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Keywords:

  • charge transport;
  • DNA;
  • hole traps;
  • nucleosides;
  • oxidation

Abstract

DNA duplexes containing 8-cyclopropyl-2′-deoxyguanosine (8CPG) were synthesized to investigate the effect of the C8-modified deoxyguanosine as a kinetic trap for transient hole occupancy on guanines during DNA-mediated hole transport (HT). Thermal denaturation and CD spectra show that DNA duplexes containing 8CPG are able to form stable B-form duplexes. Photoirradiation of terminal tethered anthraquinone can induce oxidative decomposition of 8CPG through DNA HT along adenine tracts with lengths of up to 4.8 nm. Shallow and periodic distance dependence was observed in a long adenine tract with intervening guanines. The efficient charge transport indicates that 8CPG can electronically couple well with a DNA bridge and form HT-active conformational domains to facilitate transient hole delocalization over an adenine tract.