A-hydroxyphosphonate oligonucleotides: a promising DNA type?
Identifieur interne : 000238 ( Ncbi/Curation ); précédent : 000237; suivant : 000239A-hydroxyphosphonate oligonucleotides: a promising DNA type?
Auteurs : Sárka Králíková [République tchèque] ; Milos Budesínsk ; Ivan RosenbergSource :
- Nucleosides, nucleotides & nucleic acids [ 1525-7770 ]
Descripteurs français
- KwdFr :
- MESH :
- analogues et dérivés : Thymidine.
- synthèse chimique : Oligodésoxyribonucléotides.
- ADN, Conformation d'acide nucléique, Indicateurs et réactifs, Oligodésoxyribonucléotides, Phosphonates, Structure moléculaire.
English descriptors
- KwdEn :
- MESH :
- chemical , analogs & derivatives : Thymidine.
- chemical , chemical synthesis : Oligodeoxyribonucleotides.
- chemical , chemistry : DNA, Oligodeoxyribonucleotides.
- chemical : Indicators and Reagents, Organophosphonates.
- Molecular Structure, Nucleic Acid Conformation.
Abstract
The synthesis of monomers (S)-1, (R)-1 and 2 derived from (5'S)-, (5'R)-2'-deoxythymidine-5'-C-phosphonic acids and 2',5'-dideoxythymidine-5'-C-phosphonic acids was elaborated. The protection of the 5'-hydroxyl by the methoxycarbonyl group was a key step of the synthesis. Prepared monomers were used for the solid-phase assembly of several types oligothymidylate 15-mers (S)-3, (S)-4, (S)-5, (R)-4 and (R)-5 containing the chiral 3'-O-P-CH(OH)-5'' internucleotide linkage. Their hybridization properties with dA15 and rA15 were studied as well as their resistance against nuclease cleavage.
DOI: 10.1081/NCN-120022736
PubMed: 14565344
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pubmed:14565344Le document en format XML
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<author><name sortKey="Budesinsk, Milos" sort="Budesinsk, Milos" uniqKey="Budesinsk M" first="Milos" last="Budesínsk">Milos Budesínsk</name>
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<author><name sortKey="Budesinsk, Milos" sort="Budesinsk, Milos" uniqKey="Budesinsk M" first="Milos" last="Budesínsk">Milos Budesínsk</name>
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<term>Oligodeoxyribonucleotides (chemical synthesis)</term>
<term>Oligodeoxyribonucleotides (chemistry)</term>
<term>Organophosphonates</term>
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<term>Conformation d'acide nucléique</term>
<term>Indicateurs et réactifs</term>
<term>Oligodésoxyribonucléotides ()</term>
<term>Oligodésoxyribonucléotides (synthèse chimique)</term>
<term>Phosphonates</term>
<term>Structure moléculaire</term>
<term>Thymidine (analogues et dérivés)</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>DNA</term>
<term>Oligodeoxyribonucleotides</term>
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<keywords scheme="MESH" type="chemical" xml:lang="en"><term>Indicators and Reagents</term>
<term>Organophosphonates</term>
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<term>Conformation d'acide nucléique</term>
<term>Indicateurs et réactifs</term>
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<front><div type="abstract" xml:lang="en">The synthesis of monomers (S)-1, (R)-1 and 2 derived from (5'S)-, (5'R)-2'-deoxythymidine-5'-C-phosphonic acids and 2',5'-dideoxythymidine-5'-C-phosphonic acids was elaborated. The protection of the 5'-hydroxyl by the methoxycarbonyl group was a key step of the synthesis. Prepared monomers were used for the solid-phase assembly of several types oligothymidylate 15-mers (S)-3, (S)-4, (S)-5, (R)-4 and (R)-5 containing the chiral 3'-O-P-CH(OH)-5'' internucleotide linkage. Their hybridization properties with dA15 and rA15 were studied as well as their resistance against nuclease cleavage.</div>
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