N-Branched acyclic nucleoside phosphonates as monomers for the synthesis of modified oligonucleotides
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...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2015-04, Vol.13 (15), p.4449-4458 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Hocková, Dana Rosenbergová, Šárka Ménová, Petra Páv, Ondřej Pohl, Radek Novák, Pavel Rosenberg, Ivan |
| description | 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. |
| doi_str_mv | 10.1039/c4ob02265c |
| format | Article |
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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.</abstract><cop>England</cop><pmid>25766752</pmid><doi>10.1039/c4ob02265c</doi><tpages>10</tpages></addata></record> |
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| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Adenine - chemical synthesis Adenine - chemistry Base Sequence DNA-Directed DNA Polymerase - metabolism Humans Nucleic Acid Synthesis Inhibitors - chemical synthesis Nucleic Acid Synthesis Inhibitors - chemistry Nucleic Acid Synthesis Inhibitors - pharmacology Nucleosides - chemical synthesis Nucleosides - chemistry Nucleosides - pharmacology Oligonucleotides - chemical synthesis Oligonucleotides - chemistry Oligonucleotides - pharmacology Organophosphonates - chemical synthesis Organophosphonates - chemistry Organophosphonates - pharmacology Thymine - chemical synthesis Thymine - chemistry |
| title | N-Branched acyclic nucleoside phosphonates as monomers for the synthesis of modified oligonucleotides |
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