Synthesis and Properties of Modified Oligodeoxyribonucleotides Containing 9-(2-Amino-2-deoxy-β-D-arabinofuranosyl)adenine

Eugene M. Zubin Chemical Department, A.N. Belozersky Institute of Physical Chemical Biology M. V. Lomonosov Moscow State University, Moscow, 119899, Russia

Sergey I. Antsypovich Chemical Department, A.N. Belozersky Institute of Physical Chemical Biology M. V. Lomonosov Moscow State University, Moscow, 119899, Russia

Tatiana S. Oretskaya Chemical Department, A.N. Belozersky Institute of Physical Chemical Biology M. V. Lomonosov Moscow State University, Moscow, 119899, Russia

Elena A. Romanova Chemical Department, A.N. Belozersky Institute of Physical Chemical Biology M. V. Lomonosov Moscow State University, Moscow, 119899, Russia

Eugene M. Volkov Chemical Department, A.N. Belozersky Institute of Physical Chemical Biology M. V. Lomonosov Moscow State University, Moscow, 119899, Russia

Vadim N. Tashlitsky Chemical Department, A.N. Belozersky Institute of Physical Chemical Biology M. V. Lomonosov Moscow State University, Moscow, 119899, Russia

Nina G. Dolinnaya Chemical Department, A.N. Belozersky Institute of Physical Chemical Biology M. V. Lomonosov Moscow State University, Moscow, 119899, Russia

Zoe A. Shabarova Chemical Department, A.N. Belozersky Institute of Physical Chemical Biology M. V. Lomonosov Moscow State University, Moscow, 119899, Russia

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Abstract

The synthesis of modified oligodeoxyribonucleotidesFootnote# containing 2′-amino-2′-deoxyarabinoadenosine residues (aAⁿ) was carried out by means of the standard phosphoramidite chemistry. A high reactivity of such compounds to electrophilic reagents was shown. The cross-link formation between 2′-amino group of aAⁿ and carboxyl function introduced into complementary strands occurs with 55% yield. The aAⁿ residues was shown to induce the increased resistance of modified oligomers towards the enzymatic cleavage and provide the insignificant destabilization of DNA duplexes.

This publication is dedicated to Professor Tsujiaki Hata, who made a valuable contribution to the chemistry of nucleosides and nucleotides.

Notes

This publication is dedicated to Professor Tsujiaki Hata, who made a valuable contribution to the chemistry of nucleosides and nucleotides.

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Synthesis and Properties of Modified Oligodeoxyribonucleotides Containing 9-(2-Amino-2-deoxy-β-D-arabinofuranosyl)adenine

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Synthesis and Properties of Modified Oligodeoxyribonucleotides Containing 9-(2-Amino-2-deoxy-β-D-arabinofuranosyl)adenine

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