Diverted Total Synthesis of Promysalin Analogs Demonstrates That an Iron-Binding Motif Is Responsible for Its Narrow-Spectrum Antibacterial Activity

Andrew D. Steele, Colleen E. Keohane, Kyle W. Knouse, Sean E. Rossiter, Sierra J. Williams, William M. Wuest*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

Abstract

Promysalin is a species-specific Pseudomonad metabolite with unique bioactivity. To better understand the mode of action of this natural product, we synthesized 16 analogs utilizing diverted total synthesis (DTS). Our analog studies revealed that the bioactivity of promysalin is sensitive to changes within its hydrogen bond network whereby alteration has drastic biological consequences. The DTS library not only yielded three analogs that retained potency but also provided insights that resulted in the identification of a previously unknown ability of promysalin to bind iron. These findings coupled with previous observations hint at a complex multifaceted role of the natural product within the rhizosphere.

Original languageEnglish
Pages (from-to)5833-5836
Number of pages4
JournalJournal of the American Chemical Society
Volume138
Issue number18
DOIs
Publication statusPublished - 11 May 2016
Externally publishedYes

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