, Volume 38, Issue 6, pp 655–657 | Cite as

Hydrophobic properties of model compounds with peptide-like chemical environment: N-acetyl-N′-methyl-amino acid amides

  • H. J. Wynne
  • K. H. Van Buuren
  • W. Wakelkamp


Capacity factors in reversed-phase HPLC and distribution constants in octan-l-ol/water of N-acetyl-N′-methylamino acid amides have been measured as a function of temperature. The HPLC capacity factors are proposed as estimates of the hydrophobicity of the amino acid side chains.


HPLC Amide Chemical Environment Model Compound Capacity Factor 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 2.
    W. Kauzmann, Adv. Prot. Chem.14, 1 (1959).Google Scholar
  2. 3.
    C. Tanford, J. Am. chem. Soc.84, 4240 (1962).Google Scholar
  3. 4.
    J.L. Finney, B.J. Gellatly, I.C. Golton and J. Goodfellow, Biophys. J.20, 17 (1980).Google Scholar
  4. 5.
    V. Pliska., in: Perspectives in peptide chemistry, p. 221. Eds A. Eberle, R. Geiger and T. Wieland. Karger, Basel 1981.Google Scholar
  5. 6.
    I. Molnár and C. Horváth, J. Chromat.142, 623 (1977).Google Scholar
  6. 7.
    Y. Nozaki and C. Tanford, J. biol. Chem.246, 2211 (1971).Google Scholar
  7. 8.
    R.A. Klein, M.J. Moore and M.W. Smith, Biochim. biophys. Acta233, 420 (1971).Google Scholar
  8. 9.
    C. Hansch and A. Leo, Substituent constants for correlation analysis in chemistry and biology. Wiley, New York 1979.Google Scholar
  9. 10.
    V. Pliska, M. Schmidt and J.L. Fauchère, J. Chromat., in press (1981).Google Scholar
  10. 11.
    J.M. Zimmerman, N. Eliezer and R. Simha, J. theor. Biol.21, 170 (1968).Google Scholar
  11. 12.
    H. Bull and K. Breese, Archs Biochem. Biophys.161, 665 (1974).Google Scholar
  12. 13.
    H.A. Scheraga, Acc. Chem. Res.12, 7 (1979).Google Scholar
  13. 14.
    W.R. Melander, J. Stoveken and C. Horváth, J. Chromat.199, 35 (1980).Google Scholar
  14. 15.
    F.F. Cantwell and H.Y. Mohammed, Analyt. Chem.51, 218 (1979).Google Scholar
  15. 16.
    J.F.M. Kinkel, E. Tomlinson and P. Smit, Int. J. Pharmaceutics9, 121 (1981).Google Scholar
  16. 17.
    A.E. Beezer, W.H. Hunter and D.E. Storey, J. Pharm. Pharmac.32, 815 (1980).Google Scholar
  17. 18.
    P.H. Wang and E.J. Lien, J pharm. Sci.69, 662 (1980).Google Scholar
  18. 19.
    W.R. Melander, D.E. Campbell and C. Horváth, J. Chromat.158, 215 (1978).Google Scholar
  19. 20.
    C. Horváth, W.R. Melander and I. Molnár, J. Chromat.125, 129 (1976).Google Scholar
  20. 21.
    R.F. Rekker, The hydrophobic fragmental constant. Elsevier, Amsterdam 1977.Google Scholar
  21. 22.
    J.H. Rytting, S.S. Davis and T. Higuchi, J. pharm. Sci.61, 816 (1970).Google Scholar

Copyright information

© Birkhäuser-Verlag 1982

Authors and Affiliations

  • H. J. Wynne
    • 1
  • K. H. Van Buuren
    • 1
  • W. Wakelkamp
    • 1
  1. 1.Department of Pharmaceutical ChemistryUniversity of AmsterdamAmsterdam(The Netherlands)

Personalised recommendations