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Solid-Phase Synthesis of Phosphorothioate/Phosphonothioate and Phosphoramidate/Phosphonamidate Oligonucleotides
O. Kostov, R. Liboska, O. Páv, P. Novák, I. Rosenberg,
Language English Country Switzerland
Document type Journal Article
Grant support
17-12703S
Grantová Agentura České Republiky
NLK
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- MeSH
- Amides chemistry MeSH
- Dimerization MeSH
- Phosphates chemistry MeSH
- Phosphorothioate Oligonucleotides chemical synthesis MeSH
- Phosphoric Acids chemistry MeSH
- Molecular Structure MeSH
- Oligonucleotides chemical synthesis chemistry MeSH
- Solid-Phase Synthesis Techniques * MeSH
- Publication type
- Journal Article MeSH
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.
References provided by Crossref.org
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- $a Kostov, Ondřej $u Institute of Organic Chemistry and Biochemistry AS CR, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic. kostov@uochb.cas.cz.
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- $a Solid-Phase Synthesis of Phosphorothioate/Phosphonothioate and Phosphoramidate/Phosphonamidate Oligonucleotides / $c O. Kostov, R. Liboska, O. Páv, P. Novák, I. Rosenberg,
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- $a 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.
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- $a Liboska, Radek $u Institute of Organic Chemistry and Biochemistry AS CR, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic. liboska@uochb.cas.cz.
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- $a Páv, Ondřej $u Institute of Organic Chemistry and Biochemistry AS CR, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic. pav@uochb.cas.cz.
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- $a Rosenberg, Ivan $u Institute of Organic Chemistry and Biochemistry AS CR, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic. rosenberg@uochb.cas.cz.
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