Genomic loci for this biosynthetic pathway

Cluster Type From To
The following clusters are from record BGC0000017.1:
Cluster 1Polyketide / Alkaloid128910

BGC0000017, anatoxin biosynthetic gene cluster from [Oscillatoria] sp. PCC. Locus 1. Full MIBiG entry.

Chemical compounds

Compound: Anatoxin-a
PubChem ID: 3034748
SMILES string: Copy to clipboard
Molecular formula: C10H15NO
Average molecular mass: 165.236 Da
Molecular activity: Other
Molecular target: Nicotinic acetylcholine receptor

Class-specific details

Biosynthetic class(es):
Polyketide / Alkaloid
Polyketide subclass:
Other (cyclic)
Polyketide synthase subclass:
Modular type I
Starter unit:
Other
Thioesterase type:
Type II
Release / cyclization type:
Unknown

Modular polyketide synthases:
anaE
Module 1
AT specificity: Unknown
Evidence for specificity: Unknown
KR stereochemistry: Unknown

anaF
Module 2
AT specificity: Unknown
Evidence for specificity: Unknown
KR stereochemistry: Unknown

anaG
Module 3
AT specificity: Unknown
Evidence for specificity: Unknown

Alkaloid subclass:
Other

Gene cluster description

anatoxin (BGC0000017). Gene Cluster 1. Biosynthetic class = Polyketide/Alkaloid. GenBank FJ477836. Click on genes for more information.

Legend:

biosynthetic genes
transport-related genes
regulatory genes
other genes

Domain annotation

Homologous known gene clusters

General MIBiG information on this cluster

Complete gene cluster sequence?complete
Evidence for cluster-compound connection:Enzymatic assays, Sequence-based prediction
MIxS-compliance:Unknown
Contact for this cluster:Olivier Ploux (University Paris Diderot)

Literature references

1. Mejean A et al. (2014) Biosynthesis of anatoxin-a and analogues (anatoxins) in cyanobacteria. Toxicon 91:15-22. doi: 10.1016/j.toxicon.2014.07.016. Epub 2014 Aug 6.
2. Moncoq K et al. (2013) Structure of the prolyl-acyl carrier protein oxidase involved in the biosynthesis of the cyanotoxin anatoxin-a. Acta Crystallogr D Biol Crystallogr 69(Pt 12):2340-52. doi:
3. Mann S et al. (2011) Insights into the reaction mechanism of the prolyl-acyl carrier protein oxidase involved in anatoxin-a and homoanatoxin-a biosynthesis. Biochemistry 50(33):7184-97. doi: 10.1021/bi200892a. Epub 2011 Jul
4. Mejean A et al. (2010) The genome sequence of the cyanobacterium Oscillatoria sp. PCC 6506 reveals several gene clusters responsible for the biosynthesis of toxins and secondary metabolites. J Bacteriol 192(19):5264-5. doi: 10.1128/JB.00704-10. Epub 2010 Jul 30.
5. Mejean A et al. (2010) In vitro reconstitution of the first steps of anatoxin-a biosynthesis in Oscillatoria PCC 6506: from free L-proline to acyl carrier protein bound dehydroproline. Biochemistry 49(1):103-13. doi: 10.1021/bi9018785.
6. Mejean A et al. (2009) Evidence that biosynthesis of the neurotoxic alkaloids anatoxin-a and homoanatoxin-a in the cyanobacterium Oscillatoria PCC 6506 occurs on a modular polyketide synthase initiated by L-proline. J Am Chem Soc 131(22):7512-3. doi: 10.1021/ja9024353.
7. Cadel-Six S et al. (2009) Identification of a polyketide synthase coding sequence specific for anatoxin-a-producing Oscillatoria cyanobacteria. Appl Environ Microbiol 75(14):4909-12. doi: 10.1128/AEM.02478-08. Epub
8. Rantala-Ylinen A et al. (2011) Anatoxin-a synthetase gene cluster of the cyanobacterium Anabaena sp. strain 37 and molecular methods to detect potential producers. Appl Environ Microbiol 77(20):7271-8. doi: 10.1128/AEM.06022-11. Epub
9. Shih PM et al. (2013) Improving the coverage of the cyanobacterial phylum using diversity-driven genome sequencing. Proc Natl Acad Sci U S A 110(3):1053-8. doi: