title: Genetically encoded unstrained olefins for live cell labeling with tetrazine dyes.
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.
authors.affiliation: Department of Chemistry, Texas A&M University, College Station, TX 77843, USA. wliu@chem.tamu.edu.
authors.forename: Yan-Jiun
authors.initials: YJ
authors.lastname: Lee
authors.forename: Yadagiri
authors.initials: Y
authors.lastname: Kurra
authors.forename: Yanyan
authors.initials: Y
authors.lastname: Yang
authors.forename: Jessica
authors.initials: J
authors.lastname: Torres-Kolbus
authors.forename: Alexander
authors.initials: A
authors.lastname: Deiters
authors.forename: Wenshe R
authors.initials: WR
authors.lastname: Liu
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000596:Amino Acids / Q000378:metabolism; D000604:Amino Acyl-tRNA Synthetases / Q000235:genetics / Q000378:metabolism; D001425:Bacterial Outer Membrane Proteins / Q000737:chemistry / Q000378:metabolism; D061565:Cycloaddition Reaction; D004926:Escherichia coli / Q000378:metabolism; D029968:Escherichia coli Proteins / Q000737:chemistry / Q000378:metabolism; D019793:Fluorescein / Q000737:chemistry; D005456:Fluorescent Dyes / Q000737:chemistry*; D049452:Green Fluorescent Proteins / Q000737:chemistry; D006573:Heterocyclic Compounds, 1-Ring / Q000737:chemistry*; D006867:Hydrolases / Q000737:chemistry / Q000378:metabolism; D009154:Mutation; D012343:RNA, Transfer / Q000378:metabolism
chemical_list: D000475:Alkenes; D000596:Amino Acids; D001425:Bacterial Outer Membrane Proteins; D029968:Escherichia coli Proteins; D005456:Fluorescent Dyes; D006573:Heterocyclic Compounds, 1-Ring; C000598289:tetrazine dye 10; C482905:OmpX protein, E coli; D049452:Green Fluorescent Proteins; D012343:RNA, Transfer; D006867:Hydrolases; D000604:Amino Acyl-tRNA Synthetases; D019793:Fluorescein