N-Branched acyclic nucleoside phosphonates as monomers for the synthesis of modified oligonucleotides
Jazyk angličtina Země Anglie, Velká Británie Médium print
Typ dokumentu časopisecké články, práce podpořená grantem
PubMed
25766752
DOI
10.1039/c4ob02265c
Knihovny.cz E-zdroje
- MeSH
- adenin chemická syntéza chemie MeSH
- DNA-dependentní DNA-polymerasy metabolismus MeSH
- inhibitory syntézy nukleových kyselin chemická syntéza chemie farmakologie MeSH
- lidé MeSH
- nukleosidy chemická syntéza chemie farmakologie MeSH
- oligonukleotidy chemická syntéza chemie farmakologie MeSH
- organofosfonáty chemická syntéza chemie farmakologie MeSH
- sekvence nukleotidů MeSH
- thymin chemická syntéza chemie MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- adenin MeSH
- DNA-dependentní DNA-polymerasy MeSH
- inhibitory syntézy nukleových kyselin MeSH
- nukleosidy MeSH
- oligonukleotidy MeSH
- organofosfonáty MeSH
- thymin 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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