Bioorthogonal labelling of living bacteria using unnatural amino acids containing nitrones and a nitrone derivative
Douglas A MacKenzie1, Allison R Sherratt, Mariya Chigrinova
1Life Sciences Division, National Research Council of Canada, Ottawa, ON K1A 0R6, Canada. John.Pezacki@nrc-cnrc.gc.ca.
Chemical Communications (Cambridge, England)
|July 8, 2015
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.
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