Formation of the Peptide Bond

  • Miklos Bodanszky

Abstract

In order to convert carboxylic acids into acylating agents their hydroxyl group must be replaced by an electron-withdrawing substituent (X) to enhance the polarization of the carbonyl group and thereby the electrophilicity of its carbon atom. Thus the nucleophilic attack by the amino group (of the amino acid to be acylated) is greatly facilitated:

Keywords

Catechol Transesterification Quinoline Dipeptide Phosphonium 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Anderson, G. W., Zimmerman, J. E., Callahan, F. M.: J. Amer. Chem. Soc. 85, 3039 (1963)CrossRefGoogle Scholar
  2. Bates, A. J., Galpin, I. J., Hallett, A., Hudson, D., Kenner, G. W., Ramage, R.: Helv. Chim. Acta 58, 688 (1975)PubMedCrossRefGoogle Scholar
  3. Belleau, D., Malek, G.: J. Amer. Chem. Soc. 90, 1651 (1968)CrossRefGoogle Scholar
  4. Bodanszky, M.: Nature 175, 685 (1955)PubMedCrossRefGoogle Scholar
  5. Boissonnas, R. A.: Helv. Chim. Acta. 34, 874 (1951)CrossRefGoogle Scholar
  6. Brenner, M., Hofer, W.: Helv. Chim. Acta 44, 1794, 1798 (1961)CrossRefGoogle Scholar
  7. Brenner, M., Zimmermann, J. P., Wehrmüller, J., Quitt, P., Photaki, I.: Helv. Chim. Acta 40, 1497 (1957)CrossRefGoogle Scholar
  8. Castro, B., Dormoy, J. R., Evin G., Selve, C.: Tetrahedron lett. 1975, 1219Google Scholar
  9. Curtius, T.: Ber. dtsch. Chem. Ges. 35, 3226 (1902)CrossRefGoogle Scholar
  10. Fischer, E.: Ber. dtsch. Chem. Ges. 36, 2094 (1903)CrossRefGoogle Scholar
  11. Fruton, J. S. in Advances in Enzymology, vol. 53 Meister, A. ed. p. 239, New York, Wiley 1982Google Scholar
  12. König, W., Geiger, R.: Chem. Ber. 103, 788, 2024, 2034 (1970)PubMedCrossRefGoogle Scholar
  13. König, W., Geiger, R.: Chem. Ber. 186, 3626 (1973)CrossRefGoogle Scholar
  14. Kovács, J., Kisfaludy, L., Ceprini, M. Q.: J. Amer. Chem. Soc. 89, 183 (1967)CrossRefGoogle Scholar
  15. Kupriszewski, G.: Rocz. Chem. 35, 595 (1961); Chem. Abstr. 55, 27121i(1961)Google Scholar
  16. Leuchs, H.: Ber. dtsch. Chem. Ges. 69, 857 (1906)CrossRefGoogle Scholar
  17. Mukaiyama, T., Ueki, M., Maruyama, H., Matsueda, R.: J. Amer. Chem. Soc. 90, 4490 (1968); ibid. 91, 1554 (1969)CrossRefGoogle Scholar
  18. Pless, J., Boissonnas, R. A.: Helv. Chim. Acta 46, 1609 (1963)CrossRefGoogle Scholar
  19. Sealock, R. W., Laskowski, M., Jr.: Biochemistry 8, 3703 (1969)PubMedCrossRefGoogle Scholar
  20. Laskowski, M. in Semisynthetic Peptides and Proteins, Offord, R. E., DiBello, C., eds. p. 263, London, Acad. Press 1978Google Scholar
  21. Schwyzer, R., Iselin, B., Feurer, M.: Helv. Chim. Acta 38, 69 (1955)CrossRefGoogle Scholar
  22. Schwyzer, R., Feurer, M., Iselin, B., Kagi, H. ibid. 38, 80 (1955)Google Scholar
  23. Schwyzer, R., Feurer, M., Iselin, B.: ibid. 38, 1067 (1955)Google Scholar
  24. Sheehan, J. C., Hess, G. P.: J. Amer. Chem. Soc. 77, 1067 (1955)CrossRefGoogle Scholar
  25. Staab, H. A.: Liebigs Ann. Chem. 609, 75 (1957)CrossRefGoogle Scholar
  26. Ugi, I. in The Peptides, vol. 2 (Gross, E., Meienhofer, J., eds.) p. 365, New York, Academic Press 1986Google Scholar
  27. Vaughan, J. R., Jr.: J. Amer. Chem. Soc. 73, 3547 (1951)CrossRefGoogle Scholar
  28. Vaughan, J. R., Osato, R. L.: J. Amer. Chem. Soc. 73, 5553 (1951)CrossRefGoogle Scholar
  29. Wieland, T., Bernhard, H.: Liebigs Ann. Chem. 572, 190 (1951)CrossRefGoogle Scholar

Additional Sources

  1. Bodanszky, M.: Active Esters in Peptide Synthesis, in The Peptides, vol. 1, Gross, E., Meienhofer, J. eds., pp. 105–196, New York, Academic Press 1979Google Scholar
  2. Meienhofer, J.: The Azide Method in Peptide Synthesis, in The Peptides, vol. 1, Gross, E., Meienhofer, J. eds., pp. 197–239, New York, Academic Press 1979Google Scholar
  3. Meienhofer, J.: The Mixed Anhydride Method of Peptide Synthesis, in The Peptides vol. 1, Gross, E., Meienhofer, J. eds., pp. 263–314, New York, Academic Press 1979Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1988

Authors and Affiliations

  • Miklos Bodanszky
    • 1
  1. 1.PrincetonUSA

Personalised recommendations