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Analogs of pyrimidine mono- and polynucleotides

VI. Phosphates of 1-(1, 4-dihydroxy-2-pentyl) thymine and 1-(1, 3-dihydroxy-2-propyl)uracil

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The corresponding monophosphates, cyclophosphates, and α, ω-diphosphates were obtained by phosphorylation of 1-(1, 4-dihydroxy-2-pentyl) thymine, 1-(1, 3-dihydroxy-2-propyl) uracil, and their derivatives with selective protection of one of the hydroxyl groups. 2-Cyanoethyl phosphate (CEP) in the presence of N, N′-dicyclohexylcarbodiimide (DCC), polyphosphoric acid, and pyrophosphoryl chloride were used as phosphorylating agents. The dependence of the yields of the products of phosphorylation of 1-(1, 4-dihydroxy-2-pentyl) thymine with CEP on the ratio of the reacting substances and the reaction time was studied. The monophosphates were cyclized under the influence of DCC. In the case of 1-(1, 3-dihydroxy-2-propyl) uracil 1-phosphate a dimeric phosphate was obtained in addition to a cyclophosphate. The acid hydrolysis of the cyclophosphates was investigated.

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Literature cited

  1. S. A. Giller, Z. A. Shomshtein, and T. A. Popova, Khim. Geterotsikl. Soedin., No. 4, 540 (1975).

    Google Scholar 

  2. S. A. Hiller, R. A. Zhuk, L. A. Sherinya, and D. E. Zarin, Nucleic Acids Res., Special Publication No. 1, 169 (1975).

  3. S. A. Giller, L. A. Sherin', R. A. Zhuk, and A. E. Berzinya, Khim. Geterotsikl. Soedin., No. 12, 1671 (1974).

    Google Scholar 

  4. S. A. Giller, T. A. Popova, and Z. A. Shomshtein, Khim. Geterotsikl. Soedin., No. 3, 401 (1975).

    Google Scholar 

  5. S. A. Giller, E. Ya. Gren, Z. A. Shomshtein, R. A. Zhuk, V. M. Berzin', P. P. Pumpen, and G. F. Rozental', Dokl. Akad. Nauk SSSR,221, 473 (1975).

    Google Scholar 

  6. R. A. Zhuk, L. A. Sherin', É. É. Liepin'sh, and S. A. Giller, Khim. Geterotsikl. Soedin., No. 12, 1666 (1974).

    Google Scholar 

  7. S. A. Hiller, D. E. Zarin, and R. A. Zhuk, Nucleic Acids Res.,3, 721 (1976).

    Google Scholar 

  8. A. M. Kritsyn, L. I. Kolobushkina, S. N. Mikhailov, and V. L. Florent'ev, Khim. Geterotsikl. Soedin., No. 1, 125 (1975).

    Google Scholar 

  9. K. Imai, S. Fujii, K. Takanohasi, Y. Furukawa, T. Masuda, and M. Hanjo, J. Org. Chem.,34, 1547 (1969).

    Google Scholar 

  10. N. G. Shinskii, N. N. Preobrazhenskaya, M. G. Ivanovskaya, Z. A. Shabarova, and M. A. Prokof'ev, Dokl. Akad. Nauk SSSR,184, 622 (1969).

    Google Scholar 

  11. H. G. Khorana, G. M. Tener, R. S. Wright, and J. G. Moffatt, J. Am. Chem. Soc.,79, 430 (1957).

    Google Scholar 

  12. M. M. Crutchfield, C. H. Dungan, J. H. Letcher, V. Mark, and J. R. Van Wazer, P31 Nuclear Magnetic Resonance Topics in Phosphorus Chemistry, Vol. 5, Wiley and Sons, New York (1967), p. 340.

    Google Scholar 

  13. G. M. Tener, J. Am. Chem. Soc.,83, 159 (1961).

    Google Scholar 

  14. H. Grunze, Monatsh. DAW DDR,5, 636 (1963).

    Google Scholar 

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See [1] for communication V; see [2] for a preliminary communication.

Deceased.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 678–683, May, 1978.

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Giller, S.A., Sherin', L.A., Zarin', D.É. et al. Analogs of pyrimidine mono- and polynucleotides. Chem Heterocycl Compd 14, 556–561 (1978). https://doi.org/10.1007/BF00673344

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  • DOI: https://doi.org/10.1007/BF00673344

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