Breakdown of 3-(allylsulfonio)propanoates in bacteria from the Roseobacter group yields garlic oil constituents

• Anuj Kumar Chhalodia and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2021, 17, 569–580, doi:10.3762/bjoc.17.51

• collapses to methanethiol (MeSH) and malonyl-CoA semialdehyde (21). This compound further degrades to acetaldehyde (22) through the thioester hydrolysis and decarboxylation [27]. Feeding of (methyl-2H6)DMSP to Phaeobacter inhibens DSM 17395 and Ruegeria pomeroyi DSM 15171 resulted in the efficient uptake of

• mutational work will be needed for more detailed insights to support our hypotheses regarding the involved enzymes in AllMSP and DAllSP breakdown and will be performed in our laboratories in the future. Experimental Strains and culture condition Phaeobacter inhibens DSM 14862, Dinoroseobacter shibae DSM

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

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

• Phaeobacter inhibens strains, revealing strain-specific mixtures. Although large differences were present between the species, the fatty acid profiles, the pool for the acyl precursors for AHL biosynthesis, were very similar. To test the acyl-chain selectivity, the three enzymes LuxI1 and LuxI2 from D. shibae

• ; fatty acid composition; N-acylhomoserine lactones; quorum sensing; Phaeobacter inhibens; Introduction The Roseobacter group, a subgroup of the Rhodobacteraceae family, constitutes an important class of Gram-negative marine bacteria, occurring in many different habitats [1][2], in fresh water as well as

• 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

• phenylalanine degradation pathway, as was shown by labeling experiments with (13C)Phe and [13C6]glucose, and incorporation into phenylacetate [81] and TDA [82]. To resolve the sulfur precursor of TDA, (34S)Cys (72) was synthesized and fed to Phaeobacter inhibens to observe an incorporation rate of 87% into both

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

• (TDA, 1a) is an antibiotic produced by the marine bacterium Phaeobacter inhibens. It has an unusual structure that is made up by a dithiet moiety fused to tropone-2-carboxylic acid (Figure 1) [1]. In Phaeobacter the compound is accompanied by hydroxy-TDA 2, while its tautomer thiotropocin (1b) was

• solutions of 1.5 g L−1 and further diluted in the bacterial growth medium, Mueller Hinton II Broth. Final concentrations ranging from 500 to 0.5 mg L−1 were tested and solvent controls were included. TDA and related natural products from Phaeobacter inhibens. Synthesis of tropone-2-carboxylic acid (13