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Keywords:

  • alkenes;
  • bioorthogonal chemistry;
  • biotechnology;
  • cycloaddition;
  • tetrazoles
Thumbnail image of graphical abstract

Quick as a flash! A series of conformationally constrained, macrocyclic tetrazoles were expediently prepared by double alkylation of a bis(o-phenolyl)tetrazole precursor. Several of them showed excellent reactivity toward norbornene in a photoinduced tetrazole–alkene cycloaddition reaction in organic solvent, as well as toward a norbornene-modified protein in phosphate-buffered saline buffer (see scheme).