Total Synthesis and Biological Investigation of (-)-Promysalin

Andrew D. Steele, Kyle W. Knouse, Colleen E. Keohane, William M. Wuest*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

26 Citations (Scopus)

Abstract

Compounds that specifically target pathogenic bacteria are greatly needed, and identifying the method by which they act would provide new avenues of treatment. Herein we report the concise, high-yielding total synthesis (eight steps, 35% yield) of promysalin, a natural product that displays antivirulence phenotypes against pathogenic bacteria. Guided by bioinformatics, four diastereomers were synthesized, and the relative and absolute stereochemistries were confirmed by spectral and biological analysis. Finally, we show for the first time that promysalin displays two antivirulence phenotypes: the dispersion of mature biofilms and the inhibition of pyoverdine production, hinting at a unique pathogenic-specific mechanism of action.

Original languageEnglish
Pages (from-to)7314-7317
Number of pages4
JournalJournal of the American Chemical Society
Volume137
Issue number23
DOIs
Publication statusPublished - 17 Jun 2015
Externally publishedYes

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