Specific and spatial labeling of choline-containing teichoic acids in Streptococcus pneumoniae by click chemistry

Chem Commun (Camb). 2017 Sep 21;53(76):10572-10575. doi: 10.1039/c7cc05646j.


Propargyl-choline was efficiently incorporated into teichoic acid (TA) polymers on the surface of Streptococcus pneumoniae. The introduction of a fluorophore by click chemistry enabled sufficient labeling of the pneumococcus, as well as its specific detection when mixed with other bacterial species. The labeling is localized at the septal site, suggesting a similar location of the TA and peptidoglycan (PG) synthetic machineries. This method is a unique opportunity to improve our understanding of the spatial location of pneumococcal TA biosynthesis.

MeSH terms

  • Alkynes / chemical synthesis
  • Alkynes / chemistry*
  • Choline / analogs & derivatives*
  • Choline / chemical synthesis
  • Choline / chemistry
  • Click Chemistry*
  • Fluorescence
  • Molecular Structure
  • Staining and Labeling*
  • Streptococcus pneumoniae / chemistry*
  • Streptococcus pneumoniae / cytology
  • Teichoic Acids / analysis*


  • Alkynes
  • Teichoic Acids
  • propargylcholine
  • Choline