alpha-L-ribo-configured locked nucleic acid (alpha-L-LNA): synthesis and properties.
Identifieur interne : 003304 ( Main/Exploration ); précédent : 003303; suivant : 003305alpha-L-ribo-configured locked nucleic acid (alpha-L-LNA): synthesis and properties.
Auteurs : Mads D. S Rensen [Danemark] ; Lisbet Kvaern ; Torsten Bryld ; Anders E. H Kansson ; Birgit Verbeure ; Gilles Gaubert ; Piet Herdewijn ; Jesper WengelSource :
- Journal of the American Chemical Society [ 0002-7863 ] ; 2002.
Descripteurs français
- KwdFr :
- Acides nucléiques (), Acides nucléiques (synthèse chimique), Composés organiques du phosphore (), Composés organiques du phosphore (synthèse chimique), Conformation moléculaire, Dichroïsme circulaire, Escherichia coli (enzymologie), Nucléoside purique (), Nucléoside purique (synthèse chimique), Nucléosides pyrimidiques (), Nucléosides pyrimidiques (synthèse chimique), Phosphodiesterase I, Phosphodiesterases (), Ribonuclease H (), Température élevée.
- MESH :
- enzymologie : Escherichia coli.
- synthèse chimique : Acides nucléiques, Composés organiques du phosphore, Nucléoside purique, Nucléosides pyrimidiques.
- Acides nucléiques, Composés organiques du phosphore, Conformation moléculaire, Dichroïsme circulaire, Nucléoside purique, Nucléosides pyrimidiques, Phosphodiesterase I, Phosphodiesterases, Ribonuclease H, Température élevée.
English descriptors
- KwdEn :
- Circular Dichroism, Escherichia coli (enzymology), Hot Temperature, Molecular Conformation, Nucleic Acids (chemical synthesis), Nucleic Acids (chemistry), Organophosphorus Compounds (chemical synthesis), Organophosphorus Compounds (chemistry), Phosphodiesterase I, Phosphoric Diester Hydrolases (chemistry), Purine Nucleosides (chemical synthesis), Purine Nucleosides (chemistry), Pyrimidine Nucleosides (chemical synthesis), Pyrimidine Nucleosides (chemistry), Ribonuclease H (chemistry).
- MESH :
- chemical , chemical synthesis : Nucleic Acids, Organophosphorus Compounds, Purine Nucleosides, Pyrimidine Nucleosides.
- chemical , chemistry : Nucleic Acids, Organophosphorus Compounds, Phosphoric Diester Hydrolases, Purine Nucleosides, Pyrimidine Nucleosides, Ribonuclease H.
- enzymology : Escherichia coli.
- Circular Dichroism, Hot Temperature, Molecular Conformation, Phosphodiesterase I.
Abstract
The syntheses of monomeric nucleosides and 3'-O-phosphoramidite building blocks en route to alpha-L-ribo-configured locked nucleic acids (alpha-L-LNA), composed entirely of alpha-L-LNA monomers (alpha-L-ribo configuration) or of a mixture of alpha-L-LNA and DNA monomers (beta-D-ribo configuration), are described and the alpha-L-LNA oligomers are studied. Bicyclic 5-methylcytosin-1-yl and adenine-9-yl nucleoside derivatives have been prepared and the phosphoramidite approach has been used for the automated oligomerization leading to alpha-L-LNA oligomers. Binding studies revealed very efficient recognition of single-stranded DNA and RNA target oligonucleotide strands. Thus, stereoirregular alpha-L-LNA 11-mers containing a mixture of alpha-L-LNA monomers and DNA monomers ("mix-mer alpha-L-LNA") were shown to display DeltaT(m) values of +1 to +3 degrees C per modification toward DNA and +4 to +5 degrees C toward RNA when compared with the corresponding unmodified DNA x DNA and DNA x RNA reference duplexes. The corresponding DeltaT(m) values per modification for the stereoregular fully modified alpha-L-LNA were determined to be +4 degrees C (against DNA) and +5 degrees C (against RNA). 11-Mer alpha-L-LNAs (mix-mer alpha- L-LNA or fully modified alpha- L-LNA) were shown in vitro to be significantly stabilized toward 3'-exonucleolytic degradation. A duplex formed between RNA and either mix-mer alpha-L-LNA or fully modified alpha-L-LNA induced in vitro Escherichia coli RNase H-mediated cleavage, albeit very slow, of the RNA targets at high enzyme concentrations.
DOI: 10.1021/ja0168763
PubMed: 11878970
Affiliations:
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Le document en format XML
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S Rensen</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen, Denmark.</nlm:affiliation><country xml:lang="fr">Danemark</country><wicri:regionArea>Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen</wicri:regionArea><wicri:noRegion>DK-2100 Copenhagen</wicri:noRegion></affiliation></author><author><name sortKey="Kvaern, Lisbet" sort="Kvaern, Lisbet" uniqKey="Kvaern L" first="Lisbet" last="Kvaern">Lisbet Kvaern</name></author><author><name sortKey="Bryld, Torsten" sort="Bryld, Torsten" uniqKey="Bryld T" first="Torsten" last="Bryld">Torsten Bryld</name></author><author><name sortKey="H Kansson, Anders E" sort="H Kansson, Anders E" uniqKey="H Kansson A" first="Anders E" last="H Kansson">Anders E. H Kansson</name></author><author><name sortKey="Verbeure, Birgit" sort="Verbeure, Birgit" uniqKey="Verbeure B" first="Birgit" last="Verbeure">Birgit Verbeure</name></author><author><name sortKey="Gaubert, Gilles" sort="Gaubert, Gilles" uniqKey="Gaubert G" first="Gilles" last="Gaubert">Gilles Gaubert</name></author><author><name sortKey="Herdewijn, Piet" sort="Herdewijn, Piet" uniqKey="Herdewijn P" first="Piet" last="Herdewijn">Piet Herdewijn</name></author><author><name sortKey="Wengel, Jesper" sort="Wengel, Jesper" uniqKey="Wengel J" first="Jesper" last="Wengel">Jesper Wengel</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2002">2002</date><idno type="RBID">pubmed:11878970</idno><idno type="pmid">11878970</idno><idno type="doi">10.1021/ja0168763</idno><idno type="wicri:Area/PubMed/Corpus">002516</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">002516</idno><idno type="wicri:Area/PubMed/Curation">002516</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">002516</idno><idno type="wicri:Area/PubMed/Checkpoint">002342</idno><idno type="wicri:explorRef" wicri:stream="Checkpoint" wicri:step="PubMed">002342</idno><idno type="wicri:Area/Ncbi/Merge">000130</idno><idno type="wicri:Area/Ncbi/Curation">000130</idno><idno type="wicri:Area/Ncbi/Checkpoint">000130</idno><idno type="wicri:doubleKey">0002-7863:2002:S Rensen M:alpha:l:ribo</idno><idno type="wicri:Area/Main/Merge">003339</idno><idno type="wicri:Area/Main/Curation">003304</idno><idno type="wicri:Area/Main/Exploration">003304</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">alpha-L-ribo-configured locked nucleic acid (alpha-L-LNA): synthesis and properties.</title><author><name sortKey="S Rensen, Mads D" sort="S Rensen, Mads D" uniqKey="S Rensen M" first="Mads D" last="S Rensen">Mads D. S Rensen</name><affiliation wicri:level="1"><nlm:affiliation>Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen, Denmark.</nlm:affiliation><country xml:lang="fr">Danemark</country><wicri:regionArea>Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen</wicri:regionArea><wicri:noRegion>DK-2100 Copenhagen</wicri:noRegion></affiliation></author><author><name sortKey="Kvaern, Lisbet" sort="Kvaern, Lisbet" uniqKey="Kvaern L" first="Lisbet" last="Kvaern">Lisbet Kvaern</name></author><author><name sortKey="Bryld, Torsten" sort="Bryld, Torsten" uniqKey="Bryld T" first="Torsten" last="Bryld">Torsten Bryld</name></author><author><name sortKey="H Kansson, Anders E" sort="H Kansson, Anders E" uniqKey="H Kansson A" first="Anders E" last="H Kansson">Anders E. H Kansson</name></author><author><name sortKey="Verbeure, Birgit" sort="Verbeure, Birgit" uniqKey="Verbeure B" first="Birgit" last="Verbeure">Birgit Verbeure</name></author><author><name sortKey="Gaubert, Gilles" sort="Gaubert, Gilles" uniqKey="Gaubert G" first="Gilles" last="Gaubert">Gilles Gaubert</name></author><author><name sortKey="Herdewijn, Piet" sort="Herdewijn, Piet" uniqKey="Herdewijn P" first="Piet" last="Herdewijn">Piet Herdewijn</name></author><author><name sortKey="Wengel, Jesper" sort="Wengel, Jesper" uniqKey="Wengel J" first="Jesper" last="Wengel">Jesper Wengel</name></author></analytic><series><title level="j">Journal of the American Chemical Society</title><idno type="ISSN">0002-7863</idno><imprint><date when="2002" type="published">2002</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Circular Dichroism</term><term>Escherichia coli (enzymology)</term><term>Hot Temperature</term><term>Molecular Conformation</term><term>Nucleic Acids (chemical synthesis)</term><term>Nucleic Acids (chemistry)</term><term>Organophosphorus Compounds (chemical synthesis)</term><term>Organophosphorus Compounds (chemistry)</term><term>Phosphodiesterase I</term><term>Phosphoric Diester Hydrolases (chemistry)</term><term>Purine Nucleosides (chemical synthesis)</term><term>Purine Nucleosides (chemistry)</term><term>Pyrimidine Nucleosides (chemical synthesis)</term><term>Pyrimidine Nucleosides (chemistry)</term><term>Ribonuclease H (chemistry)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Acides nucléiques ()</term><term>Acides nucléiques (synthèse chimique)</term><term>Composés organiques du phosphore ()</term><term>Composés organiques du phosphore (synthèse chimique)</term><term>Conformation moléculaire</term><term>Dichroïsme circulaire</term><term>Escherichia coli (enzymologie)</term><term>Nucléoside purique ()</term><term>Nucléoside purique (synthèse chimique)</term><term>Nucléosides pyrimidiques ()</term><term>Nucléosides pyrimidiques (synthèse chimique)</term><term>Phosphodiesterase I</term><term>Phosphodiesterases ()</term><term>Ribonuclease H ()</term><term>Température élevée</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Nucleic Acids</term><term>Organophosphorus Compounds</term><term>Purine Nucleosides</term><term>Pyrimidine Nucleosides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Nucleic Acids</term><term>Organophosphorus Compounds</term><term>Phosphoric Diester Hydrolases</term><term>Purine Nucleosides</term><term>Pyrimidine Nucleosides</term><term>Ribonuclease H</term></keywords><keywords scheme="MESH" qualifier="enzymologie" xml:lang="fr"><term>Escherichia coli</term></keywords><keywords scheme="MESH" qualifier="enzymology" xml:lang="en"><term>Escherichia coli</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Acides nucléiques</term><term>Composés organiques du phosphore</term><term>Nucléoside purique</term><term>Nucléosides pyrimidiques</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Circular Dichroism</term><term>Hot Temperature</term><term>Molecular Conformation</term><term>Phosphodiesterase I</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Acides nucléiques</term><term>Composés organiques du phosphore</term><term>Conformation moléculaire</term><term>Dichroïsme circulaire</term><term>Nucléoside purique</term><term>Nucléosides pyrimidiques</term><term>Phosphodiesterase I</term><term>Phosphodiesterases</term><term>Ribonuclease H</term><term>Température élevée</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The syntheses of monomeric nucleosides and 3'-O-phosphoramidite building blocks en route to alpha-L-ribo-configured locked nucleic acids (alpha-L-LNA), composed entirely of alpha-L-LNA monomers (alpha-L-ribo configuration) or of a mixture of alpha-L-LNA and DNA monomers (beta-D-ribo configuration), are described and the alpha-L-LNA oligomers are studied. Bicyclic 5-methylcytosin-1-yl and adenine-9-yl nucleoside derivatives have been prepared and the phosphoramidite approach has been used for the automated oligomerization leading to alpha-L-LNA oligomers. Binding studies revealed very efficient recognition of single-stranded DNA and RNA target oligonucleotide strands. Thus, stereoirregular alpha-L-LNA 11-mers containing a mixture of alpha-L-LNA monomers and DNA monomers ("mix-mer alpha-L-LNA") were shown to display DeltaT(m) values of +1 to +3 degrees C per modification toward DNA and +4 to +5 degrees C toward RNA when compared with the corresponding unmodified DNA x DNA and DNA x RNA reference duplexes. The corresponding DeltaT(m) values per modification for the stereoregular fully modified alpha-L-LNA were determined to be +4 degrees C (against DNA) and +5 degrees C (against RNA). 11-Mer alpha-L-LNAs (mix-mer alpha- L-LNA or fully modified alpha- L-LNA) were shown in vitro to be significantly stabilized toward 3'-exonucleolytic degradation. A duplex formed between RNA and either mix-mer alpha-L-LNA or fully modified alpha-L-LNA induced in vitro Escherichia coli RNase H-mediated cleavage, albeit very slow, of the RNA targets at high enzyme concentrations.</div></front></TEI><affiliations><list><country><li>Danemark</li></country></list><tree><noCountry><name sortKey="Bryld, Torsten" sort="Bryld, Torsten" uniqKey="Bryld T" first="Torsten" last="Bryld">Torsten Bryld</name><name sortKey="Gaubert, Gilles" sort="Gaubert, Gilles" uniqKey="Gaubert G" first="Gilles" last="Gaubert">Gilles Gaubert</name><name sortKey="H Kansson, Anders E" sort="H Kansson, Anders E" uniqKey="H Kansson A" first="Anders E" last="H Kansson">Anders E. H Kansson</name><name sortKey="Herdewijn, Piet" sort="Herdewijn, Piet" uniqKey="Herdewijn P" first="Piet" last="Herdewijn">Piet Herdewijn</name><name sortKey="Kvaern, Lisbet" sort="Kvaern, Lisbet" uniqKey="Kvaern L" first="Lisbet" last="Kvaern">Lisbet Kvaern</name><name sortKey="Verbeure, Birgit" sort="Verbeure, Birgit" uniqKey="Verbeure B" first="Birgit" last="Verbeure">Birgit Verbeure</name><name sortKey="Wengel, Jesper" sort="Wengel, Jesper" uniqKey="Wengel J" first="Jesper" last="Wengel">Jesper Wengel</name></noCountry><country name="Danemark"><noRegion><name sortKey="S Rensen, Mads D" sort="S Rensen, Mads D" uniqKey="S Rensen M" first="Mads D" last="S Rensen">Mads D. S Rensen</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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