ArticleScientific reports2015
Depsipeptide Intermediates Interrogate Proposed Biosynthesis of Cereulide, the Emetic Toxin of Bacillus cereus.
Article in Scientific reports, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed, 38 citations in OpenAlex.
- Genomic Insights into the Pathogenicity and Drug-Resistance of aInfection and drug resistance · 2024Article
- Cereulide and EmeticFoods (Basel, Switzerland) · 2023Review
- Genomic characterization ofFrontiers in microbiology · 2023Article
- Article
- Article
- Biosynthetic Cyclization Catalysts for the Assembly of Peptide and Polyketide Natural Products.ChemCatChem · 2021Article
- Structure Revision of Isocereulide A, an Isoform of the Food Poisoning EmeticMolecules (Basel, Switzerland) · 2021Article
- Identification of a conserved N-terminal domain in the first module of ACV synthetases.MicrobiologyOpen · 2021Article
- Article
- Signaling Natural Products from Human Pathogenic Bacteria.ACS infectious diseases · 2020Review
- TheMicrobiology spectrum · 2019Review
- Rapid detection of Bacillus ionophore cereulide in food products.Scientific reports · 2019Article
- Potassium-Ion-Selective Fluorescent Sensors To Detect Cereulide, the Emetic Toxin ofChemistryOpen · 2017Article
- Elucidating the Rimosamide-Detoxin Natural Product Families and Their Biosynthesis Using Metabolite/Gene Cluster Correlations.ACS chemical biology · 2016Article
- Evaluation of the Toxicity and Toxicokinetics of Cereulide from an Emetic Bacillus cereus Strain of Milk Origin.Toxins · 2016Article
- Temperature Exerts Control ofFrontiers in microbiology · 2016Article
- Ces locus embedded proteins control the non-ribosomal synthesis of the cereulide toxin in emetic Bacillus cereus on multiple levels.Frontiers in microbiology · 2015Article
- Food-bacteria interplay: pathometabolism of emetic Bacillus cereus.Frontiers in microbiology · 2015Review
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Authors and funding
8 authors at 4 institutions in 3 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Cereulide and isocereulides A-G are biosynthesized as emetic toxins by Bacillus cereus via a non-ribosomal peptide synthetase (NRPS) called Ces. Although a thiotemplate mechanisms involving cyclo-trimerization of ready-made D-O-Leu-D-Ala-L-O-Val-L-Val via a thioesterase (TE) domain is proposed for cereulide biosynthesis, the exact mechanism is far from being understood. UPLC-TOF MS analysis of B. cereus strains in combination with (13)C-labeling experiments now revealed tetra-, octa-, and dodecapeptides of a different sequence, namely (L-O-Val-L-Val-D-O-Leu-D-Ala)1-3, as intermediates of cereulide biosynthesis. Surprisingly, also di-, hexa-, and decadepsipeptides were identified which, together with the structures of the previously reported isocereulides E, F, and G, do not correlate to the currently proposed mechanism for cereulide biosynthesis and violate the canonical NRPS biosynthetic logic. UPLC-TOF MS metabolite analysis and bioinformatic gene cluster analysis highlighted dipeptides rather than single amino or hydroxy acids as the basic modules in tetradepsipeptide assembly and proposed the CesA C-terminal C* domain and the CesB C-terminal TE domain to function as a cooperative esterification and depsipeptide elongation center repeatedly recruiting the action of the C* domain to oligomerize tetradepsipeptides prior to the release of cereulide from the TE domain by macrocyclization.
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