Synthesis and evaluation of oligodeoxynucleotides containing acyclic nucleosides: introduction of three novel analogues and a summary

Bioorg Med Chem. 1995 Jan;3(1):19-28. doi: 10.1016/0968-0896(94)00143-q.

Abstract

Novel flexible oligodeoxynucleotides containing (S)-1-(2,3-dihydroxypropyl)thymine or 2',3'-seco-thymidine nucleoside analogues were synthesized on an automated DNA-synthesizer. Oligodeoxynucleotides with one, two or three acyclic nucleosides incorporated in the middle or in the ends of 17-mers have been evaluated. 3'-End-modified oligomers were significantly stabilized towards 3'-exonucleolytic degradation compared to unmodified analogues and showed acceptable hybridization properties as measured by UV experiments. For oligodeoxynucleotide analogues containing the three novel acyclic monomers in the middle, a more pronounced reduction in duplex stability was observed. All oligodeoxynucleotides containing acyclic nucleoside analogues made so far are evaluated with respect to stability towards 3'-exonucleolytic degradation and hybridization properties.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Base Sequence
  • Exonucleases / metabolism
  • Molecular Sequence Data
  • Molecular Structure
  • Nucleic Acid Denaturation
  • Nucleic Acid Hybridization
  • Nucleosides / chemical synthesis*
  • Oligodeoxyribonucleotides / chemical synthesis*
  • Oligodeoxyribonucleotides / chemistry
  • Oligodeoxyribonucleotides / metabolism

Substances

  • Nucleosides
  • Oligodeoxyribonucleotides
  • Exonucleases