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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)
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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MDPI and ACS Style

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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