Surprising duplex stabilisation upon mismatch introduction within triply modified duplexes

Bioorg Chem. 2010 Jun;38(3):92-7. doi: 10.1016/j.bioorg.2010.01.002. Epub 2010 Jan 18.

Abstract

Three different modified phosphoramidite nucleoside building blocks equipped with additional protected imidazole, masked alcohol and masked carboxylate functionality are synthesized and incorporated into oligonucleotides. Based on the serine-protease active site model, doubly and triply modified duplexes are created and tested for stability. Analysis of different spatial distributions of the extra functionalities shows that careful positioning can even overcome duplex destabilisation caused by the introduction of mismatches.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Base Pair Mismatch
  • Base Sequence
  • Catalytic Domain
  • DNA / chemistry*
  • DNA, Catalytic / chemistry
  • Imidazoles / chemistry
  • Models, Molecular
  • Nucleic Acid Conformation
  • Nucleosides / chemistry
  • Oligonucleotides / chemical synthesis
  • Oligonucleotides / chemistry*
  • Organophosphorus Compounds / chemistry
  • Serine Proteases / chemistry

Substances

  • DNA, Catalytic
  • Imidazoles
  • Nucleosides
  • Oligonucleotides
  • Organophosphorus Compounds
  • phosphoramidite
  • DNA
  • Serine Proteases