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N-azidomethylbenzoyl blocking group in the phosphotriester synthesis of oligoribonucleotides

Abstract

An effective modification of the phosphotriester method has been developed for the automatic synthesis of DNA and RNA fragments using O-nucleophilic intramolecular catalysis and the 2-(azidomethyl)benzoyl group for the protection of the amino groups of nucleotide heterocyclic bases.

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Abbreviations

AZM:

azidomethyl

AZMB:

o-azidomethylben-zoyl

DBU:

1,8-diazabicyclo[5.4.0]undec-7-ene

DMTr:

4,4′-dimethoxytrityl

NBS:

2-nitrobenzenesulfenyl

TEAB:

triethyl-ammonium bicarbonate

TMS:

trimethylsilyl

TPS:

2,4,6-tri-isopropylbenzenesulfonyl

TIPDS-C12 :

1,3-Dichloro-1,1,3,3-tetraisopropyldisiloxane

TBAF:

tetrabutylammonium fluoride

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Correspondence to V. A. Efimov.

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Original Russian Text © V.A. Efimov, A.V. Aralov, S.A. Grachev, O.G. Chakhmakhcheva, 2010, published in Bioorganicheskaya Khimiya, 2010, Vol. 36, No. 5, pp. 681–687.

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Efimov, V.A., Aralov, A.V., Grachev, S.A. et al. N-azidomethylbenzoyl blocking group in the phosphotriester synthesis of oligoribonucleotides. Russ J Bioorg Chem 36, 628–633 (2010). https://doi.org/10.1134/S1068162010050110

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  • DOI: https://doi.org/10.1134/S1068162010050110

Key words

  • 2-azidomethylbenzoyl group
  • intramolecular catalysis
  • oligonucleotides synthesis
  • phosphotriester method