Synthesis of nucleoside mono- and triphosphates bearing oligopyridine ligands, their incorporation into DNA and complexation with transition metals

Org Biomol Chem. 2012 Jan 7;10(1):49-55. doi: 10.1039/c1ob06359f. Epub 2011 Nov 9.

Abstract

Modified nucleoside mono- (dA(R)MPs and dC(R)MPs) and triphosphates (dA(R)TPs and dC(R)TPs) bearing bipyridine or terpyridine ligands attached via acetylene linker were prepared by single-step aqueous-phase Sonogashira cross-coupling of 7-iodo-7-deaza-dAMP or -dATP, and 5-iodo-dCMP or -dCTP with the corresponding bipyridine- or terpyridine-linked acetylenes. 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 Fe(2+).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Base Sequence
  • DNA / chemistry*
  • DNA Primers
  • Ligands
  • Magnetic Resonance Spectroscopy
  • Phosphates / chemistry*
  • Pyridines / chemistry*
  • Transition Elements / chemistry*

Substances

  • DNA Primers
  • Ligands
  • Phosphates
  • Pyridines
  • Transition Elements
  • DNA
  • pyridine