Solid phase synthesis of oligodeoxyribonucleoside phosphorodithioates from thiophosphoramidites.
Identifieur interne : 002824 ( PubMed/Checkpoint ); précédent : 002823; suivant : 002825Solid 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
Affiliations:
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Dahl</name></author></analytic><series><title level="j">Nucleic acids research</title><idno type="ISSN">0305-1048</idno><imprint><date when="1991" type="published">1991</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Base Sequence</term><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><term>Thionucleotides (isolation & purification)</term></keywords><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><term>Oligodésoxyribonucléotides (synthèse chimique)</term><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></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Oligodeoxyribonucleotides</term><term>Thionucleotides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Organothiophosphorus Compounds</term></keywords><keywords scheme="MESH" type="chemical" qualifier="isolation & purification" xml:lang="en"><term>Oligodeoxyribonucleotides</term><term>Thionucleotides</term></keywords><keywords scheme="MESH" qualifier="isolement et purification" xml:lang="fr"><term>Oligodésoxyribonucléotides</term><term>Thionucléotides</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Oligodésoxyribonucléotides</term><term>Thionucléotides</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Base Sequence</term><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>Temperature</term></keywords><keywords scheme="MESH" 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>Spectroscopie par résonance magnétique</term><term>Séquence nucléotidique</term><term>Température</term><term>Électrophorèse sur gel de polyacrylamide</term></keywords></textClass></profileDesc></teiHeader><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></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">1945874</PMID><DateCompleted><Year>1991</Year><Month>12</Month><Day>17</Day></DateCompleted><DateRevised><Year>2019</Year><Month>05</Month><Day>01</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0305-1048</ISSN><JournalIssue CitedMedium="Print"><Volume>19</Volume><Issue>21</Issue><PubDate><Year>1991</Year><Month>Nov</Month><Day>11</Day></PubDate></JournalIssue><Title>Nucleic acids research</Title><ISOAbbreviation>Nucleic Acids Res.</ISOAbbreviation></Journal><ArticleTitle>Solid phase synthesis of oligodeoxyribonucleoside phosphorodithioates from thiophosphoramidites.</ArticleTitle><Pagination><MedlinePgn>5843-50</MedlinePgn></Pagination><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. 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Dahl</name></noCountry><country name="Danemark"><noRegion><name sortKey="Bjerg Rde, K" sort="Bjerg Rde, K" uniqKey="Bjerg Rde K" first="K" last="Bjerg Rde">K. Bjerg Rde</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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