Abstract
Two methods for synthesizing oligodeoxyribonucleotides containing 3'-terminal phosphosphate groups have been developed. The first consists in the synthesis and the introduction into the oligonucleotides of a block containing a 3'-terminal bis(2-cyanoethyl) phosphate group and the second in the use of the transesterification reaction of oligonucleotides with 2-cyanoethanol in the presence of cesium fluoride. Both methods permit the fairly effective synthesis of oligodeoxyribonucleotide 3'-phosphates.
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Literature cited
R. Naylor and P. T. Gilham, Biochemistry,5, 2722 (1966).
Z. A. Shabarova, N. G. Dolinnaya, V. L. Drutsa, N. P. Melnikova, and A. A. Purmal, Nucleic Acids Res.,9, 5747 (1981).
A. G. Badashkeeva, G. N. Kabasheva, D. G. Knorre, G. G. Shamovskii, and T. N. Shubina, Dokl. Akad. Nauk SSSR,206, 870 (1972).
J. Stawinski, T. Hozumi, S. A. Narang, C. P. Bahl, and R. Wu, Nucleic Acid Res.,4, 353 (1977).
Z. A. Shabarova, E. M. Volkov, T. S. Oretskaya, S. I. Turkin, N. G. Dolinnaya, V. K. Karpamanova, and M. A. Prokof'ev, Dokl. Akad. Nauk SSSR,258, 914 (1981).
V. K. Potapov, V. P. Veiko, E. M. Volkov, T. S. Oretskaya, T. R. Telesnina, Z. A. Shabarova, and M. A. Prokof'ev, Dokl. Akad. Nauk SSSR,260, 40 (1981).
G. M. Tener, J. Am. Chem. Soc.,83, 159 (1961).
V. A. Efimov, S. V. Reverdatto, and O. G. Chakhmakhcheva, Tetrahedron Lett.,23, 961 (1982).
J. H. Van Boom and P. H. J. Burgers, Tetrahedron Lett.,52, 4875 (1976).
A. H. Maxam and W. Gilbert, Methods Enzymol.,65, 499 (1980).
V. A. Petrenko, P. I. Pozdnyakov, G. F. Sivolobova, and T. N. Shubina, Bioorg. Khim.,6, 431 (1980).
G. S. Ti, B. L. Gaffney, and R. A. Jones, J. Am. Chem. Soc.,104, 1316 (1982).
R. Crea, A. Kraszewski, T. Hirose, and K. Itakura, Proc. Natl. Acad. Sci. USA,75, 5765 (1978).
Additional information
M. V. Lomonosov Moscow State University. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 637–641, September–October, 1984.
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Veiko, V.P., Oretskaya, T.S., Volkov, E.M. et al. Synthesis of oligodeoxyribonucleotides containing a 3'-terminal phosphate group. Chem Nat Compd 20, 601–605 (1984). https://doi.org/10.1007/BF00580075
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DOI: https://doi.org/10.1007/BF00580075