Iron is an essential nutrient that is often present at remarkably low concentrations within the environments faced by bacteria. Many bacteria synthesize siderophores, small molecule Fe(III) chelators, as a means to scavenge iron from their environment and maintain metal homeostasis. Triscatecholate siderophores, which utilize three bidentate catechol Fe(III)-binding groups, are among the most common of siderophores and are distinguished by their remarkably high ferric stability constants. We report herein a naturally diastereomeric suite of peptidic triscatecholate siderophores discovered through a genome mining platform. Interestingly the stereochemistry at Fe(III) appears to be dictated by the stereochemistry of the amino acid adjacent to the catechol Fe(III)-binding ligand. Synthetic methodology has been employed to yield derivatives of these compounds with unnatural stereochemistry as a means to uncover the factors dictating the chirality at Fe(III), while ongoing biological assays are being employed to discover the physiological relevance of Fe(III)-siderophore chirality within the native bacterial producers.<br/>

Diastereomeric suite of triscatecholate siderophores: Origin and physiological relevance of Fe(III)-complex chirality

2019 Fall National Meeting

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