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Solid-Phase Synthesis of Phosphorothioate/Phosphonothioate and Phosphoramidate/Phosphonamidate Oligonucleotides

Institute of Organic Chemistry and Biochemistry AS CR, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic
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Molecules 2019, 24(10), 1872; https://doi.org/10.3390/molecules24101872
Received: 1 May 2019 / Revised: 9 May 2019 / Accepted: 14 May 2019 / Published: 15 May 2019
(This article belongs to the Special Issue Antisense Oligonucleotide Chemistry and Applications)
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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. View Full-Text
Keywords: H-phosphinate; H-phosphonate; phosphoramidite; oligonucleotide; phosphonate; phosphorothioate; phosphonothioate; phosphoramidate; phosphonamidate H-phosphinate; H-phosphonate; phosphoramidite; oligonucleotide; phosphonate; phosphorothioate; phosphonothioate; phosphoramidate; phosphonamidate
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Kostov, O.; Liboska, R.; Páv, O.; Novák, P.; Rosenberg, I. Solid-Phase Synthesis of Phosphorothioate/Phosphonothioate and Phosphoramidate/Phosphonamidate Oligonucleotides. Molecules 2019, 24, 1872.

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