Skip to main content
Log in

Analogs of purine nucleosides and purine mono- and polynucleotides

III. Intermolecular and intramolecular interactions IN 6-Substitued 9-(α,Ω-dihydroxyalkyl)purines

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

On the basis of a comparison of the protolysis constants and vibrational frequencies it is shown that intermolecular interactions are present in 6-substituted 9-(α,Ω-dihydroxyalkyl)-purines and the corresponding mono- and diphosphates. In addition, in the case of the phosphates the existence of intramolecular interactions of electrostatic character between the phosphate group and the heteroring is also proposed. A comparison of the protolysis constants provides evidence for the different character of the interaction of the dihydroxyalkyl residue with the heteroring of the base in series of adenine and hypoxanthine derivatives.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

Literature cited

  1. S. A. Giller, I. N. Getsova, I. N. Goncharova, L. N. Petrulyanis, L. I. Mironova, G. F. Nazarova, and é. I. Bruk, Khim. Geterotsikl. Soedin., 1680 (1974).

  2. S. A. Giller, I. N. Goncharova, I. N. Getsova, L. I. Mironova, é. I. Bruk, G. F. Nazarova, and L. N. Petrulyanis, Khim. Geterotsikl. Soedin., 1674 (1974).

  3. Y. Clauwaert and Y. Z. Stockx, Naturforsch., 23b, 25 (1968).

    Google Scholar 

  4. A. Albert and D. J. Brown, J. Chem. Soc., 2060 (1954).

  5. R. Phillips, Chem. Rev., 66, 501 (1966).

    Google Scholar 

  6. C. L. Angell, J. Chem. Soc., 504 (1961).

  7. G. P. Zhizhina and é. F. Oleinik, Usp. Khim., 37, 474 (1972).

    Google Scholar 

  8. R. Bonaccorsi, A. Pullman, E. Scrocco, and J. Tomasi, Theor. Chim. Acta, 24, 51 (1972).

    Google Scholar 

  9. N. K. Kochetkov, é. I. Budovskii, E. D. Sverdlov, N. A. Simukova, M. F. Turchinskii, and V. I. Shibarev, The Organic Chemistry of Nucleic Acids [in Russian], Khimiya, Moscow (1970).

    Google Scholar 

  10. L. Bellamy, New Data on the IR Spectra of Complex Molecules [Russian translation], Mir, Moscow (1971).

    Google Scholar 

  11. R. F. Stewart and L. H. Jensen, J. Chem. Phys., 40, 2071 (1964).

    Google Scholar 

  12. R. Phillips, S. J. P. Eisenberg, and R. J. Putman, J. Biol. Chem., 240, 4393 (1965).

    Google Scholar 

  13. M. Sundaralingam, Acta Cryst., 21, 495 (1966).

    Google Scholar 

  14. Y. Kyogoku, M. Tsuboi, and T. Shimanouchi, Nature, 189, 120 (1961).

    Google Scholar 

  15. M. Yu. Lidak, I. V. Dipan, R. A. Paegle, and Ya. P. Stradyn', Khim. Geterotsikl. Soedin., 708 (1972).

  16. A. Albert and E. Serjeant, Ionization Constants of Acids and Bases, Methuen (1962).

Download references

Author information

Authors and Affiliations

Authors

Additional information

See [1] for communication II.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1684–1689, December, 1974.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Giller, S.A., Goncharova, I.N., Getsova, I.N. et al. Analogs of purine nucleosides and purine mono- and polynucleotides. Chem Heterocycl Compd 10, 1481–1485 (1974). https://doi.org/10.1007/BF00474335

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00474335

Keywords

Navigation