Chemistry of Natural Compounds

, Volume 22, Issue 2, pp 213–218 | Cite as

Comparative characteristics of methods for obtaining oligodeoxyribonucleotide 3′-phosphates

  • E. M. Volkov
  • S. M. Gryaznov
  • N. F. Krynetskaya
  • T. S. Oretskaya
  • V. K. Potapov
Article
  • 17 Downloads

Abstract

Methods of obtaining oligodeoxyribonucleotide 3′-phosphates based on the triester synthesis of oligodeoxyribonucleotides are discussed. These methods can be divided into two classes: I) phosphorylation of the 3′-OH group in a protected oligo-deoxyribonucleotide; and II) modification of a terminal nucleotide 3′-phosphate. It has been shown that a universal method is the preparation of an oligonucleotide with a 3′-terminal uridine residue followed by its oxidative elimination. The methods discussed in the paper have been used for obtaining a set of oligodeoxyribonucleotide 3′-phosphates required for the chemical “cross-linking” of oligonucleotides in DNA duplexes.

Keywords

Phosphate Nucleotide Organic Chemistry Uridine Comparative Characteristic 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    A. A. Purnal', V. L. Drutsa, and Z. A. Shabarova, Bioorg. Khim.,10, 394 (1984).Google Scholar
  2. 2.
    Z. A. Shabarova, N. G. Dolinnaya, V. L. Drutsa, N. P. Melnikova, and A. A. Purmal, Nucleic Acids Res.,9, 5747 (1981).Google Scholar
  3. 3.
    V. P. Veiko, T. S. Oretskaya, E. M. Volkov, V. G. Metelev, E. A. Romanova, and V. K. Potapov, Khim. Prir. Soedin., 637 (1984).Google Scholar
  4. 4.
    J. H. Van Boom and P. H. J. Burgers, Tetrahedron Lett.,52, 4875 (1976).Google Scholar
  5. 5.
    N. F. Sergeeva, V. D. Smirnov, Z. A. Shabarova, M. A. Prokof'ev, V. F. Zarytova, A. V. Lebedev, and D. G. Knorre, Bioorg. Khim.,2, 1056 (1976).Google Scholar
  6. 6.
    Z. A. Shabarova, E. M. Volkov, T. S. Oretskaya, S. I. Turkin, N. G. Dolinnaya, V. K. Kagramanova, and M. A. Prokof'ev, Dokl. Akad. Nauk SSSR,258, 914 (1981).Google Scholar
  7. 7.
    A. M. Maxam and W. Gilbert, Methods Enzymol.,65, 499 (1980).Google Scholar
  8. 8.
    G. R. Gough, M. I. Brunden, and P. T. Gilham, Tetrahedron Lett.,24, 5317 (1983).Google Scholar
  9. 9.
    D. M. Brown, M. Fried, and A. R. Todd, J. Chem. Soc., 2206 (1953).Google Scholar
  10. 10.
    H. D. New and L. A. Heppel, J. Biol. Chem.,239, 2927 (1964).Google Scholar
  11. 11.
    J. G. Nadeau, C. H. Singleton, G. B. Kelly, H. L. Werth, and G. R. Gough, Biochemistry,23, 6153 (1984).Google Scholar
  12. 12.
    G. S. Ti, B. L. Gaffney, and R. A. Jones, J. Am. Chem. Soc.,104, 1316 (1982).Google Scholar

Copyright information

© Plenum Publishing Corporation 1986

Authors and Affiliations

  • E. M. Volkov
  • S. M. Gryaznov
  • N. F. Krynetskaya
  • T. S. Oretskaya
  • V. K. Potapov

There are no affiliations available

Personalised recommendations