The synthesis of diene-containing nucleoside phosphoramidites and their use in the labeling of oligonucleotides

Nucleosides Nucleotides Nucleic Acids. 2005;24(5-7):761-5. doi: 10.1081/ncn-200060085.

Abstract

A variety of furan-modified nucleoside phosphoramidite monomers has been prepared and efficiently incorporated into oligonucleotides. These take part in Diels-Alder reactions with fluorescent maleimides to give fluorescent-labeled oligonucleotides. This represents a strategy for oligonucleotide labeling that is orthogonal to amine-based methods.

MeSH terms

  • Amines / chemistry
  • Deoxycytidine / chemistry
  • Fluorescent Dyes / pharmacology
  • Furans / chemistry
  • Hydrogen-Ion Concentration
  • Macromolecular Substances
  • Models, Chemical
  • Molecular Biology / methods*
  • Nucleosides / chemistry*
  • Nucleotides / chemistry
  • Oligodeoxyribonucleotides / chemistry
  • Oligonucleotides / chemistry*
  • Organophosphorus Compounds / chemistry*
  • Temperature

Substances

  • Amines
  • Fluorescent Dyes
  • Furans
  • Macromolecular Substances
  • Nucleosides
  • Nucleotides
  • Oligodeoxyribonucleotides
  • Oligonucleotides
  • Organophosphorus Compounds
  • phosphoramidite
  • Deoxycytidine
  • furan