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
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Alkenes / chemistry*
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Amino Acids / metabolism
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Amino Acyl-tRNA Synthetases / genetics
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Amino Acyl-tRNA Synthetases / metabolism
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Bacterial Outer Membrane Proteins / chemistry
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Bacterial Outer Membrane Proteins / metabolism
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Cycloaddition Reaction
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Escherichia coli / metabolism
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Escherichia coli Proteins / chemistry
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Escherichia coli Proteins / metabolism
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Fluorescein / chemistry
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Fluorescent Dyes / chemistry*
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Green Fluorescent Proteins / chemistry
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Heterocyclic Compounds, 1-Ring / chemistry*
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Hydrolases / chemistry
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Hydrolases / metabolism
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Mutation
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RNA, Transfer / metabolism
Substances
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Alkenes
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Amino Acids
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Bacterial Outer Membrane Proteins
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Escherichia coli Proteins
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Fluorescent Dyes
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Heterocyclic Compounds, 1-Ring
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tetrazine dye 10
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OmpX protein, E coli
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Green Fluorescent Proteins
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RNA, Transfer
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Hydrolases
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Amino Acyl-tRNA Synthetases
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Fluorescein