Metabolic glycan imaging by isonitrile-tetrazine click chemistry

Chembiochem. 2013 Jun 17;14(9):1063-7. doi: 10.1002/cbic.201300130. Epub 2013 May 13.

Abstract

Seeing the sugar coating: N-Acetyl-glucosamine and mannosamine derivatives tagged with an isonitrile group are metabolically incorporated into cell-surface glycans and can be detected with a fluorescent tetrazine. This bioorthogonal isonitrile-tetrazine ligation is also orthogonal to the commonly used azide-cyclooctyne ligation, and so will allow simultaneous detection of the incorporation of two different sugars.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylglucosamine / chemistry
  • Animals
  • Biotin / chemistry
  • Cell Line, Tumor
  • Click Chemistry
  • Fluorescent Dyes / chemistry
  • Hexosamines / chemistry
  • Mice
  • Microscopy, Confocal
  • Nitriles / chemistry*
  • Polysaccharides / chemistry*
  • Tetrazoles / chemistry*

Substances

  • Fluorescent Dyes
  • Hexosamines
  • Nitriles
  • Polysaccharides
  • Tetrazoles
  • mannosamine
  • Biotin
  • Acetylglucosamine