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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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