Synthesis of nucleosides and dNTPs bearing oligopyridine ligands linked through an octadiyne tether, their incorporation into DNA and complexation with transition metal cations

0391779 - ÚOCHB 2014 RIV GB eng J - Journal Article
Kalachová, Lubica - Pohl, Radek - Bednárová, Lucie - Fanfrlík, Jindřich - Hocek, Michal
Synthesis of nucleosides and dNTPs bearing oligopyridine ligands linked through an octadiyne tether, their incorporation into DNA and complexation with transition metal cations.
Organic & Biomolecular Chemistry. Roč. 11, č. 1 (2013), s. 78-89. ISSN 1477-0520. E-ISSN 1477-0539
R&D Projects: GA ČR GA203/09/0317
Institutional support: RVO:61388963
Keywords : cross-coupling reactions * base-pair * solid-phase synthesis * polymerase incorporation
Subject RIV: CC - Organic Chemistry
Impact factor: 3.487, year: 2013

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 Ni2+ or Fe2+.
Permanent Link: http://hdl.handle.net/11104/0220752