Abstract
New analogs of bacterial siderophores with one, two or three catecholate moieties were synthesized using various mono- and diamino acid and dipetide scaffolds, respectively. In addition to 2,3-dihydroxybenzoyl siderophore analogs and their acylated derivatives, 3,4-dihydroxybenzoyl derivatives were prepared. Furthermore, the synthesis of a new triscatecholate serving as an intimate model for enterobactin is reported. Most of the new compounds gave a positive CAS-test and were active as siderophores tested by growth promotion assays with a set of siderophore indicator mutants under iron limitation. Structure-activity-correlations have also been studied.
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Schnabelrauch, M., Wittmann, S., Rahn, K. et al. New synthetic catecholate-type siderophores based on amino acids and dipeptides. Biometals 13, 333–348 (2000). https://doi.org/10.1023/A:1009297610755
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DOI: https://doi.org/10.1023/A:1009297610755