Synthesis and properties of oligonucleotides containing C8-deoxyguanosine arylamine adducts of borderline carcinogens

J Org Chem. 2006 Dec 22;71(26):9728-38. doi: 10.1021/jo061803t.

Abstract

C8-Arylamine-dG adducts of borderline carcinogens and the bladder and breast carcinogen 4-aminobiphenyl were prepared using cross-coupling chemistry. These adducts were converted into the corresponding C8-arylamine-5'-O-DMTr-2'-deoxyguanosine phosphoramidites and then used as building blocks for automated synthesis of site-specifically modified oligonucleotides. The oligonucleotides were characterized by UV melting temperature analysis, enzymatic digestion, and circular dichroism.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Carcinogens / chemistry*
  • Deoxyguanosine / analogs & derivatives*
  • Deoxyguanosine / chemistry
  • Molecular Structure
  • Oligonucleotides / chemical synthesis*
  • Oligonucleotides / chemistry*
  • Stereoisomerism

Substances

  • Amines
  • Carcinogens
  • Oligonucleotides
  • Deoxyguanosine