J. Chen, B. Wu, Q. Wan, S. J. Danishefsky, J. Am. Chem. Soc. 2006, 128, 7460-7462.
31. a) A. Brik, S. Ficht, Y. Y. Yang, C. S. Bennett, C. H. Wong, J. Am. Chem. Soc. 2006, 128, 15026-15033;
32. b) A. Brik, Y. Y Yang, S. Ficht, C. H. Wong, J. Am. Chem. Soc. 2006, 128, 5626-5627;
33. c) R. J. Payne, S. Ficht, S. Tang, A. Brik, Y. Y. Yang,D. A. Case,C. H.Wong, J. Am. Chem. Soc. 2007, 129, 13527-13536;
34. d) Y. Y. Yang, S. Ficht, A. Brik, C. H. Wong, J. Am. Chem. Soc. 2007, 129, 7690-7701;
35. e) S. Ficht, R. J. Payne, A. Brik, C. H. Wong, Angew. Chem. 2007,119, 6079-6083;
36. An-gew. Chem. Int. Ed. 2007, 46, 5975-5979.
37. M. Y. Lutsky, N. Nepomniaschiy, A. Brik, Chem. Commun. 2008, 1229-1231.
38. T. M. Hackeng, J. H. Griffin, P. E. Dawson, Proc. Natl. Acad. Sci. USA 1999, 96, 10068-10073.
39. M. Villain, H. Gaertner, P. Botti, Eur. J. Org. Chem. 2003, 3267-3272.
40. M. C. deKoning, D. V. Filippov, G. A. vanderMarel, J. H. van Boom, M. Overhand, Eur. J. Org. Chem. 2004, 850-857.
41. R.J. Payne, S. Ficht, W. A. Greenberg, C. H. Wong, Angew. Chem. 2008, 120, 4483-4487;
42. Angew. Chem. Int. Ed. 2008, 47, 4411 -4415.
43. E. C. B. Johnson, S. B. H. Kent, J. Am. Chem. Soc. 2006, 128, 6640-6646.
44. J. Blake, C. H. Li, Proc. Natl. Acad. Sci. USA 1981, 78, 4055-4058.
45. H. Hojo, S. Aimoto, Bull. Chem. Soc. Jpn. 1991, 64, 111-117.
46. J. S. Davies, J. Pept. Sci. 2003, 9, 471-501.