Secondary structure in oligomers of carbohydrate amino acids

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

Martin D. Smith, Timothy D. W. Claridge, George W. J. Fleet, George E. Tranter and Mark S. P. Sansom


Abstract

Short oligomeric chains of tetrahydrofuran amino acids exhibit a novel repeating β-turn type secondary structure in solution stabilised by hydrogen bonds and provide clear evidence that carbopeptoids will allow control of conformation in peptidomimetics.


References

  1. B. Iverson, Nature, 1997, 385, 114 CrossRef CAS; S. Borman, Chem. Eng. News, 1997, 32; S. H. Gellmann, Acc. Chem. Res., 1998, 31, 173 CrossRef CAS.
  2. D. Seebach and J. L. Matthews, Chem. Commun., 1997, 2015 RSC; D. W. Appella, L. A. Christianson, I. L. Karla, D. R. Powell and S. H. Gellman, J. Am. Chem. Soc., 1996, 118, 13 071 CrossRef; D. W. Appella, L. A. Christianson, D. A. Klein, D. R. Powell, X. Huang, J. J. Barchi and S. H. Gellman, Nature, 1997, 387, 381 CrossRef CAS; Y. Hamuro, S. J. Geig and A. D. Hamilton, J. Am. Chem. Soc., 1997, 119, 10 587 CrossRef CAS; D. M. Bassani, J. M. Lehn, G. Baum and D. Fenske, Angew. Chem., Int. Ed. Engl., 1997, 118, 1845 CrossRef CAS; J. C. Nelson, J. G. Saver, J. S. Moore and P. G. Wolynes, Science, 1997, 277, 1793 CrossRef CAS.
  3. K. Heyns and H. Paulsen, Chem. Ber., 1955, 88, 188 CAS; E. G. von Roedern and H. Kessler, Angew. Chem., Int. Ed. Engl., 1994, 334, 687 CrossRef; E. G. von Roedern, E. Lohof, G. Hessler, M. Hoffmann and H. Kessler, J. Am Chem. Soc., 1996, 118, 10 156 CrossRef CAS; J. P. McDevitt and P. T. Lansbury, J. Am. Chem. Soc., 1996, 118, 3818 CrossRef CAS; R. A. Goodnow, A.-R. Richou and S. Tam, Tetrahedron Lett., 1997, 38, 3195 CrossRef CAS.
  4. L. Poitout, Y. le Merrer and J.-C. Depazay, Tetrahedron Lett., 1995, 36, 6887 CrossRef CAS.
  5. E. F. Fuchs and J. Lehmann, Chem. Ber., 1975, 108, 2254 CAS.
  6. K. C. Nicolaou, H. M. Florke, G. Egan, T. Barth and V. A. Estevez, Tetrahedron Lett., 1995, 36, 1775 CrossRef CAS.
  7. Y. Suhara, J. E. K. Hildreth and Y. Ichikawa, Tetrahedron Lett., 1996, 37, 1575 CrossRef CAS; Y. Suhara, M. Izumi, M. Ichikawa, M. B. Penno and Y. Ichikawa, Tetrahedron Lett., 1997, 38, 7167 CrossRef CAS; H. P. Wessel, C. M. Mitchell, C. M. Lobato and G. Schmidt, Angew. Chem., Int. Ed. Engl., 1995, 34, 2712 CAS; S. Sabesan, Tetrahedron Lett., 1997, 38, 3127 CrossRef CAS; C. M. Timmers, J. J. Turner, C. M. Ward, G. A. van der Marcel, M. L. C. E. Kouwijzer, P. D. J. Grootenhuis and J. H. van Boom, Chem. Eur. J., 1997, 6, 920.
  8. C. Muller, E. Kitas and H. P. Wessel, J. Chem. Soc., Chem. Commun., 1995, 2425 RSC; B. Drouillat, B. Kellam, G. Dekany, M. S. Starr and I. Toth, Bioorg. Med. Chem. Lett., 1997, 17, 2247 CrossRef CAS; R. A. Goodnow, D. L. Preuss, S. Tam and W. W. McComas, Tetrahedron Lett., 1997, 38, 3199 CrossRef CAS.
  9. L. Szabo, B. L. Smith, K. D. McReynolds, A. L. Parill, E. R. Morris and J. Gervay, J. Org. Chem., 1998, 63, 1074 CrossRef CAS.
  10. M. D. Smith, D. D. Long, D. G. Marquess, T. D. W. Claridge and G. W. J. Fleet, Chem. Commun., 1998, 2039 RSC.
  11. T.-L. Hwang and J. L. Shaka, J. Magn. Reson. (B), 1993, 102, 155 Search PubMed.
  12. H. Kessler, P. Schmeider, M. Köck and M. Kurz, J. Magn. Reson., 1990, 88, 615 CAS.
  13. J. A. Smith and L. G. Pease, C. R. C. Crit. Rev. Biochem., 1980, 8, 315 Search PubMed.
  14. B. R. Brooks, J. Comput. Chem., 1983, 4, 187 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.