Abstract
Bioincorporation of the methionine analogue S-(2-fluoroethyl)-l-homocysteine (l-MFE) into bacteriophage lysozyme overproduced in Escherichia coli results not only in the expected l-MFE incorporation but surprisingly substantial l-vinthionine incorporation into the labeled lysozymes. Synthetic l-vinthionine itself however is not activated by purified Escherichia coli methionyl-tRNA synthetase. The indirect preparation of vinthionine-containing proteins has the potential to be an alternate strategy to prepare vinyl thioether moieties for click chemistry applications on proteins.
MeSH terms
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Amino Acids / analysis
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Amino Acids / metabolism*
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Bacteriophage lambda / chemistry
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Bacteriophage lambda / metabolism*
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Escherichia coli / chemistry
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Escherichia coli / metabolism*
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Escherichia coli / virology*
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Escherichia coli Proteins / analysis
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Escherichia coli Proteins / metabolism
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Ethionine / analogs & derivatives
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Ethionine / analysis
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Ethionine / metabolism
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Halogenation
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Homocysteine / analogs & derivatives
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Homocysteine / analysis
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Homocysteine / metabolism
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Methionine / analogs & derivatives*
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Methionine / analysis
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Methionine / metabolism
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Methionine-tRNA Ligase / analysis
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Methionine-tRNA Ligase / metabolism
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Models, Molecular
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Muramidase / analysis
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Muramidase / metabolism*
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Protein Biosynthesis
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Viral Proteins / analysis
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Viral Proteins / metabolism*
Substances
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Amino Acids
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Escherichia coli Proteins
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Viral Proteins
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Homocysteine
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vinthionine
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Methionine
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Muramidase
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Methionine-tRNA Ligase
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Ethionine