Combinatorial and automated synthesis of phosphodiester galactosyl cluster on solid support by click chemistry assisted by microwaves

J Org Chem. 2008 Aug 1;73(15):6014-7. doi: 10.1021/jo8009837. Epub 2008 Jul 4.

Abstract

Small libraries of di-, tri-, and tetragalactosyl clusters were efficiently synthesized using combinatorial methodology, on solid support, by click chemistry assisted by microwaves, starting from different poly alkyne DNA-based scaffolds and two galactosyl azide derivatives. The scaffold was synthesized by standard DNA solid-supported phosphoramidite chemistry using a novel alkyne phosphoramidite and an alkyne solid support. The proportion of each glycocluster in a library was modulated using different molar ratios of both galactose azides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylation
  • Azides / chemistry
  • Chromatography, High Pressure Liquid
  • Combinatorial Chemistry Techniques
  • Esters / chemistry*
  • Galactose / chemical synthesis*
  • Galactose / chemistry
  • Microwaves*
  • Molecular Structure
  • Phosphorus Compounds / chemical synthesis*
  • Phosphorus Compounds / chemistry
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Substances

  • Azides
  • Esters
  • Phosphorus Compounds
  • Galactose