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.
Bibliographical noteThis 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)
- natural products
- SAR study
- tropodithietic acid
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