Synthesis and bioactivity of analogues of the marine antibiotic tropodithietic acid

Patrick Rabe, Tim A. Klapschinski, Nelson L. Brock, Christian A. Citron, Paul D'Alvise, Lone Gram, Jeroen S. Dickschat

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    Abstract

    Tropodithietic acid (TDA) is a structurally unique sulfur-containing antibiotic from the Roseobacter clade bacterium Phaeobacter inhibens DSM 17395 and a few other related species. We have synthesised several structural analogues of TDA and used them in bioactivity tests against Staphylococcus aureus and Vibrio anguillarum for a structure-activity relationship (SAR) study, revealing that the sulfur-free analogue of TDA, tropone-2-carboxylic acid, has an antibiotic activity that is even stronger than the bioactivity of the natural product. The synthesis of this compound and of several analogues is presented and the bioactivity of the synthetic compounds is discussed.
    Original languageEnglish
    JournalBeilstein Journal of Organic Chemistry
    Volume10
    Pages (from-to)1796-1801
    Number of pages6
    ISSN2195-951X
    DOIs
    Publication statusPublished - 2014

    Bibliographical note

    This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)

    Keywords

    • CHEMISTRY,
    • PHAEOBACTER-GALLAECIENSIS
    • NATURAL-PRODUCTS
    • BIOSYNTHESIS
    • ROSEOBACTER
    • THIOTROPOCIN
    • BACTERIA
    • INHIBENS
    • TROPONE
    • REVEAL
    • NOV.
    • antibiotics
    • natural products
    • Roseobacter
    • SAR study
    • tropodithietic acid
    • tropone

    Cite this

    Rabe, P., Klapschinski, T. A., Brock, N. L., Citron, C. A., D'Alvise, P., Gram, L., & Dickschat, J. S. (2014). Synthesis and bioactivity of analogues of the marine antibiotic tropodithietic acid. Beilstein Journal of Organic Chemistry, 10, 1796-1801. https://doi.org/10.3762/bjoc.10.188