Synthesis of a symmetric branched peptide. Assembly of a cyclic peptide on a small tetraacetate template

(Note: The full text of this document is currently only available in the PDF Version )

Chuan-Fa Liu and James P. Tam


Abstract

A method for the synthesis of a symmetric peptide dendrimer (MW 8685.0) by assembling four copies of an unprotected Cys-containing cyclic peptide via Michael addition onto a small organic template, pentaerythritol tetraacrylate, is described.


References

  1. J. P. Tam, Proc. Natl. Acad. Sci. USA, 1988, 85, 54 099.
  2. J. P. Tam and J. C. Spetzler, Biomed. Pept. Proteins Nucleic Acids, 1995, 1, 123 Search PubMed.
  3. M. Mutter and S. Vuilleumier, Angew. Chem., Int. Ed. Engl., 1989, 28, 535 CrossRef.
  4. M. Montal, M. S. Montal and J. M. Tomich, Proc. Natl. Acad. Sci. USA, 1990, 87, 6929 CAS.
  5. K. Sheldon, D. Liu, J. Ferguson and J. Gariepy, Proc. Natl. Acad. Sci. USA, 1995, 92, 2056 CAS.
  6. T. Sasaki and E. T. Kaiser, J. Am. Chem. Soc., 1989, 111, 380 CrossRef CAS.
  7. B. C. Gibb, A. R. Mezo and J. C. Sherman, Tetrahedron Lett., 1995, 36, 7587 CrossRef CAS.
  8. M. Goodman, Y. B. Feng, G. Melacini and J. P. Taulane, J. Am. Chem. Soc., 1996, 118, 5156 CrossRef CAS.
  9. (a) Y.-A. Lu, P. Clavijo, M. Galantino, Z.-Y. Shen, W. Liu and J. P. Tam, Immunology, 1991, 73, 249; (b) T. Kitagawa and T. Aikawa, J. Biochem., 1976, 79, 233 Search PubMed; (c) D. G. McCafferty, C. A. Slate, B. M. Nakhle, H. D. Graham, T. L. Austell, R. W. Vachet, B. H. Mulis and B. W. Erickson, Tetrahedron, 1995, 51, 9859 CrossRef CAS.
  10. C. F. Liu and J. P. Tam, J. Am. Chem. Soc., 1994, 116, 4149 CrossRef CAS; C. F. Liu and J. P. Tam, J. Am. Chem. Soc., 1996, 118, 307 CrossRef CAS.
  11. P. E. Dawson and S. B. H. Kent, J. Am. Chem. Soc., 1994, 116, 30 CrossRef.
  12. J. P. Tam, Y.-A. Lu and J. Shao, Proc. Natl. Acad. Sci. USA, 1995, 92, 12 485 CAS.
  13. K. Rose, J. Am. Chem. Soc., 1994, 116, 30 CrossRef.
  14. J. Shao and J. P. Tam, J. Am. Chem. Soc., 1955, 117, 3893.
  15. C.-F. Liu, C. Rao and J. P. Tam, Tetrahedron Lett., 1996, 37, 933 CrossRef CAS.
  16. P. Botti, T. D. Pallin and J. P. Tam, J. Am. Chem. Soc., 1966, 118, 10 018 CrossRef.
  17. L. Zhang and J. P. Tam, J. Am. Chem. Soc., 1997, in the press Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.