Dipentafluorophenyl carbonate--a reagent for the synthesis of oligonucleotides and their conjugates.
Identifieur interne : 004523 ( Main/Curation ); précédent : 004522; suivant : 004524Dipentafluorophenyl carbonate--a reagent for the synthesis of oligonucleotides and their conjugates.
Auteurs : V A Efimov [Russie] ; A L Kalinkina ; O G ChakhmakhchevaSource :
- Nucleic acids research [ 0305-1048 ] ; 1993.
Descripteurs français
- KwdFr :
- MESH :
English descriptors
- KwdEn :
- MESH :
- chemical , chemical synthesis : Oligodeoxyribonucleotides.
- chemical , chemistry : Fluorocarbons, Oligodeoxyribonucleotides, Organophosphonates.
- Base Sequence, Molecular Sequence Data.
Abstract
Dipentafluorophenyl carbonate has been successfully used as condensing agent for the internucleotide bond formation in the synthesis of oligonucleotides via H-phosphonate approach. The mechanism of a nucleotide component activation with this reagent has been investigated with the help of 31P NMR spectroscopy. It was shown that preactivation of deoxynucleoside H-phosphonate with dipentafluorophenyl carbonate has no influence on the efficiency of the synthesis. This reagent is highly reactive, nonhygroscopic and stable on storage at room temperature. The effectiveness of dipentafluorophenyl carbonate in the oligonucleotide chemistry has been demonstrated in the solid-phase synthesis of 10-50-mers on 0.2, 1 and 10 mumol scales. The use of this reagent for the derivatisation of polymer supports as well as for the synthesis of oligonucleotide conjugates with polyethylene glycol and a lipid is described.
DOI: 10.1093/nar/21.23.5337
PubMed: 8265346
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<country>Russie</country>
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<wicri:orgArea>Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences</wicri:orgArea>
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<author><name sortKey="Kalinkina, A L" sort="Kalinkina, A L" uniqKey="Kalinkina A" first="A L" last="Kalinkina">A L Kalinkina</name>
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<affiliation wicri:level="3"><nlm:affiliation>Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow.</nlm:affiliation>
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<placeName><settlement type="city">Moscou</settlement>
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<author><name sortKey="Chakhmakhcheva, O G" sort="Chakhmakhcheva, O G" uniqKey="Chakhmakhcheva O" first="O G" last="Chakhmakhcheva">O G Chakhmakhcheva</name>
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<series><title level="j">Nucleic acids research</title>
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<term>Oligodeoxyribonucleotides (chemical synthesis)</term>
<term>Oligodeoxyribonucleotides (chemistry)</term>
<term>Organophosphonates (chemistry)</term>
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<keywords scheme="KwdFr" xml:lang="fr"><term>Données de séquences moléculaires</term>
<term>Fluorocarbones ()</term>
<term>Oligodésoxyribonucléotides ()</term>
<term>Oligodésoxyribonucléotides (synthèse chimique)</term>
<term>Phosphonates ()</term>
<term>Séquence nucléotidique</term>
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<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Oligodeoxyribonucleotides</term>
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<term>Oligodeoxyribonucleotides</term>
<term>Organophosphonates</term>
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<keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Oligodésoxyribonucléotides</term>
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<term>Molecular Sequence Data</term>
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<term>Fluorocarbones</term>
<term>Oligodésoxyribonucléotides</term>
<term>Phosphonates</term>
<term>Séquence nucléotidique</term>
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<front><div type="abstract" xml:lang="en">Dipentafluorophenyl carbonate has been successfully used as condensing agent for the internucleotide bond formation in the synthesis of oligonucleotides via H-phosphonate approach. The mechanism of a nucleotide component activation with this reagent has been investigated with the help of 31P NMR spectroscopy. It was shown that preactivation of deoxynucleoside H-phosphonate with dipentafluorophenyl carbonate has no influence on the efficiency of the synthesis. This reagent is highly reactive, nonhygroscopic and stable on storage at room temperature. The effectiveness of dipentafluorophenyl carbonate in the oligonucleotide chemistry has been demonstrated in the solid-phase synthesis of 10-50-mers on 0.2, 1 and 10 mumol scales. The use of this reagent for the derivatisation of polymer supports as well as for the synthesis of oligonucleotide conjugates with polyethylene glycol and a lipid is described.</div>
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