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A convenient method for the synthesis of phosphoramidite non-nucleotide inserts for preparation of functionalized oligonucleotides

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Abstract

A simple approach to the synthesis of amidophosphite synthons of achiral non-nucleotide inserts using 4-(2-(4,4′-dimethoxytrityloxy)ethyl)morpholine-2,3-dione as a backbone of key precursor was suggested. Non-nucleotide synthons were synthesized using this approach that were suitable for synthesis of acridine-containing oligonucleotide derivatives, as well as oligonucleotides with branched carbohydrate-phosphate backbone.

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Abbreviations

TBDMS:

tret-butyldimethylsilyl

DMTr:

dimethoxytrityl

CEP:

2-cyanoethoxy diisopropylamino phosphinyl

Lev:

levulinyl

DIPEA:

diisopropylethylamine

TEA:

triethylamine

DMAP:

4-N,N-dimethylaminopyridine

References

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Correspondence to D. V. Pyshnyi.

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Original Russian Text © M.S. Kupryushkin, D.V. Pyshnyi, 2012, published in Bioorganicheskaya Khimiya, 2012, Vol. 38, No. 6, pp. 745–750.

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Kupryushkin, M.S., Pyshnyi, D.V. A convenient method for the synthesis of phosphoramidite non-nucleotide inserts for preparation of functionalized oligonucleotides. Russ J Bioorg Chem 38, 662–666 (2012). https://doi.org/10.1134/S1068162012060106

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  • DOI: https://doi.org/10.1134/S1068162012060106

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