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Synthesis of Pentaerythritol-Based Branching Reagents for Modification of Proteins and Nucleic Acids by [2+3] Dipolar Cycloaddition Reaction

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Abstract

Alkylation of pentaerythritol symmetrically substituted with propylene glycol with propargyl bromide afforded compounds containing two or three alkyne moieties. Amidophosphite reagents and solid supports were prepared for the introduction of two and three acetylene fragments into oligonucleotides at the 3'- and 5'-positions and inside the chain under conditions of automated solid-phase oligonucleotide synthesis. Based on the trialkynyl derivative, an N-hydroxysuccinimide ester was obtained which can be used to modify biomolecules attacking the amino group. Conjugates obtained can be used for multiple modifications by [3+2] dipolar cycloaddition reaction.

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Authors and Affiliations

  1. Institute of Physical Organic Chemistry of the National Academy of Sciences of Belarus, ul. Surganova 13, Minsk, 220072, Belarus

    Yu. V. Martynenko-Makaev, V. V. Udodova, O. L. Sharko & V. V. Shmanai

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  1. Yu. V. Martynenko-Makaev
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  2. V. V. Udodova
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  3. O. L. Sharko
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  4. V. V. Shmanai
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Correspondence to Yu. V. Martynenko-Makaev.

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Original Russian Text © Yu.V. Martynenko-Makaev, V.V. Udodova, O.L. Sharko, V.V. Shmanai, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 3, pp. 425–433.

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Martynenko-Makaev, Y.V., Udodova, V.V., Sharko, O.L. et al. Synthesis of Pentaerythritol-Based Branching Reagents for Modification of Proteins and Nucleic Acids by [2+3] Dipolar Cycloaddition Reaction. Russ J Gen Chem 88, 452–461 (2018). https://doi.org/10.1134/S1070363218030118

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  • DOI: https://doi.org/10.1134/S1070363218030118

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