Letters in Peptide Science

, Volume 5, Issue 2–3, pp 227–233 | Cite as

Stereoselective routes towards the synthesis of unusual bis(amino acids) and cyclic amino acids

  • Kjell Undheim
Article

Summary

Stereoselective syntheses are described of bridged bis(glycines) as conformationally constrained substitutes for cystine, and of cyclic α-amino acids where the α-carbon of the amino acid is part of a five-, six- or seven-membered ring which may hold a hydroxy group as a threonine analogue.

Key words

bis(alanines) bis(glycines) bridged amino acids constrained amino acids constrained serines cystine substitutes 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.a.
    Goodman, M. and Shao, H., Pure Appl. Chem., 68 (1996) 1303 and references therein.Google Scholar
  2. 1.b.
    Degrado, W.F., Adv. Protein Chem., 39 (1988) 51 and references therein.PubMedCrossRefGoogle Scholar
  3. 2.a.
    Obrecht, D., Abrecht, C., Altorfer, M., Bohdal, U., Grieder, A., Kleber, M., Pfyffer, P. and Müller, K. Helv. Chim. Acta, 79 (1996) 1315 and references therein.CrossRefGoogle Scholar
  4. 2.b.
    Liu, W., Ray, P. and Benezra, S.A., J. Chem. Soc. Perkin Trans.1, (1995) 553 and references therein.CrossRefGoogle Scholar
  5. 3.a.
    Hammer, K. and Undheim, K., Tetrahedron, 53 (1997) 2309.CrossRefGoogle Scholar
  6. 3.b.
    Hammer, K. and Undheim, K., Tetrahedron, 53 (1997) 5925.CrossRefGoogle Scholar
  7. 3.c.
    Hammer, K. and Undheim, K., Tetrahedron, 53 (1997) 10603.CrossRefGoogle Scholar
  8. 3.d.
    Møller, B.S. and Undheim, K., unpublished.Google Scholar
  9. 4.a.
    Schöllkopf, U., Tetrahedron, 39 (1983) 2085.CrossRefGoogle Scholar
  10. 4.b.
    Schwab, P., Grubbs, R.H. and Ziller, J.W., J. Am. Chem. Soc., 118 (1996) 100 and references therein.CrossRefGoogle Scholar
  11. 4.c.
    Evans, D.A., Britton, T.C., Ellman, J.A. and Dorow, R.L., J. Am. Chem. Soc., 112 (1990) 4011.CrossRefGoogle Scholar
  12. 5.a.
    Efskind, J., Benneche, T. and Undheim, K., Acta Chem. Scand., 51 (1997) 942.Google Scholar
  13. 5.b.
    Kremminger, P. and Undheim, K., Tetrahedron, 53 (1997) 6925.CrossRefGoogle Scholar
  14. 6.a.
    Møller, B.S., Benneche, T. and Undheim, K., Tetrahedron, 52 (1996) 8807.CrossRefGoogle Scholar
  15. 6.b.
    Møller, B.S. and Undheim, K., unpublished.Google Scholar
  16. 7.
    Hammer, K., Hope, H., Benneche, T. and Undheim, K., Acta Chem. Scand., 51 (1997) 392.CrossRefGoogle Scholar
  17. 8.
    Falck-Pedersen, M.L. and Undheim, K., Tetrahedron, 52 (1996) 7761.CrossRefGoogle Scholar
  18. 9.
    Neset, S., Hope, H. and Undheim, K., Tetrahedron, 53 (1997) 10459.CrossRefGoogle Scholar
  19. 10.
    Undheim, K. and Solbakken, M., PCT Int. Appl. WO 93 24,522; Chem. Abstr., 121 (1994) 281231e.Google Scholar
  20. 11.
    Rødbotten, S., Benneche, T. and Undheim, K., Acta Chem. Scand., 51 (1997) 873.Google Scholar

Copyright information

© Kluwer Academic Publishers 1998

Authors and Affiliations

  • Kjell Undheim
    • 1
  1. 1.Department of ChemistryUniversity of OsloOsloNorway

Personalised recommendations