Phosphonate

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Mohamed Abarbri - One of the best experts on this subject based on the ideXlab platform.

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Anne-sophie Mora - One of the best experts on this subject based on the ideXlab platform.

Ivan Rosenberg - One of the best experts on this subject based on the ideXlab platform.

  • Solid-Phase Synthesis of Phosphorothioate/Phosphonothioate and Phosphoramidate/Phosphonamidate Oligonucleotides
    MDPI AG, 2019
    Co-Authors: Ondřej Kostov, Ondřej Páv, Radek Liboska, Pavel Novák, Ivan Rosenberg
    Abstract:

    We have developed a robust solid-phase protocol which allowed the synthesis of chimeric oligonucleotides modified with phosphodiester and O-methylPhosphonate linkages as well as their P-S and P-N variants. The novel O-methylPhosphonate-derived modifications were obtained by oxidation, sulfurization, and amidation of the O-methyl-(H)-phosphinate internucleotide linkage introduced into the oligonucleotide chain by H-Phosphonate chemistry using nucleoside-O-methyl-(H)-phosphinates as monomers. The H-Phosphonate coupling followed by oxidation after each cycle enabled us to successfully combine H-Phosphonate and phosphoramidite chemistries to synthesize diversely modified oligonucleotide strands

  • 4-Toluenesulfonyloxymethyl-(H)-phosphinate: A Reagent for the Introduction of O- and S-Methyl-(H)-phosphinate Moieties.
    Organic letters, 2016
    Co-Authors: Ondřej Kostov, Ondřej Páv, Miloš Buděšínský, Radek Liboska, Ondřej Šimák, Magdalena Petrová, Pavel Novák, Ivan Rosenberg
    Abstract:

    The straightforward synthesis of sodium 4-toluenesulfonyloxymethyl-(H)-phosphinate and (H)-phosphinomethylisothiouronium tosylate as new reagents for the preparation of O- and S-methyl-(H)-phosphinic acid derivatives, respectively, is described. The reactivity of both reagents was demonstrated by the preparation of protected 2′-deoxyribonucleoside-O-methyl-(H)-phosphinates in the 5′- and 3′-series and 2′,5′-dideoxyribonucleoside-5′-S-methyl-(H)-phosphinates. These compounds represent a new class of monomers compatible with the solid phase synthesis of oligonucleotides by H-Phosphonate chemistry, as it was proved with the synthesis of a fully Phosphonate heptamer.