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Chemistry of Natural Compounds

, Volume 17, Issue 3, pp 281–284 | Cite as

Conformational properties of the 2′- and 3′-hydroxy groups of 5′-O-trityluridine

  • É. L. Kupche
Article
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Abstract

The results of a study of the temperature dependence of the SSCCs of the hydroxyl protons in the PMR spectra of 5′-O-trityluridine indicate the existence of an intramolecular bond between the 2-keto oxygen of the base and the 2′-hydroxyl in deuterochloroform. Under these conditions, stabilization of the 3′-endo (N) conformation of the ribose ring is observed. The existence of the influence of the temperature on the population of the 3′-hydroxyl rotamers shows the formation of a hydrogen bond between OH-3′ and O-2′. In polar solvents free rotation of the hydroxy groups is observed.

Keywords

Apply Biochemistry Hydroxy Group Intramolecular Hydrogen Bond Conformational Property Pyrimidine Derivative 

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Literature cited

  1. 1.
    D. E. Davies and S. S. Danyluk, Can. J. Chem.,48, 3112 (1970).CrossRefGoogle Scholar
  2. 2.
    R. Deslauriers and I. C. P. Smith, Can. J. Chem.,51, 833 (1973).CrossRefGoogle Scholar
  3. 3.
    D. B. Davies and A. Rabozenko, J. Chem. Soc., Perkin Trans.,2, No. 15, 1703 (1975).CrossRefGoogle Scholar
  4. 4.
    N. K. Kochetkov, É. I. Budovskii, E. D. Sverdlov, M. F. Simukova, N. F. Turginskii, and V. N. Shibaev, The Organic Chemistry of the Nucleic Acids [in Russian], Moscow (1970), p. 141.Google Scholar
  5. 5.
    N. F. Myasoedov, C. V. Sidorov, and A. F. Usatyi, Khim. Prir. Soedin., 204 (1979).Google Scholar
  6. 6.
    M. P. Schweizer, A. D. Broom, P. O. P. Ts'o, and D. P. Hollis, J. Am. Chem. Soc.,90, 1042 (1968).CrossRefPubMedGoogle Scholar
  7. 7.
    P. R. Fraser, M. Kaufman, P. Morand, and G. Covil, Can. J. Chem.,47, 403 (1969).CrossRefGoogle Scholar
  8. 8.
    C. Altona and M. Sundaralingam, J. Am. Chem. Soc.,95, 2333 (1973).CrossRefPubMedPubMedCentralGoogle Scholar
  9. 9.
    K. N. Fang, N. S. Kondo, P. S. Miller, and P. O. P. T'so, J. Am. Chem. Soc.,93, 6647 (1971).CrossRefPubMedPubMedCentralGoogle Scholar

Copyright information

© Plenum Publishing Corporation 1982

Authors and Affiliations

  • É. L. Kupche

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