Synthesis of mannose and galactose oligonucleotide conjugates by bi-click chemistry

J Org Chem. 2009 Feb 6;74(3):1218-22. doi: 10.1021/jo802536q.

Abstract

Glyco oligonucleotide conjugates, each exhibiting two mannose and two galactose residues, were efficiently synthesized by two successive 1,3-dipolar cycloadditions (click chemistry). Two phosphoramidite derivatives were used: one bearing a bromoalkyl group as a precursor to azide functionalization and another bearing a propargyl group. After a first cycloaddition with a mannosyl-azide derivative, the bromine atoms were substituted with NaN(3) and a second click reaction was performed with a 1'-O-propargyl galactose, affording the heteroglyco oligonucleotide conjugate.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid
  • DNA / chemical synthesis
  • DNA / chemistry
  • Galactose / analogs & derivatives*
  • Galactose / chemistry
  • Mannose / analogs & derivatives*
  • Mannose / chemistry
  • Oligonucleotides / chemical synthesis*
  • Oligonucleotides / chemistry
  • Organophosphorus Compounds / chemical synthesis
  • Organophosphorus Compounds / chemistry
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Substances

  • Oligonucleotides
  • Organophosphorus Compounds
  • phosphoramidite
  • DNA
  • Mannose
  • Galactose