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Functionalization of the Oligonucleotides Containing an Internucleotide Phosphoramidate Bond

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Abstract

A new method for functionalization of oligonucleotides by addition of aminoalkyl derivatives to the intermolecular phosphorus atom of the oligonucleotide N3"–P5" phosphoramidate bond in the presence of triphenylphosphine, 4-dimethylaminopyridine, and 2,2"-dipyridyl disulfide was suggested. The reaction proceeded with both low-molecular alkylamines (1,6-diaminohexane or N,N-dimethyl-1,3-diaminopropane) and a minor groove binder containing an aminoalkyl group.

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Authors and Affiliations

  1. Vector State Research Center of Virology and Biotechnology, Institute of Molecular Biology, pos. Kol'tsovo, Novosibirsk oblast, 630559, Russia

    A. N. Sinyakov & V. A. Ryabinin

  2. INSERM U565–CNRS UMR 8646, Muséum National d'Histoire Naturelle, Laboratoire de Biophysique, 43 rue Cuvier, 75231, Paris Cedex 05, France

    A. S. Boutorine & L. Halby

  3. Novosibirsk Institute of Bioorganic Chemistry, Siberian Division, Russian Academy of Sciences, pr. Akademika Lavrent'eva 8, Novosibirsk, 630090, Russia

    D. S. Novopashina

Authors
  1. A. N. Sinyakov
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  2. A. S. Boutorine
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  3. D. S. Novopashina
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  4. L. Halby
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  5. V. A. Ryabinin
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Correspondence to V. A. Ryabinin.

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Sinyakov, A.N., Boutorine, A.S., Novopashina, D.S. et al. Functionalization of the Oligonucleotides Containing an Internucleotide Phosphoramidate Bond. Russian Journal of Bioorganic Chemistry 29, 88–90 (2003). https://doi.org/10.1023/A:1022242822132

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  • DOI: https://doi.org/10.1023/A:1022242822132

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