4.8 Article

Discovery and Total Synthesis of Doscadenamide A: A Quorum Sensing Signaling Molecule from a Marine Cyanobacterium

Journal

ORGANIC LETTERS
Volume 21, Issue 18, Pages 7274-7278

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b02525

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Funding

  1. National Institutes of Health, National Cancer Institute [R01CA172310]
  2. National Institute of General Medical Sciences [P41GM086210]
  3. Debbie and Sylvia DeSantis Chair professorship

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Quorum sensing (QS) plays a critical role in the regulation of bacterial pathogenesis. Doscadenamide A (1a) was isolated from a marine cyanobacterium, its structure elucidated by NMR, and its activity linked to QS induction. The total synthesis of 1a was developed, and the absolute configuration confirmed through comparison of the isolated natural product with synthetic diastereomers. Our preliminary investigation indicated that 1a could activate QS signaling in a LasR-dependent manner.

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