Peptide ligations accelerated by N-terminal aspartate and glutamate residues

Organic Letters

Volumn 13, Issue 18, 2011, Pages 4770-4773

  Thomas, Gemma L ^a   Hsieh, Yves S Y ^a   Chun, Candy K Y ^a   Cai, Zheng Li ^a   Reimers, Jeffrey R ^a   Payne, Richard J ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIDIABETIC AGENT; ASPARTIC ACID; ESTER; EXENDIN 4; GLUTAMIC ACID; PEPTIDE; THIOL DERIVATIVE; VENOM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ASPARTIC ACID; CATALYSIS; ESTERS; GLUTAMIC ACID; HYPOGLYCEMIC AGENTS; MOLECULAR STRUCTURE; PEPTIDES; STEREOISOMERISM; SULFHYDRYL COMPOUNDS; VENOMS;

EID: 80052771002     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2017356     Document Type: Article

References (47)

1. Dawson, P. E.; Kent, S. B. H. Annu. Rev. Biochem. 2000, 69, 92
2. Davis, B. G. Chem. Rev. 2002, 102, 579
3. Macmillan, D. Angew Chem., Int. Ed. 2006, 45, 7668
4. Hackenberger, C. P. R.; Schwarzer, D. Angew. Chem., Int. Ed. 2008, 47, 10030
5. Dirksen, A.; Dawson, P. E. Curr. Opin. Chem. Biol. 2008, 12, 760
6. Kent, S. B. H. Chem. Soc. Rev. 2009, 38, 338
7. Kan, C.; Danishefsky, S. J. Tetrahedron 2009, 65, 9047
8. Payne, R. J.; Wong, C.-H. Chem. Commun. 2010, 46, 21
9. Tiefenbrunn, T. K.; Dawson, P. E. Biopolymers 2010, 94, 95
10. Yuan, Y.; Chen, J.; Wan, Q. A.; Wilson, R. M.; Danishefsky, S. J. Biopolymers 2010, 94, 373
11. Kumar, K. S. A.; Brik, A. J. Pept. Sci. 2010, 16, 524
12. Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. H. Science 1994, 266, 776
13. Hackeng, T. M.; Griffin, J. H.; Dawson, P. E. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 10068
14. Crich, D.; Banerjee, A. J. Am. Chem. Soc. 2007, 129, 10064
15. Haase, C.; Rohde, H.; Seitz, O. Angew. Chem., Int. Ed. 2008, 47, 6807
16. Chen, J.; Wan, Q.; Yuan, Y.; Zhu, J.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2008, 47, 8521
17. Yang, R. L.; Pasunooti, K. K.; Li, F. P.; Liu, X. W.; Liu, C. F. J. Am. Chem. Soc. 2009, 131, 13592
18. Harpaz, Z.; Siman, P.; Kumar, K. S. A.; Brik, A. ChemBioChem 2010, 11, 1232
19. Chen, J.; Wang, P.; Zhu, J. L.; Wan, Q.; Danishefsky, S. J. Tetrahedron 2010, 66, 2277
20. Rohde, H.; Seitz, O. Biopolymers 2010, 94, 551
21. Blake, J. Int. J. Pept. Prot. Res. 1981, 17, 273
22. Aimoto, S. Biopolymers 1999, 51, 247
23. Hojo, H.; Matsumoto, Y.; Nakahara, Y.; Ito, E.; Suzuki, Y.; Suzuki, M.; Suzuki, A. J. Am. Chem. Soc. 2005, 127, 13720
24. Chen, G.; Wan, Q.; Tan, Z. P.; Kan, C.; Hua, Z. H.; Ranganathan, K.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2007, 46, 7383
25. Payne, R. J.; Ficht, S.; Greenberg, W. A.; Wong, C.-H. Angew. Chem., Int. Ed. 2008, 47, 4411
26. Yuan, Y.; Chen, J.; Wan, Q.; Tan, Z. P.; Chen, G.; Kan, C.; Danishefsky, S. J. J. Am. Chem. Soc. 2009, 131, 5432
27. Tan, Z. P.; Shang, S. Y.; Halkina, T.; Yuan, Y.; Danishefsky, S. J. J. Am. Chem. Soc. 2009, 131, 5424
28. Kemp, D. S.; Carey, R. I. J. Org. Chem. 1993, 58, 2216
29. Brik, A.; Ficht, S.; Yang, Y.-Y.; Bennett, C. S.; Wong, C.-H. J. Am. Chem. Soc. 2006, 128, 15026
30. Lutsky, M.-Y.; Nepomniaschiy, N.; Brik, A. Chem. Commun. 2008, 1229
31. Dheur, J.; Ollivier, N.; Melnyk, O. Org. Lett. 2011, 13, 1560
32. Thomas, G. L.; Payne, R. J. Chem. Commun. 2009, 4260
33. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B. Gaussian 09, Revision A.02; Gaussian, Inc., Pittsburgh, PA, 2009.
34. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
35. Kendall, R. A.; Dunning, T. H., Jr.; Harrison, R. J. J. Chem. Phys. 1992, 96, 6796
36. Tomasi, J.; Persico, M. Chem. Rev. 1994, 94, 2027
37. Ho, J.; Klamt, A.; Coote, M. L. J. Phys. Chem.A 2010, 114, 13442
38. Hupe, D. J.; Jencks, W. P. J. Am. Chem. Soc. 1977, 99, 451
39. Wang, C.; Guo, Q.-X.; Fu, Y. Chem. Asian J. 2011, 6, 1241
40. Garel, J.; Tawfik, D. S. Chem.-Eur. J. 2006, 12, 4144
41. Eng, J.; Kleinman, W. A.; Singh, L.; Singh, G.; Raufman, J. P. J. Biol. Chem. 1992, 267, 7402
42. Furman, B. L. Toxicon 2011, DOI: 10.1016/j.toxicon.2010.12.016.
43. Wang, P.; Miranda, L. P. Int. J. Pept. Res. Ther. 2005, 11, 117
44. Ficht, S.; Payne, R. J.; Guy, R. T.; Wong, C.-H. Chem.-Eur. J. 2008, 14, 3620
45. Yang, Y. Y.; Ficht, S.; Brik, A.; Wong, C.-H. J. Am. Chem. Soc. 2007, 129, 7690
46. Ajish Kumar, K. S.; Harpaz, Z.; Haj-Yahya, M.; Brik, A. Bioorg. Med. Chem. Lett. 2009, 19, 3870
47. Thompson, R. E.; Jolliffe, K. A.; Payne, R. J. Org. Lett. 2011, 13, 680