Genomic loci for this biosynthetic pathway

Cluster Type From To
The following clusters are from record BGC0000320.1:
Cluster 1NRP135864

BGC0000320, cereulide biosynthetic gene cluster from Bacillus cereus. Locus 1. Full MIBiG entry.

Chemical compounds

Compound: Cereulide
Molecular formula: C57H96N6O18
Molecular activity: Cytotoxic
Molecular target: membrane (K+ ionophore)

Class-specific details

Biosynthetic class(es):
NRP
Cyclic depsipeptide (cyclic)
Thioesterase type:
Type I & II
Release / cyclization type:
Unknown

Nonribosomal peptide synthetases:
cesA (ABD14711.1)
Module 0
A specificity: alpha-ketoisocaproic acid
Evidence for specificity: Activity assay
C domain subtype: N/A
Scaffold-modifying domain: Other
Module is iterated
Evidence for iteration: Unknown
Module 1
A specificity: Alanine
Evidence for specificity: Sequence-based prediction
AA is epimerized
C domain subtype: LCL
Module is iterated
Evidence for iteration: Unknown
Module 2
A specificity: Unknown
Evidence for specificity: Unknown
C domain subtype: DCL
cesB (ABD14712.1)
Module 2
A specificity: alpha-ketoisovaleric acid
Evidence for specificity: Activity assay
C domain subtype: N/A
Scaffold-modifying domain: Other
Module is iterated
Evidence for iteration: Unknown
Module 3
A specificity: Valine
Evidence for specificity: Sequence-based prediction
C domain subtype: LCL
Module is iterated
Evidence for iteration: Unknown

Gene cluster description

cereulide (BGC0000320). Gene Cluster 1. Biosynthetic class = NRP. GenBank DQ360825, positions 3342-26943. Click on genes for more information.

Legend:

biosynthetic genes
transport-related genes
regulatory genes
other genes

Domain annotation

General MIBiG information on this cluster

Complete gene cluster sequence?complete
Evidence for cluster-compound connection:Knock-out studies, Enzymatic assays
MIxS-compliance:Unknown
Contact for this cluster:Monika Ehling-Schulz (Veterinary University of Vienna)

Literature references

1. Ehling-Schulz M et al. (2005) Identification and partial characterization of the nonribosomal peptide synthetase gene responsible for cereulide production in emetic Bacillus cereus. Appl Environ Microbiol 71(1):105-13. doi:
2. Ehling-Schulz M et al. (2006) Cereulide synthetase gene cluster from emetic Bacillus cereus: structure and location on a mega virulence plasmid related to Bacillus anthracis toxin plasmid pXO1. BMC Microbiol 6:20. doi: 10.1186/1471-2180-6-20.
3. Magarvey NA et al. (2006) Characterization of the cereulide NRPS alpha-hydroxy acid specifying modules: activation of alpha-keto acids and chiral reduction on the assembly line. J Am Chem Soc 128(33):10698-9. doi: 10.1021/ja0640187.
4. Rasko DA et al. (2007) Complete sequence analysis of novel plasmids from emetic and periodontal Bacillus cereus isolates reveals a common evolutionary history among the B. cereus-group plasmids, including Bacillus anthracis pXO1. J Bacteriol 189(1):52-64. doi: 10.1128/JB.01313-06. Epub 2006 Oct 13.
5. Dommel MK et al. (2010) Identification of the main promoter directing cereulide biosynthesis in emetic Bacillus cereus and its application for real-time monitoring of ces gene expression in foods. Appl Environ Microbiol 76(4):1232-40. doi: 10.1128/AEM.02317-09. Epub
6. Bauer T et al. (2010) Development of a stable isotope dilution analysis for the quantification of the Bacillus cereus toxin cereulide in foods. J Agric Food Chem 58(3):1420-8. doi: 10.1021/jf9033046.
7. Lucking G et al. (2009) Cereulide synthesis in emetic Bacillus cereus is controlled by the transition state regulator AbrB, but not by the virulence regulator PlcR. Microbiology 155(Pt 3):922-31. doi: 10.1099/mic.0.024125-0.
8. Frenzel E et al. (2012) CodY orchestrates the expression of virulence determinants in emetic Bacillus cereus by impacting key regulatory circuits. Mol Microbiol 85(1):67-88. doi: 10.1111/j.1365-2958.2012.08090.x. Epub
9. Agata N et al. (1994) A novel dodecadepsipeptide, cereulide, isolated from Bacillus cereus causes vacuole formation in HEp-2 cells. FEMS Microbiol Lett 121(1):31-4.
10. Mikkola R et al. (1999) Ionophoretic properties and mitochondrial effects of cereulide: the emetic toxin of B. cereus. Eur J Biochem 263(1):112-7.