Skip to main content
SpringerLink
Log in

Synthesis, conformation, and membrane modifying properties of the trikoningin KB lipopeptaibols: Effect of hydrophobicity and chirality in position 1

  • Published:
Letters in Peptide Science Aims and scope Submit manuscript

Abstract

We synthesized by solution-phase methods thenaturally occurring, 10-amino acid residuelipopeptaibol antibiotics trikoningins KBI and KBII,and the [L-Iva1] KB analogue, in which the aminoacid in position 1 is different, with the aim atinvestigating the effect of hydrophobicity andchirality in that position. A solution conformationalanalysis, using FT–IR absorption and CD techniques,indicated that all of the three decapeptides arepredominantly helical in a membrane-mimeticenvironment. Permeability measurements showed anincrease of the activity from the [Aib1] peptideto the more hydrophobic [Iva1] peptides.Conversely, the effect of a change in chirality,obtained by replacing D-Iva1 with L-Iva, turnedout to be of minor significance.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Nagaraj, R. and Balaram, P., Acc. Chem. Res., 14 (1981) 356.

    Google Scholar 

  2. Benedetti, E., Bavoso, A., Di Blasio, B., Pavone, V., Pedone, C., Toniolo, C. and Bonora, G.M., Proc. Natl. Acad. Sci. USA, 79 (1982) 7951.

    Google Scholar 

  3. Auvin-Guette, C., Rebuffat, S., Prigent, Y. and Bodo, B., J. Am. Chem. Soc., 114 (1992) 2170.

    Google Scholar 

  4. Toniolo, C., Peggion, C., Crisma, M., Formaggio, F., Shui, X. and Eggleston, D.S., Nat. Struct. Biol., 1 (1994) 908.

    Google Scholar 

  5. Toniolo, C., Crisma, M., Formaggio, F., Peggion, C., Monaco, V., Goulard, C., Rebuffat, S. and Bodo, B., J. Am. Chem. Soc., 118 (1996) 4952.

    Google Scholar 

  6. Scrimin, P., Veronese, A., Tecilla, P., Tonellato, U., Monaco, V., Formaggio, F., Crisma, M. and Toniolo, C., J. Am. Chem. Soc., 118 (1996) 2505.

    Google Scholar 

  7. Shui, X., Eggleston, D.S., Monaco, V., Formaggio, F., Crisma, M. and Toniolo, C., In Kaumaya, P.T.P. and Hodges, R.S. (Eds.), Peptides: Chemistry, Structure and Biology, May-flower Scientific Ltd., Kingswinford, U.K., 1996, pp. 436-437.

    Google Scholar 

  8. Crisma, M., Monaco, V., Formaggio, F., Toniolo, C., George, C. and Flippen-Anderson, J.L., Lett. Pept. Sci., 4 (1997) 213.

    Google Scholar 

  9. Locardi, E., Mammi, S., Peggion, E., Monaco, V., Formaggio, F., Crisma, M., Toniolo, C., Bodo, B., Rebuffat, S., Kamphuis, J. and Broxterman, Q.B., J. Pept. Sci., 4 (1998) 389.

    Google Scholar 

  10. Monaco, V., Locardi, E., Formaggio, F., Crisma, M., Mammi, S., Peggion, E., Toniolo, C., Rebuffat, S. and Bodo, B., J. Pept. Res., 52 (1998) 261.

    Google Scholar 

  11. Auvin-Guette, C., Rebuffat, S., Vuidepot, I., Massias, M. and Bodo, B., J. Chem. Soc., Perkin Trans. 1, (1993) 249.

    Google Scholar 

  12. Fujita, T., Wada, S., Iida, A., Nishimura, T., Kanai, M. and Toyama, N., Chem. Pharm. Bull., 42 (1994) 489.

    Google Scholar 

  13. Gurunath, R. and Balaram, P., Biopolymers, 35 (1995) 21.

    Google Scholar 

  14. Monaco, V., Formaggio, F., Crisma, M., Toniolo, C., Shui, X. and Eggleston, D.S., Biopolymers, 39 (1996) 31.

    Google Scholar 

  15. Karle, I.L. and Balaram, P., Biochemistry, 29 (1990) 6747.

    Google Scholar 

  16. Toniolo, C. and Benedetti, E., Macromolecules, 24 (1991) 4004.

    Google Scholar 

  17. McGahren, W.J. and Goodman, M., Tetrahedron, 23 (1967) 2017.

    Google Scholar 

  18. Valle, G., Formaggio, F., Crisma, M., Bonora, G.M., Toniolo, C., Bavoso, A., Benedetti, E., Di Blasio, B., Pavone, V. and Pedone, C., J. Chem. Soc., Perkin Trans. 2, (1986) 1371.

    Google Scholar 

  19. Piazza, C., Formaggio, F., Crisma, M., Toniolo, C., Kamphuis, J. and Broxterman, Q.B., J. Pept. Sci., 5 (1999) 96.

    Google Scholar 

  20. Formaggio, F., Crisma, M., Bonora, G.M., Pantano, M., Valle, G., Toniolo, C., Aubry, A., Bayeul, D. and Kamphuis, J., Pept. Res., 8 (1995) 6.

    Google Scholar 

  21. Carpino, L.A., J. Am. Chem. Soc., 115 (1993) 4397.

    Google Scholar 

  22. El-Hajji, M., Rebuffat, S., Doan, T.L., Klein, G., Satre, M. and Bodo, B., Biochim. Biophys. Acta, 978 (1989) 97.

    Google Scholar 

  23. Kruizinga, W.H., Bolster, J., Kellogg, R.M., Kamphuis, J., Boesten, W.H.J., Meijer, E.M. and Schoemaker, H.E., J. Org. Chem., 53 (1988) 1826.

    Google Scholar 

  24. Elferink, V.H.M., Breitgoff, D., Kloosterman, M., Kamphuis, J., Van den Tweel, W.J.J. and Meijer, E.M., Recl. Trav. Chim. Pays-Bas, 110 (1991) 63.

    Google Scholar 

  25. Kaptein, B., Boesten, W.H.J., Broxterman, Q.B., Peters, P.J.H., Schoemaker, H.E. and Kamphuis, J., Tetrahedron: Asymmetry, 4 (1993) 1113.

    Google Scholar 

  26. Brown, H.C. and Narasimhan, S., J. Org. Chem., 47 (1982) 1604.

    Google Scholar 

  27. Bonora, G.M., Mapelli, C., Toniolo, C., Wilkening, R.R. and Stevens, E.S., Int. J. Biol. Macromol., 6 (1984) 179.

    Google Scholar 

  28. Toniolo, C., Bonora, G.M., Barone, V., Bavoso, A., Benedetti, E., Di Blasio, B., Grimaldi, P., Lelj, F., Pavone, V. and Pedone, C., Macromolecules, 18 (1985) 895.

    Google Scholar 

  29. Kennedy, D.F., Crisma, M., Toniolo, C. and Chapman, D., Biochemistry, 30 (1991) 6541.

    Google Scholar 

  30. Beychok, S., In Fasman, G.D. (Ed.), Poly-α-Amino Acids: Protein Models for Conformational Studies, Marcel Dekker, New York, NY, 1967, pp. 293-337.

    Google Scholar 

  31. Toniolo, C., Polese, A., Formaggio, F., Crisma, M. and Kamphuis, J., J. Am. Chem. Soc., 118 (1996) 2744.

    Google Scholar 

  32. Wade, D., Boman, A., Wahlin, B., Drain, C.M., Andreu, D., Boman, H.G. and Merrifield, R.B., Proc. Natl. Acad. Sci. USA, 87 (1990) 4761.

    Google Scholar 

  33. Merrifield, R.B., Juvvadi, P., Andreu, D., Ubach, J., Boman, A. and Boman, H.G., Proc. Natl. Acad. Sci. USA, 92 (1995) 3449.

    Google Scholar 

  34. Hauge, H.H., Mantzilas, D., Moll, G.N., Konings, W.N., Driessen, A.J.M., Eijsink, V.G.H. and Nissen-Meyer, J., Biochemistry, 37 (1998) 16026.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Biopolymer Research Centre, C.N.R., Department of Organic Chemistry, University of Padova, via Marzolo 1, I-35131, Padova, Italy

    Cristina Peggion, Claudia Piazza, Fernando Formaggio, Marco Crisma & Claudio Toniolo

  2. Organic Chemistry and Biotechnology Section, DSM Research, P.O. Box 18, 6160 MD, Geleen, The Netherlands

    Bernard Kaptein & Quirinus B. Broxterman

  3. DSM Speciality Intermediates, P.O. Box 5489, 6130 PL, Sittard, The Netherlands

    Johan Kamphuis

Authors
  1. Cristina Peggion
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Claudia Piazza
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Fernando Formaggio
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Marco Crisma
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Claudio Toniolo
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Bernard Kaptein
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Quirinus B. Broxterman
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Johan Kamphuis
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Peggion, C., Piazza, C., Formaggio, F. et al. Synthesis, conformation, and membrane modifying properties of the trikoningin KB lipopeptaibols: Effect of hydrophobicity and chirality in position 1. Letters in Peptide Science 7, 9–16 (2000). https://doi.org/10.1023/A:1008934505586

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1008934505586

Search

Navigation