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

0506739 - ÚOCHB 2020 RIV CH eng J - Článek v odborném periodiku
Kostov, Ondřej - Liboska, Radek - Páv, Ondřej - Novák, Pavel - Rosenberg, Ivan
Solid-Phase Synthesis of Phosphorothioate/Phosphonothioate and Phosphoramidate/Phosphonamidate Oligonucleotides.
Molecules. Roč. 24, č. 10 (2019), č. článku 1872. E-ISSN 1420-3049
Grant CEP: GA ČR(CZ) GA17-12703S
Institucionální podpora: RVO:61388963
Klíčová slova: H-phosphinate * H-phosphonate * phosphoramidite * oligonucleotide * phosphonate * phosphorothioate * phosphonothioate * phosphoramidate * phosphonamidate
Obor OECD: Organic chemistry
Impakt faktor: 3.267, rok: 2019
Způsob publikování: Open access
https://www.mdpi.com/1420-3049/24/10/1872/htm

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.
Trvalý link: http://hdl.handle.net/11104/0297927