Skip to main content
SpringerLink
Log in

Afc can adopt either the fully extended or a turn conformation

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

Abstract

We have synthesized by solution methods and fully characterizedtwo sets of terminally protected peptides based on the tricyclic Cα α-disubstituted glycine Afc. Theconformational preferences of the Afc/Gly peptides were examined by FT-IR absorption and 1H NMR techniques, whilethose of the Afc/TOAC peptides were primarily investigated by using fluorescence spectroscopy. The X-ray diffraction structure of an Afc derivative was also analyzed. The body of solution and crystal-state experimental data conclusively confirms previous findings that the Afc residue may either adopt the fully extended (C5) or a turn conformation.

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. Naydenova, E.D., Popova, J.S. and Aleksiev, B.V., In Ramage, R. and Epton, R. (Eds.), Peptides 1996, Mayflower Scientific, Kingswinford, U.K., 1998, pp. 675–676.

    Google Scholar 

  2. Savrda, J., Mazaleyrat, J.-P., Wakselman, M., Formaggio, F., Crisma, M. and Toniolo, C., J. Pept. Sci., 5 (1999) 61.

    Google Scholar 

  3. Toniolo, C., Crisma, M., Formaggio, F., Savrda, J., Mazaleyrat, J.-P. and Wakselman, M., In Bajusz, S. and Hudecz, F. (Eds.), Peptides 1998, Akadémiai Kiadó, Budapest, 1999, pp. 390–391.

    Google Scholar 

  4. DuPriest, M.T., Conrow, R.E. and Kuzmich, D., Tetrahedron Lett., 31 (1990) 2959.

    Google Scholar 

  5. Toniolo, C., CRC Crit. Rev. Biochem., 9 (1980) 1.

    Google Scholar 

  6. Yamada, T., Makihira, K., Suzuki, S., Yoneda, K., Yanagihara, R. and Miyazawa, T., In Shimonishi, Y. (Ed.), Peptide Science: Present and Future, Kluwer, Dordrecht, The Netherlands, 1999, pp. 300–302.

    Google Scholar 

  7. Yamada, T., Makihira, K., Suzuki, S., Yanagihara, R. and Miyazawa, T., In Bajusz, S. and Hudecz, F. (Eds.), Peptides 1998, Akadémiai Kiadó, Budapest, 1999, pp. 404–405.

    Google Scholar 

  8. Marshall, G.R., In Kharasch, N. (Ed.), Intra-Science Chemistry Reports, Gordon and Breach, New York, NY, 1971, pp. 305–316.

    Google Scholar 

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

    Google Scholar 

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

    Google Scholar 

  11. Toniolo, C., Crisma, M., Fabiano, N., Melchiorri, P., Negri, L., Krause, J.A. and Eggleston, D.S., Int. J. Pept. Protein Res., 44 (1994) 85.

    Google Scholar 

  12. Pavone, V., Lombardi, A., Saviano, M., Nastri, F., Zaccaro, L., Maglio, O., Pedone, C., Omote, Y., Yamanaka, Y. and Yamada, T., J. Pept. Sci., 4 (1998) 21.

    Google Scholar 

  13. Toniolo, C., Crisma, M. and Formaggio, F., Biopolymers (Pept. Sci.), 47 (1998) 153.

    Google Scholar 

  14. Pispisa, B., Palleschi, A., Stella, L., Venanzi, M. and Toniolo, C., J. Phys. Chem., B 102 (1998) 7890.

    Google Scholar 

  15. Sheldrick, G.M., SHELXS 86. Program for the Solution of Crystal Structures, University of Göttingen, Göttingen, Germany, 1986.

    Google Scholar 

  16. Sheldrick, G.M., SHELXL 93. Program for Crystal Structure Refinement, University of Göttingen, Göttingen, Germany, 1993.

    Google Scholar 

  17. Belleau, B. and Malek, G., J. Am. Chem. Soc., 90 (1968) 1651.

    Google Scholar 

  18. Nakaje, C.R., Schreier, S. and Paiva, A.C.M., Biochim. Biophys. Acta, 742 (1983) 63.

    Google Scholar 

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

    Google Scholar 

  20. Chakrabarti, P. and Dunitz, J.D., Helv. Chim. Acta, 65 (1982) 1555.

    Google Scholar 

  21. Schweizer, W.B. and Dunitz, J.D., Helv. Chim. Acta, 65 (1982) 1547.

    Google Scholar 

  22. Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G. and Taylor, R., J. Chem. Soc., Perkin Trans. 2, (1987) S1.

  23. Valle, G., Crisma, M. and Toniolo, C., Can. J. Chem., 66 (1988) 2575.

    Google Scholar 

  24. IUPAC-IUB Commission on Biochemical Nomenclature, Biochemistry, 9 (1970) 3471.

    Google Scholar 

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

    Google Scholar 

  26. Crisma, M., Formaggio, F., Toniolo, C., Yoshikawa, T. and Wakamiya, T., J. Am. Chem. Soc., 121 (1999) 3272.

    Google Scholar 

  27. Crisma, M., Bonora, G.M., Toniolo, C., Benedetti, E., Bavoso, A., Di Blasio, B., Pavone, V. and Pedone, C., Int. J. Biol. Macromol., 10 (1988) 300.

    Google Scholar 

  28. Kopple, K.D. and Ohnishi, M., Biochemistry, 8 (1969) 4087.

    Google Scholar 

  29. Martin, D. and Hauthal, H.G. (Eds.), Dimethyl Sulphoxide, Van Nostrand-Rheinhold, Wokingham, U.K., 1975.

    Google Scholar 

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

    Google Scholar 

  31. Venkatachalam, C.M., Biopolymers, 6 (1968) 1425.

    Google Scholar 

  32. Rose, G.D., Gierasch, L.M. and Smith, J.P., Adv. Protein Chem., 37 (1985) 1.

    Google Scholar 

  33. Toniolo, C. and Benedetti, E., Trends Biochem. Sci., 16 (1991) 350.

    Google Scholar 

  34. Mezzato, S., Chemistry Degree Thesis, Department of Organic Chemistry, University of Padova, Italy, 1999.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Biopolymer Research Center, CNR, Department of Organic Chemistry, University of Padova, Marzolo 1, I-35131, Padova, Italy

    Marco Crisma, Fernando Formaggio & Stefano Mezzato

  2. Biopolymer Research Center, CNR, Department of Organic Chemistry, University of Padova, Marzolo 1, I-35131, Padova, Italy

    Claudio Toniolo

  3. SIRCOB, Bât. Lavoisier, University ofVersailles, F-78000, Versailles, France

    Jaroslav Savrda, Jean-Paul Mazaleyrat & Michel Wakselman

Authors
  1. Marco Crisma
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Fernando Formaggio
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Stefano Mezzato
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Claudio Toniolo
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Jaroslav Savrda
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Jean-Paul Mazaleyrat
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Michel Wakselman
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Claudio Toniolo.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Crisma, M., Formaggio, F., Mezzato, S. et al. Afc can adopt either the fully extended or a turn conformation. Letters in Peptide Science 7, 123–131 (2000). https://doi.org/10.1023/A:1008915732443

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1008915732443

Search

Navigation