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Synthesis and properties of photolabile (caged) phosphotriester derivatives of dinucleoside phosphates

Abstract

Dinucleoside phosphates that harbor phosphate groups transiently blocked (caged) byo-nitrobenzyl oro-nitroveratryl residues were synthesized. It was shown that the conditions of the UV-induced deprotection largely depend on the nature of the protective group. The phosphotriesters obtained were resistant toward snake venom phosphodiesterase and nucleases of the cellular extract. The synthesis of the dinucleoside phosphates containing a photolabile group preceeded the incorporation of the modified blocks into extended oligonucleotides by the phosphoramidite method.

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Abbreviations

DMTr:

dimethoxytrityl

Lev:

levulinyl

TPS:

triisopropylbenzenesulfonyl

PhCl:

p-chlorophenyl

MeIm:

N-methylimidazole

VPDE:

snake venom phosphodiesterase

PEG:

polyethyleneglycol

TBAF:

tetrabutylammonium fluoride

Tri:

1,2,4-triazole

RPC:

reverse-phase chromatography. Prefix “d” for deoxyribooligonucleotides is omitted

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Correspondence to T. V. Abramova.

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Abramova, T.V., Leonetti, J.P., Vlassov, V.V. et al. Synthesis and properties of photolabile (caged) phosphotriester derivatives of dinucleoside phosphates. Russ J Bioorg Chem 26, 174–182 (2000). https://doi.org/10.1007/BF02786343

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  • DOI: https://doi.org/10.1007/BF02786343

Key words

  • oligonucleotide derivatives
  • photolabile compounds