Application of reversible amide-bond protection to suppress peptide segment epimerisation

Tetrahedron Letters

Volumn 38, Issue 52, 1997, Pages 9047-9050

  Offer, John ^a   Johnson, Tony ^b   Quibell, Martin ^b  

^a MRC LABORATORY OF MOLECULAR BIOLOGY   (United Kingdom)

^b Peptide Therapeutics Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; PEPTIDE; SYNTHETIC PEPTIDE;

ALKYLATION; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; PROTECTION; SYNTHESIS;

EID: 0030733981     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10431-2     Document Type: Article

References (22)

1. Merrifield, R.B.; Marglin, A. In Peptides; Beyerman, H. C.; van de Linde, A.; Maasen van den Brink, W., Eds.; North-Holland publishing: Amsterdam, 1967; 85.
2. (a) Kemp, D. S. In The Peptides; Gross, E.; Meienhofer, J., Eds.; Academic Press: New York, 1979; Vol. 1, Chapter 7.
3. (b) Benoiton, N. L. In The Peptides; Gross, E.; Meienhofer, J., Eds.; Academic Press: New York, 1983; Vol. 5, Chapter 4.
4. (c) Kovacs, J. In The Peptides, Gross, E.; Meienhofer, J., Eds.; Academic Press: New York, 1980; Vol. 2, Chapter 8.
5. Quibell, M.; Packman, L. C.; Johnson, T. J. Am. Chem. Soc.; 1995, 117, 11656-11668.
6. McDermott J. R.; Benoiton, N. L. Canad. J. Chem. 1973, 51, 2562-2570.
7. Johnson, T.; Quibell, M.; Owen, D.; Sheppard, R. C. J. Chem. Soc., Chem. Commun. 1993, 369-372.
8. α-(2-hydroxy-4-methoxybenzyl) amino acids upon activation. In our experience (unpublished observations) coupling of segments containing C-terminal Hmb residues does not reach completion even on extended or repeat coupling (see Table 1).
9. Nicolas, E.; Pujades, M.; Bacardit,; Giralt, E.; Albericio, F. Tetrahedron Lett. 1997, 38, 2317-2320.
10. Quibell, M.; Packman, L. C.; Johnson, T. J. Chem. Soc., Perkin Trans. I. 1996, 1219-1225.
11. Rich, H.; Singh, J. In The Peptides, Gross, E.; Meienhofer, J., Eds.; Academic Press: New York, 1983, Vol. 1, Chapter 5.
12. Benoiton, N. L.; Lee, Y. C.; Steinaur, R.; Chen, F. M. F. Int. J. Peptide Protein Res. 1992, 40, 559-566.
13. Kenner, G. W.; McDermott, J. R.; Sheppard, R. C. J. Chem. Soc., Chem. Commun. 1971, 636-637.
14. (a) Patek, M.; Lebl, M. Collect. Czech. Chem. Commun. 1992, 57, 508-524.
15. (b) Kiso, Y.; Fukui, T.; Tanaka, S.; Kimura, T.; Akajii, K. Tetrahedron Lett. 1994, 35, 3571-3574.
16. (c) Samanen, J. M.; Brandeis, E. J. Org. Chem. 1988, 53, 561-569.
17. (d) Futaki, S.; Takashi, T.; Akita, T.; Kitagawa, K. J. Chem. Soc. Chem. Commun., 1990, 523-524.
18. Quibell, M.; Turnell, W. G. ; Johnson, T. Tetrahedron Lett. 1994, 35, 2237-2238.
19. (a) Pantlitsckho, M.; Benger, H. Monatsh. Chem., 1950, 81, 293-300.
20. (b) Traxler, J. T. J. Org. Chem. 1979, 44, 4971-4973.
21. Johnson, T.; Quibell. M.; Sheppard, R. C. J. Pept. Sci., 1995, 1, 11-25.
22. Yajima, H.; Fujii, N.; Funakoshi, S.; Watanabe, T.; Murayama, E.; Otaka, A. Tetrahedron. 1988, 44, 805-819.