Solid-phase assembly of backbone amide-protected peptide segments: An efficient and reliable strategy for the synthesis of small proteins

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 11, 1996, Pages 1227-1234

  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: 1542524949     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19960001227     Document Type: Article

References (45)

1. 1UPAC-1UB Commission on Biochemical Nomenclature, J. Biol. Chem., 1971, 247, 997.
2. R. B. Merrifield, Fed. Proc. Fed. Amer. Soc. Exp. Biol., 1962, 21, 412.
3. R. C. Sheppard, Chem. Br, 1988, 557, and references cited therein.
4. R. A. Hojo, S. Yoshimura, M. Go and S. Aimoto, Bull. Chem. Soc. Jpn., 1995, 68, 330.
5. P. E. Dawson, T. W. Muir, I. Clark-Lewis and S. B. H. Kent, Science, 1994, 266, 776.
6. D. S. Kemp and R. I. Carey, J. Org. Chem, 1993, 58, 2216.
7. 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.
8. H. Benz. Synthesis, 1994, 337.
9. P. Lloyd-Williams, F. Albericio and E. Giralt, Tetrahedron, 1993, 49, 11065.
10. B. Riniker, A. Florsheimer, H. Fretz, P. Sieber and B. Kamber, Tetrahedron, 1993, 49, 9307.
11. K. Barlos, D. Gatos, P. Frischmann and W. Schafer, in Peptides 1994, Proceedings of the 23rd European Peptide Symposium, ed. H. S. L. Maia, ESCOM Science Publishers B.V., Leiden, Netherlands. 1995, pp. 26-27.
12. K. Barlos, D. Gatos and W. Schafer, Angew. Chem., Int. Ed. Engl., 1991, 30, 590.
13. E. Bayer, N. Clausen, C. Goldammer, B. Henkel, W. Rapp and L. Zhang, in Peptides: Chemistry, Structure and Biology, Proceedings of the 13th American Peptide Symposium, ed. R. S. Hodges and J. A. Smith, ESCOM Science Publishers B.V., Leiden, Netherlands, 1995, pp. 156-158.
14. M. Narita, K. Ishikawa, J.-Y. Chen and Y. Kim, Int. J. Pept. Protein. Res., 1984, 24, 580.
15. 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.
16. H. L. Ball and P. Mascagni, in Innovations and Perspectives in Solid Phase Synthesis, Third International Symposium, ed. R. Epton, Mayflower Worldwide Limited, Birmingham, England, 1994, pp. 61-68.
17. N. L. Benoiton, in The Peptides: Analysis, Synthesis, Biology, ed. E. Gross and J. Meienhofer, Academic Press, 1983, vol. 5, p. 217.
18. N. L. Benoiton and K. Kuroda, Int. J. Pept. Protein. Res., 1981, 17, 197.
19. M. Quibell, L. C. Packman and T. Johnson, J. Am. Chem. Soc., 1995, 117, 11 656.
20. 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.
21. M. Quibell, W. G. Turnell and T. Johnson. Tetrahedron Lett., 1994, 35, 2237.
22. S. B. H. Kent, D. Alewood, P. Alewood, M. Baca, A. Jones and M. Schnollzer, in Innovations and Perspectives in Solid Phase Synthesis, Second International Symposium, ed. R. Epton, Intercept, Andover, England, 1992, p. 1.
23. E. Atherton and R. C. Sheppard, in Solid Phase Peptide Synthesis: A Practical Approach, Oxford University Press, Oxford, 1989, pp. 1-203.
24. T. Johnson, M. Quibell and R. C. Sheppard, J. Pept. Sci., 1995, 1, 11.
25. M. Quibell, L. C. Packman and T. Johnson, J. Chem. Soc., Perkin Trans. 1, 1996. preceding paper.
26. 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.
27. C. C. Zikos and N. G. Ferderigos, Tetrahedron Lett., 1994, 35, 1767.
28. D. P. Gregory, N. Bhasher, 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.
29. E. Atherton, C. J. Logan and R. C. Sheppard, J. Chem. Soc., Perkin Trans. 1, 1981, 538.
30. B. Castro, J. R. Dormay, G. Evin and C. Selve, Tetrahedron Lett., 1975, 1219.
31. G. Hubener, W. Gohring, H.-J. Musiol and L. Moroder, Pept. Res., 1992, 5, 287.
32. Unpublished results.
33. D. S. Kemp, in The Peptides: Analysis, Synthesis, Biology, ed. E. Gross and J. Meienhofer, Academic Press, vol. 1, 1979, pp. 315-383.
34. F. Marcus, Int. J. Pept. Protein, Res., 1985, 25, 542.
35. C. A. Rosen and G. N. Pavlakis, AIDS, 1990, 4, 499.
36. C. Dingwall, I. Ernberg, M. J. Gait, S. M. Green, S. Heaphy, J. Karn, A. D. Lowe, M. Singh and M. A. Skinner, EMBO J, 1990, 9, 4145.
37. M. Kraft, M. O. Westendorp, P. H. Krammer, O. Schuckert, P. Bayer, P. Rosch and R. W. Frank, in Peptides 1994, Proceedings of the 23rd European Peptide Symposium, H. L. S. Maia, ESCOM Science Publishers B. V. Leiden, Netherlands, 1995, pp. 349-350.
38. L. W. Slice, E. Codner, D. Antelman, M. Holly, B. Wegrzynski, J. Wang, V. Toome, M.-C. Hsu and C. M. Nalin, Biochemistry, 1992, 31, 12062.
39. J. Bedford, C. Hyde, T. Johnson, W. Jun, D. Owen, M. Quibell and R. C. Sheppard, Int J. Pept Protein Res., 1922, 40, 300.
40. T. Johnson, M. Quibell, D. Owen and R. C. Sheppard, J. Chem. Soc., Chem Commun., 1993, 369.
41. C. Hyde, T. Johnson, D. Owen, M. Quibell and R. C. Sheppard, Int. J. Pept. Protein Res., 1994, 43, 431.
42. R. Dolling, M. Beyerman, J. Haenel, F. Kernchen, E. Krause, M. Brudel and M. Bienert, J Chem. Soc., Chem. Commun., 1994, 853.
43. Y. Yang, W. V. Sweeney, K. Schneider, S. Thornqvist, B. T. Chait and J. T. Tam, Tetrahedron Lett., 1994, 35, 9689.
44. M. Quibell, D. Owen, L. C. Packman and T. Johnson, J. Chem. Soc., Chem. Commun., 1994, 2343.
45. J. Kovacs, in The Peptides: Analysis, Synthesis, Biology, ed. E. Gross and J. Meienhofer, Academic Press, 1980, vol. 2, pp. 485-539.