N-Branched acyclic nucleoside phosphonates as monomers for the synthesis of modified oligonucleotides
Language English Country England, Great Britain Media print
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
25766752
DOI
10.1039/c4ob02265c
Knihovny.cz E-resources
- MeSH
- Adenine chemical synthesis chemistry MeSH
- DNA-Directed DNA Polymerase metabolism MeSH
- Nucleic Acid Synthesis Inhibitors chemical synthesis chemistry pharmacology MeSH
- Humans MeSH
- Nucleosides chemical synthesis chemistry pharmacology MeSH
- Oligonucleotides chemical synthesis chemistry pharmacology MeSH
- Organophosphonates chemical synthesis chemistry pharmacology MeSH
- Base Sequence MeSH
- Thymine chemical synthesis chemistry MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Adenine MeSH
- DNA-Directed DNA Polymerase MeSH
- Nucleic Acid Synthesis Inhibitors MeSH
- Nucleosides MeSH
- Oligonucleotides MeSH
- Organophosphonates MeSH
- Thymine MeSH
Protected N-branched nucleoside phosphonates containing adenine and thymine bases were prepared as the monomers for the introduction of aza-acyclic nucleotide units into modified oligonucleotides. The phosphotriester and phosphoramidite methods were used for the incorporation of modified and natural units, respectively. The solid phase synthesis of a series of nonamers containing one central modified unit was successfully performed in both 3'→5' and 5'→3' directions. Hybridization properties of the prepared oligoribonucleotides and oligodeoxyribonucleotides were evaluated. The measurement of thermal characteristics of the complexes of modified nonamers with the complementary strand revealed a considerable destabilizing effect of the introduced units. We also examined the substrate/inhibitory properties of aza-acyclic nucleoside phosphono-diphosphate derivatives (analogues of nucleoside triphosphates) but neither inhibition of human and bacterial DNA polymerases nor polymerase-mediated incorporation of these triphosphate analogues into short DNA was observed.
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