Amine capture strategy for peptide bond formation by means of quinolinium thioester salts

Journal of the American Chemical Society

Volumn 127, Issue 45, 2005, Pages 15668-15669

  Leleu, Stéphane ^a   Penhoat, Maël ^a   Bouet, Alexis ^a   Dupas, Georges ^a   Papamicaël, Cyril ^a   Marsais, Francis ^a   Levacher, Vincent ^a  

^a Normandie Université   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; ESTER; PEPTIDE; QUINOLINE DERIVATIVE; THIOESTER;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHROMATOGRAPHY; CONTROLLED STUDY; MODEL; PEPTIDE SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET SPECTROSCOPY;

AMINES; PEPTIDES; QUINOLINIUM COMPOUNDS; SALTS; SULFURIC ACID ESTERS;

EID: 27844591232     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja054775p     Document Type: Article

References (16)

1. Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149.
2. For illustrative examples of convergent approaches by coupling of protected peptide segments, see: (a) Barlos, K.; Gatos, D.; Schäfer, W. Angew. Chem., Int. Ed. Engl. 1991, 30, 590.
3. (b) Hendrix, J. C.; Lansbury, P. T. J. Org. Chem. 1992, 57, 3421.
4. (c) Lyle, T. A.; Brady, S. F.; Cicarrone, T. M.; Colton, C. D.; Paleveda, W. J.; Veber, D. F.; Nutt, R. F. J. Org. Chem. 1987, 52, 3752.
5. For leading references on fragment peptide coupling by prior chemical ligation, see: (a) Coltart, D. M. Tetrahedron 2000, 56, 3449.
6. (b) Yeo, D. S. Y.; Srinivasan, R.; Chen, G. Y. J.; Yao, S. Q. Chem.-Eur. J. 2004, 10, 4664.
7. (c) Kent, S. J. Pept. Sci. 2003, 9, 574.
8. (a) Kemp, D. S. Biopolymers 1981, 20, 1793.
9. (b) Kemp, D. S.; Roberts, D.; Hoyng, C.; Grattan, J.; Vellaccio, F.; Reczek, J. In Peptides: Chemistry, Structures and Biology, Walter, R., Ed.; Ann Arbor Science: Ann Arbor, MI, 1975; p. 295.
10. The reversible nature of these additions has already been sporadically investigated by us and others, in view of developing new nucleophile- transferring agents. (a) Leleu, S.; Papamicaël, C.; Marsais, F.; Dupas, G.; Levacher, V. Tetrahedron: Asymmetry 2004, 15, 3919.
11. (b) Kellog, R. M. Angew. Chem., Int. Ed. Engl. 1984, 23, 782.
12. (c) Mashraqui, S. H.; Kellog, R. M. J. Am. Chem. Soc. 1983, 105, 7792.
13. The thioester group has already been widely used in native chemical ligation by means of a prior thiol capture strategy; see ref 3.
14. For leading references on safety-catch linker used in solid-phase peptide synthesis, see: (a) Backes, B. J.; Virgilio, A. A.; Ellman, J. A. J. Am. Chem. Soc. 1994, 116, 11171.
15. (b) Backes, B. J.; Virgilio, A. A.; Ellman, J. A. J. Am. Chem. Soc. 1996, 118, 3955.
16. (c) Bourne, G. T.; Golding, S. W.; McGeary, R. P.; Meutermans, W. D. F.; Jones, A.; Marshall, G. R.; Alewood, P. F.; Smythe, M. L. J. Org. Chem. 2001, 66, 7706.