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Phosphoramidite reagents and solid-phase supports based on hydroxyprolinol for the synthesis of modified oligonucleotides

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Abstract

The synthesis of phosphoramidite reagents and solid-phase supports based on hydroxyprolinol for the introduction of the residues of biotin, lipoic acid, amino groups, and terminal acetylene groups at different positions of the oligonucleotide chain has been described. The efficiency of the reagents and supports has been confirmed by the synthesis of the corresponding modified oligonucleotides.

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Abbreviations

CPG:

controlled pore glass

DIPС:

diisopropylcarbodiimide

DIPEA:

diisopropylethylamine

DMAP:

4-dimethylaminopyridine

DMTr:

dimethoxytrityl

PyBOP:

benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate

minR:

minor rotamer

majR:

major rotamer

dst:

diastereomer

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Authors and Affiliations

  1. Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, Minsk, 220072, Belarus

    M. Yu. Tatulchenkov, M. V. Kvach, N. V. Pilchenko, O. L. Sharko & V. V. Shmanai

  2. Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, 117997, Russia

    I. A. Prokhorenko, I. A. Stepanova & V. A. Korshun

  3. Gauze Institute of New Antibiotics, Moscow, 119021, Russia

    I. A. Prokhorenko & V. A. Korshun

  4. ALC Primetech, Minsk, 220072, Belarus

    M. E. Navakouski, N. V. Pilchenko & S. V. Gontarev

Authors
  1. M. Yu. Tatulchenkov
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  2. I. A. Prokhorenko
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  3. M. V. Kvach
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  4. M. E. Navakouski
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  5. I. A. Stepanova
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  6. N. V. Pilchenko
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  7. S. V. Gontarev
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  8. O. L. Sharko
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  9. V. A. Korshun
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  10. V. V. Shmanai
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Corresponding author

Correspondence to V. V. Shmanai.

Additional information

Original Russian Text © M.Yu. Tatulchenkov, I.A. Prokhorenko, M.V. Kvach, M.E. Navakouski, I.A. Stepanova, N.V. Pilchenko, S.V. Gontarev, O.L. Sharko, V.A. Korshun, V.V. Shmanai, 2017, published in Bioorganicheskaya Khimiya, 2017, Vol. 43, No. 4, pp. 377–387.

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Tatulchenkov, M.Y., Prokhorenko, I.A., Kvach, M.V. et al. Phosphoramidite reagents and solid-phase supports based on hydroxyprolinol for the synthesis of modified oligonucleotides. Russ J Bioorg Chem 43, 386–396 (2017). https://doi.org/10.1134/S1068162017040148

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  • DOI: https://doi.org/10.1134/S1068162017040148

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