title: Intriguing cellular processing of a fluorinated amino acid during protein biosynthesis in Escherichia coli.
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.
authors.affiliation: Department of Chemistry, University of Waterloo, 200 University Avenue West, Waterloo, ON N2L 3G1 Canada. jhonek@uwaterloo.ca.
authors.forename: Mark D
authors.initials: MD
authors.lastname: Vaughan
authors.affiliation: Department of Chemistry, University of Waterloo, 200 University Avenue West, Waterloo, ON N2L 3G1 Canada. jhonek@uwaterloo.ca.
authors.forename: Zhengding
authors.initials: Z
authors.lastname: Su
authors.affiliation: Department of Chemistry, University of Waterloo, 200 University Avenue West, Waterloo, ON N2L 3G1 Canada. jhonek@uwaterloo.ca.
authors.forename: Elisabeth
authors.initials: E
authors.lastname: Daub
authors.affiliation: Department of Chemistry, University of Waterloo, 200 University Avenue West, Waterloo, ON N2L 3G1 Canada. jhonek@uwaterloo.ca.
authors.forename: J F
authors.identifier: http://orcid.org/0000-0002-4035-4538
authors.initials: JF
authors.lastname: Honek
mesh_terms: D000596:Amino Acids / Q000032:analysis / Q000378:metabolism*; D010582:Bacteriophage lambda / Q000737:chemistry / Q000378:metabolism*; D004926:Escherichia coli / Q000737:chemistry / Q000378:metabolism* / Q000821:virology*; D029968:Escherichia coli Proteins / Q000032:analysis / Q000378:metabolism; D005001:Ethionine / Q000031:analogs & derivatives / Q000032:analysis / Q000378:metabolism; D054879:Halogenation; D006710:Homocysteine / Q000031:analogs & derivatives / Q000032:analysis / Q000378:metabolism; D008715:Methionine / Q000031:analogs & derivatives* / Q000032:analysis / Q000378:metabolism; D008718:Methionine-tRNA Ligase / Q000032:analysis / Q000378:metabolism; D008958:Models, Molecular; D009113:Muramidase / Q000032:analysis / Q000378:metabolism*; D014176:Protein Biosynthesis; D014764:Viral Proteins / Q000032:analysis / Q000378:metabolism*
chemical_list: D000596:Amino Acids; D029968:Escherichia coli Proteins; D014764:Viral Proteins; D006710:Homocysteine; C020543:vinthionine; D008715:Methionine; D009113:Muramidase; D008718:Methionine-tRNA Ligase; D005001:Ethionine