A remarkable stabilization of complexes formed by 2,6-diaminopurine oligonucleotide N3'-->P5' phophoramidates

Nucleosides Nucleotides Nucleic Acids. 2000 Oct-Dec;19(10-12):1553-67. doi: 10.1080/15257770008045446.

Abstract

2'-Deoxyribo- and ribo-oligonucleotide N3'-->P5'phosphoramidates containing 2,6-diaminopurine nucleosides were synthesized. Thermal denaturation experiments demonstrated a significant stabilization of the complexes formed by these compounds with DNA and RNA complementary strands, relative to adenosine-containing phosphoramidate counterparts. The increase in melting temperature of the complexes reached up to 6.9 degrees C per substitution. The observed stabilization was attributed to the apparent synergistic effects of N-type sugar puckering of the oligonucleotide N3'-->P5' phosphoramidate backbone, and the ability of 2,6-diaminopurine bases to form three hydrogen bonds.

MeSH terms

  • 2-Aminopurine / analogs & derivatives*
  • 2-Aminopurine / chemistry*
  • Magnetic Resonance Spectroscopy
  • Organophosphorus Compounds / chemistry*
  • Thionucleotides / chemistry*

Substances

  • Organophosphorus Compounds
  • Thionucleotides
  • 2-Aminopurine
  • 2,6-diaminopurine