D-amino acid chemical reporters reveal peptidoglycan dynamics of an intracellular pathogen

M. Sloan Siegrist, Sarah Whiteside, John C Jewett, Arjun Aditham, Felipe Cava, Carolyn R. Bertozzi

Research output: Contribution to journalArticle

113 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)500-505
Number of pages6
JournalACS Chemical Biology
Volume8
Issue number3
DOIs
StatePublished - Mar 15 2013

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Peptidoglycan
Pathogens
Amino Acids
Click Chemistry
Alanine
Cell Wall
Cells
Listeria
Alkynes
Azides
Macrophages
Listeria monocytogenes
Labeling
Bacteria
Derivatives
Infection
Experiments

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Medicine(all)

Cite this

D-amino acid chemical reporters reveal peptidoglycan dynamics of an intracellular pathogen. / Siegrist, M. Sloan; Whiteside, Sarah; Jewett, John C; Aditham, Arjun; Cava, Felipe; Bertozzi, Carolyn R.

In: ACS Chemical Biology, Vol. 8, No. 3, 15.03.2013, p. 500-505.

Research output: Contribution to journalArticle

Siegrist, M. Sloan ; Whiteside, Sarah ; Jewett, John C ; Aditham, Arjun ; Cava, Felipe ; Bertozzi, Carolyn R. / D-amino acid chemical reporters reveal peptidoglycan dynamics of an intracellular pathogen. In: ACS Chemical Biology. 2013 ; Vol. 8, No. 3. pp. 500-505.
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