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

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