Aggressively pathogenic <i>Acinetobacter baumannii</i> produce the virulence-associated siderophore acinetobactin during infection. Acinetobactin is biosynthesized and excreted in a pre-form of the molecule that isomerizes spontaneously via intramolecular attack of the hydroxamate on the electrophilic oxazoline generating an isooxazolidinone. A synthetic route to pre-acinetobactin was optimized to facilitate a detailed kinetic characterization of the first-order isomerization reaction using NMR, UV-Vis, and LCMS under a range of pH conditions. These data provide insight into the mechanism of non-enzymatic isomerization and suggest that pre-acinetobactin and acinetobactin might both function as tunable metal chelating siderophores over a broad pH range.

Nonenzymatic isomerization of acinetobactin, a siderophore from pathogenic <i>Acinetobacter baumannii</i>

249th National Meeting (2015)

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Nonenzymatic isomerization of acinetobactin, a siderophore from pathogenic Acinetobacter baumannii