Solid phase synthesis of oligodeoxyribonucleoside phosphorodithioates from thiophosphoramidites.
Identifieur interne : 000690 ( Ncbi/Merge ); précédent : 000689; suivant : 000691Solid phase synthesis of oligodeoxyribonucleoside phosphorodithioates from thiophosphoramidites.
Auteurs : K. Bjerg Rde [Danemark] ; O. DahlSource :
- Nucleic acids research [ 0305-1048 ] ; 1991.
Descripteurs français
- KwdFr :
- Chromatographie en phase liquide à haute performance, Composés organothiophosphorés (), Concentration en ions d'hydrogène, Données de séquences moléculaires, Oligodésoxyribonucléotides (isolement et purification), Oligodésoxyribonucléotides (synthèse chimique), Spectroscopie par résonance magnétique, Séquence nucléotidique, Température, Thionucléotides (isolement et purification), Thionucléotides (synthèse chimique), Électrophorèse sur gel de polyacrylamide.
- MESH :
- isolement et purification : Oligodésoxyribonucléotides, Thionucléotides.
- synthèse chimique : Oligodésoxyribonucléotides, Thionucléotides.
- Chromatographie en phase liquide à haute performance, Composés organothiophosphorés, Concentration en ions d'hydrogène, Données de séquences moléculaires, Spectroscopie par résonance magnétique, Séquence nucléotidique, Température, Électrophorèse sur gel de polyacrylamide.
English descriptors
- KwdEn :
- Base Sequence, Chromatography, High Pressure Liquid, Electrophoresis, Polyacrylamide Gel, Hydrogen-Ion Concentration, Magnetic Resonance Spectroscopy, Molecular Sequence Data, Oligodeoxyribonucleotides (chemical synthesis), Oligodeoxyribonucleotides (isolation & purification), Organothiophosphorus Compounds (chemistry), Temperature, Thionucleotides (chemical synthesis), Thionucleotides (isolation & purification).
- MESH :
- chemical , chemical synthesis : Oligodeoxyribonucleotides, Thionucleotides.
- chemical , chemistry : Organothiophosphorus Compounds.
- chemical , isolation & purification : Oligodeoxyribonucleotides, Thionucleotides.
- Base Sequence, Chromatography, High Pressure Liquid, Electrophoresis, Polyacrylamide Gel, Hydrogen-Ion Concentration, Magnetic Resonance Spectroscopy, Molecular Sequence Data, Temperature.
Abstract
Oligonucleoside phosphorodithioates 1 are modified DNA sequences with potential use as antisense oligonucleotides. The preparation of up to 20-mers containing all four bases by solid phase synthesis is described, with details on the preparation of the four monomer units (protected nucleoside thiophosphoramidites 2), the conditions used for the assembly of the strands with up to 19 phosphorodithioate linkages, and the purification and characterisation of the products. Full-length homogeneity of HPLC-purified all-phosphorodithioate products is demonstrated by PAGE, but 31P NMR discloses the presence of phosphorothioate impurities (typically 8-9%), the origin of which is discussed. Oligonucleoside phosphorodithioates are freely soluble in water at neutral or basic pH, and are very stable towards oxidation, hydrolysis, and nuclease cleavage. Their ability to hybridize to complementary DNA has been studied by UV melting point (Tm) measurements. The observed depression of Tm, 0.5-2 degrees C per phosphorodithioate linkage, is higher that the 0.4-0.6 degrees C found for phosphorothioates.
DOI: 10.1093/nar/19.21.5843
PubMed: 1945874
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pubmed:1945874Le document en format XML
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<affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, HC Orsted Institute, University of Copenhagen, Denmark.</nlm:affiliation>
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<wicri:regionArea>Department of Chemistry, HC Orsted Institute, University of Copenhagen</wicri:regionArea>
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<author><name sortKey="Dahl, O" sort="Dahl, O" uniqKey="Dahl O" first="O" last="Dahl">O. Dahl</name>
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<term>Chromatography, High Pressure Liquid</term>
<term>Electrophoresis, Polyacrylamide Gel</term>
<term>Hydrogen-Ion Concentration</term>
<term>Magnetic Resonance Spectroscopy</term>
<term>Molecular Sequence Data</term>
<term>Oligodeoxyribonucleotides (chemical synthesis)</term>
<term>Oligodeoxyribonucleotides (isolation & purification)</term>
<term>Organothiophosphorus Compounds (chemistry)</term>
<term>Temperature</term>
<term>Thionucleotides (chemical synthesis)</term>
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<keywords scheme="KwdFr" xml:lang="fr"><term>Chromatographie en phase liquide à haute performance</term>
<term>Composés organothiophosphorés ()</term>
<term>Concentration en ions d'hydrogène</term>
<term>Données de séquences moléculaires</term>
<term>Oligodésoxyribonucléotides (isolement et purification)</term>
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<term>Spectroscopie par résonance magnétique</term>
<term>Séquence nucléotidique</term>
<term>Température</term>
<term>Thionucléotides (isolement et purification)</term>
<term>Thionucléotides (synthèse chimique)</term>
<term>Électrophorèse sur gel de polyacrylamide</term>
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<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Oligodeoxyribonucleotides</term>
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<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Organothiophosphorus Compounds</term>
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<keywords scheme="MESH" type="chemical" qualifier="isolation & purification" xml:lang="en"><term>Oligodeoxyribonucleotides</term>
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<keywords scheme="MESH" qualifier="isolement et purification" xml:lang="fr"><term>Oligodésoxyribonucléotides</term>
<term>Thionucléotides</term>
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<keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Oligodésoxyribonucléotides</term>
<term>Thionucléotides</term>
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<term>Chromatography, High Pressure Liquid</term>
<term>Electrophoresis, Polyacrylamide Gel</term>
<term>Hydrogen-Ion Concentration</term>
<term>Magnetic Resonance Spectroscopy</term>
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<term>Temperature</term>
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<term>Composés organothiophosphorés</term>
<term>Concentration en ions d'hydrogène</term>
<term>Données de séquences moléculaires</term>
<term>Spectroscopie par résonance magnétique</term>
<term>Séquence nucléotidique</term>
<term>Température</term>
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<front><div type="abstract" xml:lang="en">Oligonucleoside phosphorodithioates 1 are modified DNA sequences with potential use as antisense oligonucleotides. The preparation of up to 20-mers containing all four bases by solid phase synthesis is described, with details on the preparation of the four monomer units (protected nucleoside thiophosphoramidites 2), the conditions used for the assembly of the strands with up to 19 phosphorodithioate linkages, and the purification and characterisation of the products. Full-length homogeneity of HPLC-purified all-phosphorodithioate products is demonstrated by PAGE, but 31P NMR discloses the presence of phosphorothioate impurities (typically 8-9%), the origin of which is discussed. Oligonucleoside phosphorodithioates are freely soluble in water at neutral or basic pH, and are very stable towards oxidation, hydrolysis, and nuclease cleavage. Their ability to hybridize to complementary DNA has been studied by UV melting point (Tm) measurements. The observed depression of Tm, 0.5-2 degrees C per phosphorodithioate linkage, is higher that the 0.4-0.6 degrees C found for phosphorothioates.</div>
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<Abstract><AbstractText>Oligonucleoside phosphorodithioates 1 are modified DNA sequences with potential use as antisense oligonucleotides. The preparation of up to 20-mers containing all four bases by solid phase synthesis is described, with details on the preparation of the four monomer units (protected nucleoside thiophosphoramidites 2), the conditions used for the assembly of the strands with up to 19 phosphorodithioate linkages, and the purification and characterisation of the products. Full-length homogeneity of HPLC-purified all-phosphorodithioate products is demonstrated by PAGE, but 31P NMR discloses the presence of phosphorothioate impurities (typically 8-9%), the origin of which is discussed. Oligonucleoside phosphorodithioates are freely soluble in water at neutral or basic pH, and are very stable towards oxidation, hydrolysis, and nuclease cleavage. Their ability to hybridize to complementary DNA has been studied by UV melting point (Tm) measurements. The observed depression of Tm, 0.5-2 degrees C per phosphorodithioate linkage, is higher that the 0.4-0.6 degrees C found for phosphorothioates.</AbstractText>
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<ReferenceList><Reference><Citation>Nucleic Acids Res. 1987 Dec 10;15(23):9921-32</Citation>
<ArticleIdList><ArticleId IdType="pubmed">3480505</ArticleId>
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<Reference><Citation>Ciba Found Symp. 1991;158:158-66; discussion 166-8</Citation>
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<Reference><Citation>Nucleic Acids Res. 1991 Apr 11;19(7):1527-32</Citation>
<ArticleIdList><ArticleId IdType="pubmed">2027761</ArticleId>
</ArticleIdList>
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<Reference><Citation>Nucleic Acids Res. 1990 Dec 25;18(24):7279-86</Citation>
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