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Monomers containing 2′-O-alkoxymethyl groups as synthons for the oligonucleotide synthesis by the phosphotriester method

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Abstract

A general scheme for the synthesis of ribonucleotides containing an alkoxymethyl group at the 2′-O-position of ribose and an O-nucleophilic catalytic 4-methoxy-1-oxido-2-picolyl phosphate-protecting group has been developed for the introduction into oligonucleotides during their solid-phase synthesis by the phosphotriester method. The scheme has been tested in the synthesis of monomers with 2′-O-modifying groups as examples: 2-azidoethoxymethyl, propargyloxymethyl, and 3,4-cyclocarbonatebutoxymethyl groups.

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Abbreviations

DBU:

diazabicyclo[5.4.0]undec-7-ene

DMTr:

4,4′-dimethoxytrityl

NIS:

N-iodosuccinimide

TEA:

triethyl-amine

TBAF:

tetra-n-butylammonium fluoride

TfOH:

trifluo-romethanesulfoacid

TPS:

2,4,6-triisopropylbenzenesulfonyl chloride

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Authors and Affiliations

  1. Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, ul. Miklukho-Maklaya 16/10, Moscow, 117997, Russia

    A. V. Aralov, V. N. Klykov, O. G. Chakhmakhcheva & V. A. Efimov

Authors
  1. A. V. Aralov
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  2. V. N. Klykov
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  3. O. G. Chakhmakhcheva
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  4. V. A. Efimov
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Correspondence to O. G. Chakhmakhcheva.

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Original Russian Text © A.V. Aralov, V.N. Klykov, O.G. Chakhmakhcheva, V.A. Efimov, 2011, published in Bioorganicheskaya Khimiya, 2011, Vol. 37, No. 5, pp. 654–661.

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Aralov, A.V., Klykov, V.N., Chakhmakhcheva, O.G. et al. Monomers containing 2′-O-alkoxymethyl groups as synthons for the oligonucleotide synthesis by the phosphotriester method. Russ J Bioorg Chem 37, 586–592 (2011). https://doi.org/10.1134/S1068162011050025

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  • DOI: https://doi.org/10.1134/S1068162011050025

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