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


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.

SUBMITTER: Siegrist MS 

PROVIDER: S-EPMC3601600 | biostudies-literature | 2013 Mar

REPOSITORIES: biostudies-literature

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

Siegrist M Sloan MS   Whiteside Sarah S   Jewett John C JC   Aditham Arjun A   Cava Felipe F   Bertozzi Carolyn R CR  

ACS chemical biology 20130111 3


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  ...[more]

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