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ACS Chem Biol. 2010 Dec 17;5(12):1147-55. doi: 10.1021/cb100195d. Epub 2010 Oct 5.

A biosynthetic strategy for re-engineering the Staphylococcus aureus cell wall with non-native small molecules.

Author information

1
Department of Chemistry, Yale University, New Haven, Connecticut 06520, USA.

Erratum in

  • ACS Chem Biol. 2011 Sep 16;6(9):971. Kazmiercak, Barbara I [corrected to Kazmierczak, Barbara I].

Abstract

Staphylococcus aureus (S. aureus) is a Gram-positive bacterial pathogen that has emerged as a major public health threat. Here we report that the cell wall of S. aureus can be covalently re-engineered to contain non-native small molecules. This process makes use of endogenous levels of the bacterial enzyme sortase A (SrtA), which ordinarily functions to incorporate proteins into the bacterial cell wall. Thus, incubation of wild-type bacteria with rationally designed SrtA substrates results in covalent incorporation of functional molecular handles (fluorescein, biotin, and azide) into cell wall peptidoglycan. These conclusions are supported by data obtained through a variety of experimental techniques (epifluorescence and electron microscopy, biochemical extraction, and mass spectrometry), and cell-wall-incorporated azide was exploited as a chemical handle to perform an azide-alkyne cycloaddition reaction on the bacterial cell surface. This report represents the first example of cell wall engineering of S. aureus or any other pathogenic Gram-positive bacteria and has the potential for widespread utility.

PMID:
20923200
PMCID:
PMC3003768
DOI:
10.1021/cb100195d
[Indexed for MEDLINE]
Free PMC Article
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