Bioorthogonal labelling of living bacteria using unnatural amino acids containing nitrones and a nitrone derivative of vancomycin

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DOIResolve DOI: http://doi.org/10.1039/c5cc04901f
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TypeArticle
Journal titleChemical Communications
ISSN1359-7345
Volume51
Issue62
Pages1250112504; # of pages: 4
Subjectcarboxylic acid; dextro amino acid; dimethyl sulfoxide; macrogol; nitrone derivative; vancomycin; bacterial cell wall; cycloaddition; Escherichia coli; fluorescence microscopy; Gram bacterium; Lactococcus lactis; Listeria innocua; protein structure
AbstractUnnatural 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.
Publication date
LanguageEnglish
AffiliationMedical Devices; National Research Council Canada
Peer reviewedYes
NPARC number21276975
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Record identifier2fa82a67-711e-4927-bf2c-52e6a835fcdd
Record created2015-11-10
Record modified2016-05-09
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