Genetically encoded cyclopropene directs rapid, photoclick-chemistry-mediated protein labeling in mammalian cells

Angew Chem Int Ed Engl. 2012 Oct 15;51(42):10600-4. doi: 10.1002/anie.201205352. Epub 2012 Sep 20.

Abstract

We just click: Genetic incorporation of a cyclopropene amino acid CpK (see scheme) site-specifically into proteins in E. coli and mammalian cells was achieved using an orthogonal aminoacyl-tRNA synthetase/tRNA(CUA) pair (CpKRS/MbtRNA(CUA)). Cyclopropene exhibited fast reaction kinetics in the photoclick reaction and allowed rapid (ca. 2 min) labeling of proteins.

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

  • Amino Acid Sequence
  • Amino Acids / chemistry
  • Amino Acids / genetics
  • Amino Acyl-tRNA Synthetases / chemistry
  • Amino Acyl-tRNA Synthetases / genetics
  • Animals
  • Archaeal Proteins / chemistry
  • Archaeal Proteins / genetics
  • Click Chemistry / methods*
  • Cyclopropanes / chemistry*
  • Humans
  • Lysine / analogs & derivatives
  • Lysine / chemistry
  • Lysine / genetics
  • Mammals
  • Methanosarcina barkeri / enzymology
  • Methanosarcina barkeri / genetics
  • Molecular Sequence Data
  • RNA, Transfer, Amino Acid-Specific / chemistry
  • RNA, Transfer, Amino Acid-Specific / genetics

Substances

  • Amino Acids
  • Archaeal Proteins
  • Cyclopropanes
  • RNA, Transfer, Amino Acid-Specific
  • cyclopropene
  • Amino Acyl-tRNA Synthetases
  • pyrrolysine
  • Lysine