Identification of coupling conditions proceeding with low C-terminal epimerization during the assembly of fully protected backbone-substituted peptide segments

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 11, 1996, Pages 1219-1225

  Quibell, Martin ^a,c   Packman, Leonard C ^b   Johnson, Tony ^a,c  

^a MRC LABORATORY OF MOLECULAR BIOLOGY   (United Kingdom)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^c Peptide Therapeutics Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542735060     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19960001219     Document Type: Article

References (33)

1. E. Atherton, E. Brown, G. Priestly, R. C. Sheppard and B. J. Williams, in Peptides: Synthesis, Structure, Function. Proceedings of the 7th American Peptide Symposium, ed. D. H. Rich and E. Gross, Pierce Chemical Company, Rockford, Illinois, 1981, pp. 163-175.
2. H. Benz, Synthesis, 1994, 337.
3. P. Lloyd-Williams, F. Albericio and E. Giralt, Tetrahedron, 1993, 49, 11 065.
4. B. Riniker, A. Florsheimer, H. Fretz, P. Sieber and B. Kamber, Tetrahedron, 1993, 49, 9307.
5. K. Barlos, D. Gatos and W. Schafer, Angew. Chem., Int. Ed. Engl., 1991, 30, 590.
6. H. Yajima and N. Fujii, J. Chem. Soc., Perkin Trans. 1, 1981, 789.
7. E. Giralt, F. Albericio, I. Dalcol, G. Margarida, P. Lloyd-Williams and F. Rabanal, in Innovations and Perspectives in Solid Phase Synthesis, Third International Symposium, ed. R. Epton, Mayflower Worldwide Limited, Birmingham, England, 1994, pp. 51-60.
8. N. L. Benoiton, in The Peptides: Analysis, Synthesis, Biology, ed. E. Gross and J. Meienhofer, Acedemic Press, 1983, vol. 5, p. 217.
9. N. L. Benoiton and K. Kuroda, Int. J. Pept. Protein Res., 1981, 17, 197.
10. C. Toniolo, G. M. Bonora and W. M. M. Schaaper, Int. J. Pept. Protein Res., 1984, 23, 389.
11. C. Toniolo, G. M. Bonora, E. P. Heimer and A. M. Felix, Int. J. Pept. Protein Res., 1987, 30, 232.
12. R. C. de L. Milton, S. F. C. Milton and P. A. Adams, J. Am. Chem. Soc., 1990, 112, 6039.
13. C. H. Hyde, T. Johnson, D. Owen, M. Quibell and R. C. Sheppard, in Innovations and Perspectives in Solid Phase Synthesis, Third International Symposium, ed. R. Epton, Mayflower Worldwide Limited, Birmingham, England, 1994, pp. 29-38.
14. T. Johnson, M. Quibell, D. Owen and R. C. Sheppard, J. Chem. Soc., Chem. Commun., 1993, 369.
15. C. Hyde, T. Johnson, D. Owen, M. Quibell and R. C. Sheppard, Int. J. Pept. Protein Res., 1994, 43, 431.
16. M. Quibell, T. Johnson and W. G. Turnell, Biomed. Pept., Proteins Nucleic Acids, 1995, 1, 3.
17. M. Quibell and T. Johnson, in Peptides 1994, Proceedings of the 23rd European Peptide Symposium, ed. H. L. S. Maia, ESCOM Science Publishers B. V., Leiden, Netherlands, 1995, pp. 173-174.
18. M. Quibell, L. C. Packman and T. Johnson, J. Am. Chem. Soc., 1995, 117, 11 656.
19. A. C. Haver and D. D. Smith, in Peptides 1994, Proceedings of the 23rd European Peptide Symposium, ed. H. L. S. Maia, ESCOM Science Publishers B.V., Leiden, Netherlands, 1995, pp. 199-200.
20. N. L. Benoiton, Y. C. Lee and F. M. F. Chen, in Peptides 1994, Proceedings of the 23rd European Peptide Symposium, ed. H. L. S. Maia, ESCOM Science Publishers B.V., Leiden, Netherlands, 1995, pp. 203-204.
21. I. J. Galpin, A. K. Mohammed and A. Patel, Tetrahedron, 1988, 44, 1685.
22. L. A. Carpino, D. Sadat-Aalaee, H. G. Chao and R. H. DeSelms, J. Am. Chem. Soc., 1990, 112, 9561.
23. D. S. Kemp, in The Peptides: Analysis, Synthesis, Biology, ed. E. Gross and J. Meienhofer, Academic Press, vol. 1, 1979, pp. 315-383.
24. J. Kovacs, in The Peptides: Analysis, Synthesis, Biology, ed. E. Gross and J. Meienhofer, Academic Press, 1980, vol. 2, pp. 485-539.
25. T. Miyazawa, T. Otomatsu, T. Yamada and S. Kuwata, Int. J. Pept. Protein Res., 1992, 39, 229.
26. L. A. Carpino and A. El-Faham, J. Org. Chem., 1993, 59, 695.
27. L. A. Carpino, A. El-Faham and F. Albericio, Tetrahedron Lett., 1994, 35, 2279.
28. M. J. Churcher, C. Lamont, F. Hamy, C. Dingwall, S. M. Green, A. D. Lowe, J. G. Butler, M. J. Gait and J. Karn, J. Mol. Biol., 1993, 230, 90.
29. G. Hubener, W. Gohring, H.-J. Musiol and L. Moroder, Pept. Res., 1992, 5, 287.
30. A. Fersht, in Enzyme Structure and Mechanism, Freeman, Reading and San Francisco, 1977, p. 18.
31. E. Atherton and R. C. Sheppard, in Solid Phase Peptide Synthesis: A Practical Approach, Oxford University Press, Oxford, 1989 pp 1-203.
32. D. P. Gregory, N. Bhaskar, R. C. Sheppard and S. Singleton, in Innovations and Perspectives in Solid Phase Synthesis, Second International Symposium, ed. R. Epton, Intercept, Andover, England, 1992, pp. 391-396.
33. T. Johnson, M. Quibell and R. C. Sheppard, J. Pept. Sci., 1995, 1, 11.