Incorporation of 2'-deoxy-6-thioguanosine into G-rich oligodeoxyribonucleotides inhibits G-tetrad formation and facilitates triplex formation

Biochemistry. 1995 Jan 24;34(3):765-72. doi: 10.1021/bi00003a009.

Abstract

An efficient and expeditious method for the synthesis of S6-(cyanoethyl)-N2-isobutyryl (or trifluoroacetyl)-2'-deoxy-6-thioguanosine (7 and 2) from 2'-deoxyguanosine (G) has been developed. Compound 7 has been incorporated into several G-rich triple-helix-forming oligonucleotides (TFOs) using solid-support, phosphoramidite chemistry. The purified oligonucleotides containing 2'-deoxy-6-thioguanosine (S6-dG) residues in the place of G have been characterized by nucleoside composition analysis. These modified TFOs have been shown to be stable in aqueous, as well as buffered, solutions normally used to assay triple-helix formation. It has also been demonstrated that partial incorporation of S6-dG is effective in inhibiting the formation of G tetrads in G-rich oligodeoxyribonucleotides, thus facilitating triple-helix formation in potassium-containing buffers.

MeSH terms

  • Base Sequence
  • Deoxyguanosine / analogs & derivatives*
  • Deoxyguanosine / chemistry
  • Hydrogen Bonding
  • Molecular Sequence Data
  • Nucleic Acid Conformation*
  • Oligodeoxyribonucleotides / chemistry*
  • Structure-Activity Relationship
  • Thionucleosides / chemistry*

Substances

  • Oligodeoxyribonucleotides
  • Thionucleosides
  • beta-2'-deoxythioguanosine
  • Deoxyguanosine