Rabe, Patrick3; Klapschinski, Tim A.3; Brock, Nelson L.3; Citron, Christian A.3; D'Alvise, Paul1; Gram, Lone4; Dickschat, Jeroen S.3
1 Department of Systems Biology, Technical University of Denmark2 Bacterial Ecophysiology and Biotechnology, Department of Systems Biology, Technical University of Denmark3 Rheinische Friedrich-Wilhelms-Universität Bonn4 Bacterial Ecophysiology and Biotechnology, Department of Biotechnology and Biomedicine, Technical University of Denmark
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.
Beilstein Journal of Organic Chemistry, 2014, Vol 10, p. 1796-1801