1,2,4-Triazines Are Versatile Bioorthogonal Reagents

J Am Chem Soc. 2015 Jul 8;137(26):8388-91. doi: 10.1021/jacs.5b05100. Epub 2015 Jun 25.

Abstract

A new class of bioorthogonal reagents, 1,2,4-triazines, is described. These scaffolds are stable in biological media and capable of robust reactivity with trans-cyclooctene (TCO). The enhanced stability of the triazine scaffold enabled its direct use in recombinant protein production. The triazine-TCO reaction can also be used in tandem with other bioorthogonal cycloaddition reactions. These features fill current voids in the bioorthogonal toolkit.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Chemistry, Organic / methods
  • Codon
  • Cycloaddition Reaction
  • Cyclooctanes / chemistry
  • Cysteine / chemistry
  • Green Fluorescent Proteins / chemistry
  • Hydrolysis
  • Indicators and Reagents / chemistry*
  • Methanocaldococcus / enzymology
  • Models, Chemical
  • Recombinant Proteins / chemistry
  • Triazines / chemistry*
  • Tyrosine-tRNA Ligase / chemistry

Substances

  • Codon
  • Cyclooctanes
  • Indicators and Reagents
  • Recombinant Proteins
  • Triazines
  • Green Fluorescent Proteins
  • 1,2,4-triazine
  • Tyrosine-tRNA Ligase
  • Cysteine