Synthesis of nucleosides and dNTPs bearing oligopyridine ligands linked through an octadiyne tether, their incorporation into DNA and complexation with transition metal cations
Language English Country Great Britain, England Media print
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
23090069
DOI
10.1039/c2ob26881g
Knihovny.cz E-resources
- MeSH
- Alkynes chemistry MeSH
- DNA chemistry MeSH
- Cations chemistry MeSH
- Ligands MeSH
- Molecular Structure MeSH
- Nucleosides chemical synthesis chemistry MeSH
- Organometallic Compounds chemical synthesis chemistry MeSH
- Polyphosphates chemical synthesis chemistry MeSH
- Transition Elements chemistry MeSH
- Pyridines chemistry MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Alkynes MeSH
- DNA MeSH
- Cations MeSH
- Ligands MeSH
- Nucleosides MeSH
- Organometallic Compounds MeSH
- Polyphosphates MeSH
- Transition Elements MeSH
- Pyridines MeSH
- triphosphoric acid MeSH Browser
Modified nucleosides (dA(R)s and dC(R)s) bearing bipyridine or terpyridine ligands attached through an octadiyne linker were prepared by single-step aqueous-phase Sonogashira cross-coupling of 7-iodo-7-deaza-2'-deoxyadenosine and 5-iodo-2'-deoxycytidine with the corresponding bipyridine- or terpyridine-octadiynes and were triphosphorylated to the corresponding nucleoside triphosphates (dA(R)TPs and dC(R)TPs). The modified dN(R)TPs were successfully incorporated into the oligonucleotides by primer extension experiment (PEX) using different DNA polymerases and the PEX products were used for post-synthetic complexation with divalent metal cations. The complexation of these DNAs containing flexibly-tethered ligands was compared with the previously reported ones bearing rigid acetylene-linked ligands suggesting the possible formation of both inter- and intra-strand complexes with Ni(2+) or Fe(2+).
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