Oligonucleotides containing 7-vinyl-7-deazaguanine as a facile strategy for expanding the functional diversity of DNA

Bioorg Med Chem Lett. 2002 Aug 5;12(15):1895-6. doi: 10.1016/s0960-894x(02)00334-7.

Abstract

A modified nucleobase 7-vinyl-7-deazaguanine ((V)G) produced adducts with maleimides through Diels-Alder cycloaddition under very mild conditions. By this method, post-synthetic modification to oligonucleotides with diverse functionality (carboxylic acid, pyrene, benzophenone, succinimidyl ester, nitroxide and biotin) was accomplished.

MeSH terms

  • Base Sequence
  • DNA / chemistry*
  • Guanine / analogs & derivatives*
  • Guanine / chemistry*
  • Maleimides / chemistry
  • Oligonucleotides / chemical synthesis*

Substances

  • 7-vinyl-7-deazaguanine
  • Maleimides
  • Oligonucleotides
  • Guanine
  • DNA