Difluoro-C4'-oxidized abasic site for efficient amine modification in biological systems

Org Lett. 2012 Dec 7;14(23):5852-5. doi: 10.1021/ol302703m. Epub 2012 Nov 14.

Abstract

An oligodeoxynucleotide (ODN) containing a 2',2'-difluorinated analogue of a C4'-oxidized abasic site (C4'-OAS) was designed for the amine modification of biomolecules that interact with nucleic acids. In contrast to the parent C4'-OAS, which yielded amine-modified products accompanied by DNA strand scission, the ODN containing the difluoro C4'-OAS efficiently yielded products carrying ODNs. The amine modification proceeded without additional reagents being required and might be applicable to reactions in biological systems.

MeSH terms

  • Amines / chemistry*
  • DNA / chemistry
  • DNA Damage
  • Hydrocarbons, Fluorinated / chemical synthesis*
  • Hydrocarbons, Fluorinated / chemistry
  • Hydrocarbons, Fluorinated / radiation effects
  • Molecular Structure
  • Oligodeoxyribonucleotides / chemical synthesis*
  • Oligodeoxyribonucleotides / chemistry
  • Oligodeoxyribonucleotides / radiation effects
  • Oxidation-Reduction

Substances

  • Amines
  • Hydrocarbons, Fluorinated
  • Oligodeoxyribonucleotides
  • DNA