The stereoselective synthesis of fimsbactin A, a siderophore of the human pathogen Acinetobacter baumannii, was established. Based on this synthetic route, various fimsbactin stereoisomeric analogues were generated and tested for their iron delivery activity for A. baumannii. This investigation revealed that the fimsbactin uptake machinery in this bacterium was indeed highly stereoselective in substrate recognition.

Total synthesis of anguibactin was accomplished for the first time, and the following biochemical characterizations allowed for the determination of its Fe­(III) binding mode as well as the demonstration of its iron delivery capability for Acinetobacter baumannii. These properties, in addition to the thermal stability over acinetobactin, render anguibactin as a competent surrogate siderophore that can be useful for the future development of a siderophore-based antibiotic delivery system against A. baumannii.

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