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ACS Chem Biol. 2013 Mar 15;8(3):500-5. doi: 10.1021/cb3004995. Epub 2013 Jan 11.

(D)-Amino acid chemical reporters reveal peptidoglycan dynamics of an intracellular pathogen.

Author information

1
Department of Chemistry, University of California, Berkeley, CA 94720, USA.

Abstract

Peptidoglycan (PG) is an essential component of the bacterial cell wall. Although experiments with organisms in vitro have yielded a wealth of information on PG synthesis and maturation, it is unclear how these studies translate to bacteria replicating within host cells. We report a chemical approach for probing PG in vivo via metabolic labeling and bioorthogonal chemistry. A wide variety of bacterial species incorporated azide and alkyne-functionalized d-alanine into their cell walls, which we visualized by covalent reaction with click chemistry probes. The d-alanine analogues were specifically incorporated into nascent PG of the intracellular pathogen Listeria monocytogenes both in vitro and during macrophage infection. Metabolic incorporation of d-alanine derivatives and click chemistry detection constitute a facile, modular platform that facilitates unprecedented spatial and temporal resolution of PG dynamics in vivo.

PMID:
23240806
PMCID:
PMC3601600
DOI:
10.1021/cb3004995
[Indexed for MEDLINE]
Free PMC Article

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