Exploration of an imide capture/N,N-acyl shift sequence for asparagine native peptide bond formation

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 12, 2013, Pages 3479-3485

  Mhidia, Reda ^a   Boll, Emmanuelle ^a   Fécourt, Fabien ^b   Ermolenko, Mikhail ^b   Ollivier, Nathalie ^a   Sasaki, Kaname ^b   Crich, David ^b   Delpech, Bernard ^b   Melnyk, Oleg ^a  

^a UNIV LILLE   (France)

^b CNRS   (France)

Author keywords

Acylazide; Asparagine; Imide capture step; N,N Acyl shift; Peptide bond; Thioacid

Indexed keywords

ASPARAGINE; IMIDE;

ARTICLE; CARBOXY TERMINAL SEQUENCE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CONTROLLED STUDY; EXPLORATORY RESEARCH; MOLECULAR INTERACTION; PROTEIN BINDING; REACTION ANALYSIS; SEQUENCE ANALYSIS;

ASPARAGINE; IMIDES; MOLECULAR CONFORMATION; PEPTIDES;

EID: 84878222205     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.02.053     Document Type: Article

References (45)

1. V.R. Pattabiraman, and J.W. Bode Nature 480 2011 471
2. S. Aimoto Biopolymers 51 1999 247
3. J. Blake, and C.H. Li Proc. Natl. Acad. Sci. U.S.A. 78 1981 4055
4. J. Blake Int. J. Pept. Protein Res. 17 1981 273
5. D.M. Coltart Tetrahedron 56 2000 3449
6. S.B. Kent Chem. Soc. Rev. 38 2009 338
7. P.E. Dawson, T.W. Muir, I. Clark-Lewis, and S.B. Kent Science 266 1994 776
8. L. Raibaut, N. Ollivier, and O. Melnyk Chem. Soc. Rev. 41 2012 7001
9. N. Ollivier, J. Vicogne, A. Vallin, H. Drobecq, R. Desmet, O. El-Mahdi, B. Leclercq, G. Goormachtigh, V. Fafeur, and O. Melnyk Angew. Chem., Int. Ed. 51 2012 209
10. E. Boll, J. Dheur, H. Drobecq, and O. Melnyk Org. Lett. 14 2012 2222
11. W. Hou, X. Zhang, F. Li, and C.F. Liu Org. Lett. 13 2011 386
12. N. Ollivier, J. Dheur, R. Mhidia, A. Blanpain, and O. Melnyk Org. Lett. 12 2010 5238
13. E. Saxon, J.I. Armstrong, and C.R. Bertozzi Org. Lett. 2 2000 2141
14. B.L. Nilsson, L.L. Kiessling, and R.T. Raines Org. Lett. 2000 1939 2
15. J.W. Bode, R.M. Fox, and K.D. Baucom Angew. Chem., Int. Ed. 45 2006 1248
16. K. Sasaki, S. Aubry, and D. Crich Phosphorus, Sulfur, Silicon 186 2011 1005
17. D. Crich, and I. Sharma Angew. Chem., Int. Ed. 48 2009 2355
18. D. Crich, and I. Sharma Angew. Chem., Int. Ed. 48 2009 7591
19. J.P. Tam, Q. Yu, and Z. Miao Biopolymers 51 1999 311
20. J.P. Tam, Y.A. Lu, C.F. Liu, and J. Shao Proc. Natl. Acad. Sci. U.S.A. 92 1995 12485
21. C.-F. Liu, C. Rao, and J.P. Tam Tetrahedron Lett. 37 1996 933
22. D. Crich, and K. Sasaki Org. Lett. 11 2009 3514
23. N. Assem, A. Natarajan, and A.K. Yudin J. Am. Chem. Soc. 132 2010 10986
24. R.V. Kolakowski, N. Shangguan, R.R. Sauers, and L.J. Williams J. Am. Chem. Soc. 128 2006 5695
25. N. Shangguan, S. Katukojvala, R. Greenberg, and L.J. Williams J. Am. Chem. Soc. 125 2003 7754
26. K.N. Barlett, R.V. Kolakowski, S. Katukojvala, and L.J. Williams Org. Lett. 8 2006 823
27. R. Merkx, A.J. Brouwer, D.T. Rijkers, and R.M. Liskamp Org. Lett. 7 2005 1125
28. D.T. Rijkers, R. Merkx, C.B. Yim, A.J. Brouwer, and R.M.J. Liskamp Pept. Sci. 16 2010 1
29. R. Merkx, M.J. van Haren, D.T. Rijkers, and R.M.J. Liskamp Org. Chem. 72 2007 4574
30. X. Zhang, F. Li, X.W. Lu, and C.F. Liu Bioconjugate Chem. 20 2009 197
31. G.W. Kenner, J.R. McDermott, and R.C.J. Sheppard Chem. Soc. D: Chem. Commun. 1971 636
32. Y. Shin, K.A. Winans, B.J. Backes, S.B.H. Kent, J.A. Ellman, and C.R. Bertozzi J. Am. Chem. Soc. 121 1999 11684
33. B.J. Backes, and J.A.J. Ellman Org. Chem. 64 1999 2322
34. B.J. Backes, A.A. Virgilio, and J.A. Ellman J. Am. Chem. Soc. 118 1996 3055
35. R. Ingenito, E. Bianchi, D. Fattori, and A. Pessi J. Am. Chem. Soc. 121 1999 11369
36. R. Mhidia, N. Beziere, A. Blanpain, N. Pommery, and O. Melnyk Org. Lett. 12 2010 3982
37. A.H. Kahns, and H. Bundgaard Int. J. Pharm. 71 1991 31
38. T. Tsunoda, O. Sasaki, O. Takeuchi, and S. Itô Tetrahedron 47 1991 3925
39. P.H. Lee, S.N. Ayyampalayam, L.A. Carreira, M. Shalaeva, S. Bhattachar, R. Coselmon, S. Poole, E. Gifford, and F. Lombardo Mol. Pharm. 4 2007 498
40. J. Lutz, H.J. Musiol, and L. Moroder M. Goodman, A. Felix, L. Moroder, C. Toniolo, Houben-Weyl, Methods of Organic Chemistry, Synthesis of Peptides and Peptidomimetics Vol. E22a 2002 Georg Thieme Stuttgart 427
41. G.-M. Fang, J.-X. Wang, and L. Liu Angew. Chem., Int. Ed. 124 2012 10493
42. G.-M. Fang, Y.-M. Li, F. Shen, Y.-C. Huang, J.-B. Li, Y. Lin, H.-K. Cui, and L. Liu Angew. Chem., Int. Ed. 50 2011 7645
43. M. Raban, R. Keintz, D.P. Haritos, and J.J. Greenblatt Org. Chem. 45 1980 2672
44. M.C. Etter, and S.M. Reutzel J. Am. Chem. Soc. 113 1991 2586
45. W. Amelung, and S. Brodowski Anal. Chem. 74 2002 3239