Bifacial nucleoside as a surrogate for both T and A in duplex DNA

J Am Chem Soc. 2011 May 11;133(18):6926-9. doi: 10.1021/ja201397e. Epub 2011 Apr 15.

Abstract

A new functional bifacial nucleoside derived from 7-aminopyrimido[4,5-d]pyrimidine-2,4(1H,3H)-dione, a Janus-type nucleobase, has been synthesized and incorporated into DNA oligonucleotides. The nucleobase, having self-complementary H-bonding faces, mimics both T and A and engages in the corresponding Watson-Crick-like base pairs, forming stable duplexes.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Adenosine / chemistry*
  • Base Pairing*
  • DNA / chemistry*
  • Hydrogen Bonding
  • Molecular Mimicry*
  • Nucleosides / chemical synthesis
  • Nucleosides / chemistry*
  • Oligodeoxyribonucleotides / chemistry
  • Pyrimidinones / chemistry*
  • Thermodynamics
  • Thymidine / chemistry*

Substances

  • 7-aminopyrimido(4,5-d)pyrimidine-2,4(1H,3H)-dione
  • Nucleosides
  • Oligodeoxyribonucleotides
  • Pyrimidinones
  • DNA
  • Adenosine
  • Thymidine