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Synthesis of the Siderophore Coelichelin and Its Utility as a Probe in the Study of Bacterial Metal Sensing and Response.

Williams JC, Sheldon JR, Imlay HD, Dutter BF, Draelos MM, Skaar EP, Sulikowski GA
Org Lett. 2019 21 (3): 679-682

PMID: 30645132 · PMCID: PMC6474248 · DOI:10.1021/acs.orglett.8b03857

A convergent total synthesis of the siderophore coelichelin is described. The synthetic route also provided access to acetyl coelichelin and other congeners of the parent siderophore. The synthetic products were evaluated for their ability to bind ferric iron and promote growth of a siderophore-deficient strain of the Gram-negative bacterium Pseudomonas aeruginosa under iron restriction conditions. The results of these studies indicate coelichelin and several derivatives serve as ferric iron delivery vehicles for P. aeruginosa.

MeSH Terms (5)

Iron Molecular Probes Oligopeptides Pseudomonas aeruginosa Siderophores

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