Skip to main content
SpringerLink
Log in

A study of the conformational states of cyclopeptide systems III. Cyclohexapeptides as systems of interacting amide chromophores

  • Published:
Chemistry of Natural Compounds Aims and scope

Summary

1. The UV spectra of aqueous solutions of cyclohexapeptides constructed of L(D)-alanine and glycine residues exhibit a considerable (about 45%) hypochromism of the band of the π→π* transition which has hitherto been observed among peptide-protein systems only in α-helical polypeptides.

2. In water, almost all the polypeptides studied have monotypical CD and ORD curves characterized by two Cotton effects of opposite sign in the region of the π→π* transition.

3. The features of the optical properties of the cyclohexapeptides are connected with the exciton interaction of the amide chromophores in the "pleated sheet" conformation. The neglect of such interactions may lead to high results in the determination of the degree of helicity in proteins from CD and ORD observations.

4. On passing to less polar solvents, there is a redistribution of the intensities of the Cotton effects connected with a conformational rearrangement of the cyclohexapeptides.

The authors express their gratitude to Professor E. Scoffone (Institute of Organic Chemistry, University of Padua, Italy) for kindly providing one of us (VTI) with the possibility of performing measurements on Cary-15 and JOUAN 11 instruments.

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

Literature cited

  1. Yu. A. Ovchinnikov, V. T. Ivanov, V. V. Shilin, and G. A. Kogan, Mol. Biol.,3, 600 (1969).

    CAS  Google Scholar 

  2. V. T. Ivanov, V. V. Shilin, Ya. Bernat, and Yu. A. Ovchinnikov, Zh. Obshch. Khim.,41, 2318 (1971).

    CAS  Google Scholar 

  3. S. L. Portnova, T. A. Balashova, V. F. Bystrov, V. V. Shilin, Ya. Bernat, V. T. Ivanov, and Yu. A. Ovchinnikov, Khim. Prirodn. Soedin.,7, 323 (1971).

    CAS  Google Scholar 

  4. V. T. Ivanov, S. L. Portnova, T. A. Balashova, V. F. Bystrov, V. V. Shilin, Yu. A. Ovchinnikov, and Ya. Bernat, Khim. Prirodn. Soedin.,7, 339 (1971).

    CAS  Google Scholar 

  5. V. T. Ivanov, L. B. Senyavina, E. S. Efremov, V. V. Shilin, and Yu. A. Ovchinnikov, Khim. Prirodn. Soedin.,7, 347 (1971).

    CAS  Google Scholar 

  6. M. Avignon, P. V. Huong, J. Lascombe, M. Marrand, and J. Neel, Biopolymers,8, 69 (1969).

    Article  CAS  Google Scholar 

  7. H. Basch, M. B. Robin, and N. A. Kuebler, J. Chem. Phys.,47, 1201 (1967).

    Article  CAS  Google Scholar 

  8. D. G. Barnes and W. Rhodes, J. Chem. Phys.,48, 817 (1968).

    Article  CAS  Google Scholar 

  9. H. Basch, M. B. Robin, and N. A. Kuebler, J. Chem. Phys.,49, 5007 (1968).

    Article  CAS  Google Scholar 

  10. W. B. Gratzer, W. Rhodes, and G. D. Fasman, Biopolymers,1, 319 (1963).

    Article  CAS  Google Scholar 

  11. W. B. Gratzer, Poly-α-Amino Acids. Protein Models for Conformational Studies, Marcel Dekker, Inc., New York (1967), p. 182.

    Google Scholar 

  12. K. Rosenheck and P. Doty, Proc. Nat. Acad. Sci. U. S.,47, 1775 (1961).

    Article  CAS  Google Scholar 

  13. E. B. Nielsen and J. A. Schellman, J. Phys. Chem.,71, 2297 (1967).

    Article  CAS  Google Scholar 

  14. M. D'Alagni, B. Pipsia, and F. Quadrifoglio, La Ricerca Scientifica,38, 910 (1968).

    CAS  Google Scholar 

  15. I. Tinoco, J. Amer. Chem. Soc.,82, 4785 (1960).

    Article  CAS  Google Scholar 

  16. W. Rhodes, J. Amer. Chem. Soc.,83, 3609 (1961).

    Article  CAS  Google Scholar 

  17. H. De Voe, Biopolymer Symposia, No. 1, 251 (1964).

  18. A. McLachlan and M. Ball., Mol. Phys.,8, 581 (1964).

    Article  CAS  Google Scholar 

  19. G. Holzwarth and P. Doty, J. Amer. Chem. Soc.,87, 218 (1965).

    Article  CAS  Google Scholar 

  20. K. Rosenheck and B. Sommer, J. Chem. Phys.,46, 532 (1967).

    Article  CAS  Google Scholar 

  21. I. Karle and J. Karle, Acta Cryst.,16, 969 (1963).

    Article  CAS  Google Scholar 

  22. D. W. Urry, J. Phys. Chem.,72, 3035 (1968).

    Article  CAS  Google Scholar 

  23. D. W. Urry, A. L. Ruiter, B. C. Starcher, and T. A. Hinners, Antimicrobial Agents and Chemotherapy (1968), p. 87.

  24. S. Laiken, M. Printz, and L. C. Craig, J. Biol. Chem.,244, 4454 (1969).

    CAS  PubMed  Google Scholar 

  25. F. Quadrifoglio and D. W. Urry, J. Amer. Chem. Soc.,90, 2755 (1968).

    Article  CAS  Google Scholar 

  26. F. Quadrifoglio and D. W. Urry, J. Amer. Chem. Soc.,90, 2760 (1968).

    Article  CAS  Google Scholar 

  27. J. E. Shields and S. T. McDowell, J. Amer. Chem. Soc.,89, 2499 (1967).

    Article  CAS  Google Scholar 

  28. D. Balasubramanian, J. Amer. Chem. Soc.,89, 5445 (1967).

    Article  CAS  Google Scholar 

  29. M. A. Ruttenberg, T. P. King, and L. C. Craig, J. Amer. Chem. Soc.,87, 4196 (1965).

    Article  CAS  Google Scholar 

  30. F. Quadrifoglio and D. W. Urry, Biochem. Biophys. Res. Commun.,29, 785 (1967).

    Article  CAS  Google Scholar 

  31. L. C. Craig, Proc. Nat. Acad. Sci. U. S.,61, 152 (1968).

    Article  CAS  Google Scholar 

  32. Yu. A. Ovchinnikov, V. T. Ivanov, V. F. Bystrov, A. I. Miroshnikov, E. N. Shepel, N. D. Abdullaev, E. S. Efremov, and L. B. Senyavina, Biochem. Biophys. Res. Commun.,39, 217 (1970).

    Article  CAS  Google Scholar 

  33. K. A. Zykalova, G. N. Tishchenko, G. A. Kogan, and V. T. Ivanov, Izv. Akad. Nauk SSSR, Ser. Khim.,1970, 1547.

  34. M. Legrand and R. Viennet, Compt. Rend.,C262, 943 (1966).

    CAS  Google Scholar 

  35. F. A. Quiocho, W. H. Bishop, and F. M. Richards, Symposium on Three-dimensional Structure of Macromolecules of Biological Origin, Proc. Nat. Acad. Sci., U. S.,57, 525 (1967).

    Article  CAS  Google Scholar 

  36. B. W. Mattews, P. B. Sigler, R. Henderson, and D. M. Blow, Nature,241, 652 (1967).

    Article  Google Scholar 

  37. N. Greenfield and G. D. Fasman, J. Biochem.,8, 4108 (1969).

    Article  CAS  Google Scholar 

  38. G. M. Grippen and H. A. Scheraga, Proc. Nat. Acad. Sci. U. S.,64, 42 (1969).

    Article  Google Scholar 

  39. D. W. Urry and P. J. Doty, J. Amer. Chem. Soc.,87, 2756 (1965).

    Article  CAS  Google Scholar 

  40. D. D. Ulmer, J. Biochem.,4, 902 (1965).

    Article  CAS  Google Scholar 

  41. D. E. Dickerson, M. L. Kopka, J. E. Weinzierl, J. C. Varnum, D. Eisenberg, and E. Margoliash, Abstr. 15th Natl. Meeting, Am. Chem. Soc., Chicago, Sept. (1967).

  42. K. Blàha and I. Fric, Peptides, North-Holland Publ. Comp., Amsterdam (1968), p. 40.

    Google Scholar 

  43. K. Blàha, I. Fric, and J. Rudinger, Collection Czech. Chem. Commun.,34, 3497 (1969).

    Article  Google Scholar 

  44. D. L. Coleman and E. R. Blout, Conformation of Biopolymers, Vol. 1, Academic Press, New York (1967), p. 123.

    Google Scholar 

  45. M. M. Shemyakin, Yu. A. Ovchinnikov, V. T. Ivanov, V. K. Antonov, E. I. Vinogradova, A. M. Shkrob, G. G. Malenkov, A. V. Evstratov, I. A. Laine, E. I. Melnik, and I. D. Ryabova, J. Membrane Biol.,1, 402 (1969).

    Article  CAS  Google Scholar 

Download references

Authors
  1. V. T. Ivanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. A. Kogan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. A. Meshcheryakova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. V. Shilin
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yu. A. Ovchinnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

M. M. Shemyakin Institute of the Chemistry of Natural Compounds of the Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 309–323, May–June, 1971.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ivanov, V.T., Kogan, G.A., Meshcheryakova, E.A. et al. A study of the conformational states of cyclopeptide systems III. Cyclohexapeptides as systems of interacting amide chromophores. Chem Nat Compd 7, 297–306 (1971). https://doi.org/10.1007/BF00569004

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00569004

Keywords

Search

Navigation