Identification of volatiles from six marine Celeribacter strains

• Anuj Kumar Chhalodia,
• Jan Rinkel,
• Dorota Konvalinkova,
• Jörn Petersen and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2021, 17, 420–430, doi:10.3762/bjoc.17.38

• from the roseobacter group is the production of the sulfur-containing antibiotic tropodithietic acid (TDA) in Phaeobacter piscinae DSM 103509T [28], a compound that is in equilibrium with its tautomer thiotropocin [29] that was first described from Pseudomonas sp. CB-104 [30]. Its biosynthesis depends

Secondary metabolites of Bacillus subtilis impact the assembly of soil-derived semisynthetic bacterial communities

• Heiko T. Kiesewalter,
• Carlos N. Lozano-Andrade,
• Mikael L. Strube and
• Ákos T. Kovács

Beilstein J. Org. Chem. 2020, 16, 2983–2998, doi:10.3762/bjoc.16.248

• . Previous studies revealed that the introduction of SM-producing bacteria to a bacterial community had no major impact on the entire composition. The tropodithietic acid-producing marine bacterium Phaeobacter inhibens did not strongly influence the microbiome diversity of the oyster Ostrea edulis but

• of supplemented pure NRP compounds, e.g., surfactin and bacillaene. The impact of antibiotics on algae-associated bacterial communities was investigated by Geng et al. in 2016, who revealed a dose-depended influence of pure tropodithietic acid on the microbiome structure of Nannochloropsis salina [63

Acyl-group specificity of AHL synthases involved in quorum-sensing in Roseobacter group bacteria

• Lisa Ziesche,
• Jan Rinkel,
• Jeroen S. Dickschat and
• Stefan Schulz

Beilstein J. Org. Chem. 2018, 14, 1309–1316, doi:10.3762/bjoc.14.112

• regulate several physiological traits regulated by cell density, the ‘quorum’ [11][12][13][14][15][16], in roseobacters, e.g., in the production of the antibiotic tropodithietic acid in Phaeobacter inhibens [15] and cell differentiation in Dinoroseobacter shibae [14]. Roseobacter group AHLs are

Recent highlights in biosynthesis research using stable isotopes

• Jan Rinkel and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2015, 11, 2493–2508, doi:10.3762/bjoc.11.271

• study the sulfur source in tropodithietic acid (TDA, 74, Scheme 13) biosynthesis [78]. TDA is a marine antibiotic which was originally isolated from Pseudomonas species [79] showing no observable resistance in important pathogens up to now [80]. The biosynthesis of the tropone core proceeds via the

• . Oxygen atoms originating from water are labeled as Oa, whereas 18O labels in the hydroxy group of chorismate are annotated as Ob. The XanB2-reaction was not investigated (missing label). Incorporation of sulfur into tropodithietic acid (72) via cysteine. Biosynthetic proposal for the starter unit of

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 and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2014, 10, 1796–1801, doi:10.3762/bjoc.10.188

• of Denmark, Matematiktorvet bldg. 301, 2800 Kongens Lyngby, Denmark 10.3762/bjoc.10.188 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

• 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. Keywords: antibiotics; natural products; Roseobacter; SAR study; tropodithietic acid; tropone; Introduction Tropodithietic acid

• , suggesting that TDA may interact with several targets [13]. Here we report on the synthesis and bioactivity of several TDA analogues for investigating the structure–activity relationship (SAR) of this unique marine antibiotic. Results and Discussion Synthesis of analogues of tropodithietic acid For a

Isotopically labeled sulfur compounds and synthetic selenium and tellurium analogues to study sulfur metabolism in marine bacteria

• Nelson L. Brock,
• Christian A. Citron,
• Claudia Zell,
• Martine Berger,
• Irene Wagner-Döbler,
• Jörn Petersen,
• Thorsten Brinkhoff,
• Meinhard Simon and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2013, 9, 942–950, doi:10.3762/bjoc.9.108

• ]. The cooperation of phenylacetate degradation and sulfur metabolism is manifested in the production of the antibiotic tropodithietic acid (TDA, 8) [7][8] and the roseobacticides, a class of algicides, represented by, e.g., roseobacticide A (9) [9][10]. The high abundance of sulfur volatiles throughout

Algicidal lactones from the marine Roseobacter clade bacterium Ruegeria pomeroyi

• Ramona Riclea,
• Julia Gleitzmann,
• Hilke Bruns,
• Corina Junker,
• Barbara Schulz and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2012, 8, 941–950, doi:10.3762/bjoc.8.106

• bioavailability of metal ions by the formation of metal–MeSH complexes [7] and can be used for the biosynthesis of various sulfur-containing secondary metabolites [20]. A sulfur-containing metabolite, for which the direct sulfur precursor has not been determined yet, is the antibiotic tropodithietic acid (TDA, 2