Genetically encoded unstrained olefins for live cell labeling with tetrazine dyes

Chem Commun (Camb). 2014 Nov 7;50(86):13085-8. doi: 10.1039/c4cc06435f.

Abstract

A number of non-canonical amino acids (NCAAs) with unstrained olefins are genetically encoded using mutant pyrrolysyl-tRNA synthetase-tRNA(Pyl)(CUA) pairs. These NCAAs readily undergo inverse electron-demand Diels-Alder cycloadditions with tetrazine dyes, leading to selective labeling of proteins bearing these NCAAs in live cells.

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

  • Alkenes / chemistry*
  • Amino Acids / metabolism
  • Amino Acyl-tRNA Synthetases / genetics
  • Amino Acyl-tRNA Synthetases / metabolism
  • Bacterial Outer Membrane Proteins / chemistry
  • Bacterial Outer Membrane Proteins / metabolism
  • Cycloaddition Reaction
  • Escherichia coli / metabolism
  • Escherichia coli Proteins / chemistry
  • Escherichia coli Proteins / metabolism
  • Fluorescein / chemistry
  • Fluorescent Dyes / chemistry*
  • Green Fluorescent Proteins / chemistry
  • Heterocyclic Compounds, 1-Ring / chemistry*
  • Hydrolases / chemistry
  • Hydrolases / metabolism
  • Mutation
  • RNA, Transfer / metabolism

Substances

  • Alkenes
  • Amino Acids
  • Bacterial Outer Membrane Proteins
  • Escherichia coli Proteins
  • Fluorescent Dyes
  • Heterocyclic Compounds, 1-Ring
  • tetrazine dye 10
  • OmpX protein, E coli
  • Green Fluorescent Proteins
  • RNA, Transfer
  • Hydrolases
  • Amino Acyl-tRNA Synthetases
  • Fluorescein