title: Bioorthogonal labelling of living bacteria using unnatural amino acids containing nitrones and a nitrone derivative of vancomycin.
abstract: Unnatural D-amino acids bearing endocyclic nitrones were developed for live-cell labelling of the bacterial peptidoglycan layer. Metabolic incorporation of D-Lys and D-Ala derivatives bearing different endocyclic nitrones was observed in E. coli, L. innocua, and L. lactis. The incorporated nitrones of these bacteria then rapidly underwent strain-promoted alkyne-nitrone cycloaddition (SPANC) reactions affording chemically modified bacteria.
authors.affiliation: Life Sciences Division, National Research Council of Canada, Ottawa, ON K1A 0R6, Canada. John.Pezacki@nrc-cnrc.gc.ca.
authors.forename: Douglas A
authors.initials: DA
authors.lastname: MacKenzie
authors.forename: Allison R
authors.initials: AR
authors.lastname: Sherratt
authors.forename: Mariya
authors.initials: M
authors.lastname: Chigrinova
authors.forename: Arnold J
authors.initials: AJ
authors.lastname: Kell
authors.forename: John Paul
authors.initials: JP
authors.lastname: Pezacki
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000737:chemistry*; D004926:Escherichia coli; D008087:Listeria; D009589:Nitrogen Oxides / Q000737:chemistry*; D010457:Peptidoglycan / Q000737:chemistry*; D014640:Vancomycin / Q000031:analogs & derivatives / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D000900:Anti-Bacterial Agents; D009589:Nitrogen Oxides; D010457:Peptidoglycan; C015388:nitrones; D014640:Vancomycin