Dual kinetically controlled native chemical ligation using a combination of sulfanylproline and sulfanylethylanilide peptide

Organic Letters

Volumn 13, Issue 20, 2011, Pages 5588-5591

  Ding, Hao ^a   Shigenaga, Akira ^a   Sato, Kohei ^a   Morishita, Ko ^a   Otaka, Akira ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

NEUROMEDIN U; NEUROPEPTIDE; PEPTIDE; THIOL DERIVATIVE;

AMINO ACID SEQUENCE; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; STEREOISOMERISM; SYNTHESIS;

AMINO ACID SEQUENCE; KINETICS; MOLECULAR STRUCTURE; NEUROPEPTIDES; PEPTIDES; STEREOISOMERISM; SULFHYDRYL COMPOUNDS;

EID: 80054694198     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202316v     Document Type: Article

References (39)

1. Dawson, P.; Muir, T.; Clark-Lewis, I.; Kent, S. Science 1994, 266, 776
2. Dawson, P. E.; Kent, S. B. H. Annu. Rev. Biochem. 2000, 69, 923
3. Hackenberger, C. P. R.; Schwarzer, D. Angew. Chem., Int. Ed. 2008, 47, 10030
4. For a review of desulfurization protocol, see: Rohde, H.; Seitz, O. Peptide Sci. 2010, 94, 551
5. Yan, L. Z.; Dawson, P. E. J. Am. Chem. Soc. 2001, 123, 526
6. Bang, D.; Makhatadze, G. I.; Tereshko, V.; Kossiakoff, A. A.; Kent, S. B. Angew. Chem., Int. Ed. 2005, 44, 3852
7. Pentelute, B. L.; Kent, S. B. H. Org. Lett. 2007, 9, 687
8. Wan, Q.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2007, 46, 9248
9. Gieselman, M. D.; Xie, L.; van der Donk, W. A. Org. Lett. 2001, 3, 1331
10. Gieselman, M. D.; Zhu, Y.; Zhou, H.; Galonic, D.; van der Donk, W. A. ChemBioChem 2002, 3, 709
11. Metanis, N.; Keinan, E.; Dawson, P. E. Angew. Chem., Int. Ed. 2010, 49, 7049
12. Haase, C.; Rohde, H.; Seitz, O. Angew. Chem., Int. Ed. 2008, 47, 6807
13. Chen, J.; Wan, Q.; Yuan, Y.; Zhu, J.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2008, 47, 8521
14. Crich, D.; Banerjee, A. J. Am. Chem. Soc. 2007, 129, 10064
15. Yang, R.; Pasunooti, K. K.; Li, F.; Liu, X.-W.; Liu, C.-F. J. Am. Chem. Soc. 2009, 131, 13592
16. Pasunooti, K. K.; Yang, R.; Vedachalam, S.; Gorityala, B. K.; Liu, C.-F.; Liu, X.-W. Bioorg. Med. Chem. Lett. 2009, 19, 6268
17. Harpaz, Z.; Siman, P.; Kumar, K. S. A.; Brik, A. ChemBioChem 2010, 11, 1232
18. Tan, Z.; Shang, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2010, 49, 9500
19. Combination of ligations at Ala, Val, and Leu sites followed by desulfurization; see: Shang, S.; Tan, Z.; Danishefsky, S. J. Proc. Natl. Acad. Sci. U.S.A. 2011, 108, 5986
20. Chen, J.; Wang, P.; Zhu, J.; Wan, Q.; Danishefsky, S. J. Tetrahedron 2010, 66, 2277
21. Roelfes, G.; Hilvert, D. Angew. Chem., Int. Ed. 2003, 42, 2275
22. Brik, A.; Yang, Y.-Y.; Ficht, S.; Wong, C.-H. J. Am. Chem. Soc. 2006, 128, 5626
23. Okamoto, R.; Kajihara, Y. Angew. Chem., Int. Ed. 2008, 47, 5402
24. Thomas, G. L.; Payne, R. J. Chem. Commun. 2009, 4260
25. Hojo, H.; Ozawa, C.; Katayama, H.; Ueki, A.; Nakahara, Y.; Nakahara, Y. Angew. Chem., Int. Ed. 2010, 49, 5318
26. Ackrill, T.; Anderson, D. W.; Macmillan, D. Peptide Sci. 2010, 94, 495
27. Thomas, G. L.; Hsieh, Y. S. Y.; Chun, C. K. Y.; Cai, Z.-L.; Reimers, J. R.; Payne, R. J. Org. Lett. 2011, 13, 4770
28. Klima, H.; Tanaka, A.; Schnabel, D.; Nakano, T.; Schröder, M.; Suzuki, K.; Sandhoff, K. FEBS Lett. 1991, 289, 260
29. Shang, S.; Tan, Z.; Dong, S.; Danishefsky, S. J. J. Am. Chem. Soc. 2011, 133, 10784
30. Although Danishefsky's group utilized commercially available materials, we carried out the synthesis according to a patent. Raines, R. T.; Shoulders, M. D.; Hodges, J. A. Collagen mimics. U.S. Patent Application 20070275897, November 29, 2007. URL: http://ip.com/patapp/US20070275897.
31. Minamino, N.; Kangawa, K.; Honzawa, M.; Matsuo, H. Biochem. Biophys. Res. Commun. 1988, 156, 355
32. Aimoto, S. Peptide Sci. 1999, 51, 247-265
33. Johnson, E. C. B.; Kent, S. B. H. J. Am. Chem. Soc. 2006, 128, 6640
34. Rohde, H.; Schmalisch, J.; Harpaz, Z.; Diezmann, F.; Seitz, O. ChemBioChem 2011, 12, 1396
35. Bang, D.; Pentelute, B. L.; Kent, S. B. H. Angew. Chem., Int. Ed. 2006, 45, 3985
36. Zheng, J.-S.; Cui, H.-K.; Fang, G.-M.; Xi, W.-X.; Liu, L. ChemBioChem 2010, 11, 511
37. Tsuda, S.; Shigenaga, A.; Bando, K.; Otaka, A. Org. Lett. 2009, 11, 823
38. Sato, K.; Shigenaga, A.; Tsuji, K.; Tsuda, S.; Sumikawa, Y.; Sakamoto, K.; Otaka, A. ChemBioChem 2011, 12, 1840
39. Dheur, J.; Ollivier, N.; Vallin, A.; Melnyk, O. J. Org. Chem. 2011, 76, 3194