title: Synthesis and bioactivity of analogues of the marine antibiotic tropodithietic acid.
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.
authors.affiliation: Kekulé-Institut für Organische Chemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Straße 1, 53121 Bonn, Germany.
authors.forename: Patrick
authors.initials: P
authors.lastname: Rabe
authors.affiliation: Kekulé-Institut für Organische Chemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Straße 1, 53121 Bonn, Germany.
authors.forename: Tim A
authors.initials: TA
authors.lastname: Klapschinski
authors.affiliation: Kekulé-Institut für Organische Chemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Straße 1, 53121 Bonn, Germany.
authors.forename: Nelson L
authors.initials: NL
authors.lastname: Brock
authors.affiliation: Kekulé-Institut für Organische Chemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Straße 1, 53121 Bonn, Germany.
authors.forename: Christian A
authors.initials: CA
authors.lastname: Citron
authors.affiliation: Department of Systems Biology, Technical University of Denmark, Matematiktorvet bldg. 301, 2800 Kongens Lyngby, Denmark.
authors.forename: Paul
authors.initials: P
authors.lastname: D'Alvise
authors.affiliation: Department of Systems Biology, Technical University of Denmark, Matematiktorvet bldg. 301, 2800 Kongens Lyngby, Denmark.
authors.forename: Lone
authors.initials: L
authors.lastname: Gram
authors.affiliation: Kekulé-Institut für Organische Chemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Straße 1, 53121 Bonn, Germany.
authors.forename: Jeroen S
authors.initials: JS
authors.lastname: Dickschat
keywords: Roseobacter; SAR study; antibiotics; natural products; tropodithietic acid; tropone