Synthesis and Characterization of Preacinetobactin and 5-Phenyl Preacinetobactin

We report the first total synthesis of 5-phenyl preacinetobactin and its characterization. The route was developed for the synthesis of preacinetobactin, the siderophore critical to the Gram-negative pathogen <i>A. baumannii</i>. It leverages a C5-substituted benzaldehyde as a key starti...

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Bibliographic Details
Main Authors: Jean M. Bray, Scott Pierce, Alfredo M. Angeles-Boza, Mark W. Peczuh
Format: Article
Language:English
Published: MDPI AG 2022-06-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/27/12/3688
Description
Summary:We report the first total synthesis of 5-phenyl preacinetobactin and its characterization. The route was developed for the synthesis of preacinetobactin, the siderophore critical to the Gram-negative pathogen <i>A. baumannii</i>. It leverages a C5-substituted benzaldehyde as a key starting material and should enable the synthesis of similar analogs. 5-Phenyl preacinetobactin binds iron in a manner analogous to the natural siderophore, but it did not rescue growth in a strain of <i>A. baumannii</i> unable to produce preacinetobactin.
ISSN:1420-3049