Genomic loci for this biosynthetic pathway

Cluster Type From To
The following clusters are from record BGC0000958.1:
Cluster 1NRP / Polyketide124626

BGC0000958, antimycin biosynthetic gene cluster from Streptomyces sp. S4. Locus 1. Full MIBiG entry.

Chemical compounds

Compound: Antimycin
PubChem ID: 14957
SMILES string: Copy to clipboard
Molecular formula: C28H40N2O9
Average molecular mass: 548.633 Da
Molecular activity: Antifungal, Cytotoxic
Molecular target: Bcl-XL,cytochrome C reductase

Class-specific details

Biosynthetic class(es):
NRP / Polyketide
Cyclic depsipeptide (cyclic)
Thioesterase type:
None
Release / cyclization type:
Macrolactonization

Nonribosomal peptide synthetases:
antF (ZP_09179982.1)
Module 0
A specificity: Unknown
Evidence for specificity: Unknown
C domain subtype: Starter
antG (ZP_09179983.1)
Module 0
A specificity: Unknown
Evidence for specificity: Unknown
C domain subtype: N/A
antC (ZP_09179979.1)
Module 1
A specificity: Threonine
Evidence for specificity: Activity assay
C domain subtype: Starter
Module 2
A specificity: Pyruvate
Evidence for specificity: Activity assay
C domain subtype: LCL
Polyketide subclass:
Other (cyclic)
Polyketide synthase subclass:
Modular type I
Starter unit:
Other
Thioesterase type:
None
Release / cyclization type:
Macrolactamization

Modular polyketide synthases:
antD (ZP_09179980.1)
Module 3
AT specificity: Various atypical acyl-CoAs
Evidence for specificity: Activity assay
Scaffold-modifying domain: None

antM (ZP_09179989.1)
Module 3
KR stereochemistry: Unknown
Scaffold-modifying domain: None

Gene cluster description

antimycin (BGC0000958). Gene Cluster 1. Biosynthetic class = NRP/Polyketide. GenBank NZ_FR873698, positions 81953-106578. 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:Knock-out studies, Enzymatic assays, Heterologous expression, Gene expression correlated with compound production, Sequence-based prediction
MIxS-compliance:Unknown
Contact for this cluster:Ryan F. Seipke (University of Leeds)

Literature references

1. Seipke RF et al. (2011 TI) A single Streptomyces symbiont makes multiple antifungals to support the fungus farming ant Acromyrmex octospinosus. PLoS One 6(8):e22028. doi: 10.1371/journal.pone.0022028. Epub 2011 Aug 3.
2. Schoenian I et al. (2012) An unprecedented 1,2-shift in the biosynthesis of the 3-aminosalicylate moiety of antimycins. Chembiochem 13(6):769-73. doi: 10.1002/cbic.201200033. Epub 2012 Feb
3. Yan Y et al. (2012) Biosynthetic pathway for high structural diversity of a common dilactone core in antimycin production. Org Lett 14(16):4142-5. doi: 10.1021/ol301785x. Epub 2012 Aug 3.
4. Sandy M et al. (2012) Enzymatic synthesis of dilactone scaffold of antimycins. ACS Chem Biol 7(12):1956-61. doi: 10.1021/cb300416w. Epub 2012 Sep
5. Sandy M et al. (2013) Characterization of AntB, a promiscuous acyltransferase involved in antimycin biosynthesis. Org Lett 15(13):3396-9. doi: 10.1021/ol4014365. Epub 2013 Jun 17.
6. Yan Y et al. (2013) Multiplexing of combinatorial chemistry in antimycin biosynthesis: expansion of molecular diversity and utility. Angew Chem Int Ed Engl 52(47):12308-12. doi: 10.1002/anie.201305569.
7. Liu J et al. (2015) Biosynthesis of antimycins with a reconstituted 3-formamidosalicylate pharmacophore in Escherichia coli. ACS Synth Biol 4(5):559-65. doi: 10.1021/sb5003136. Epub 2014 Oct 7.
8. Seipke RF, Hutchings MI. (2013) The regulation and biosynthesis of antimycins. Beilstein J Org Chem 9:2556-63. doi: 10.3762/bjoc.9.290.
9. Tzung SP et al. (2001) Antimycin A mimics a cell-death-inducing Bcl-2 homology domain 3. Nat Cell Biol 3(2):183-91. doi: 10.1038/35055095.
10. TAPPEL AL. (1960) Inhibition of electron transport by antimycin A, alkyl hydroxy naphthoquinones and metal coordination compounds. Biochem Pharmacol 3:289-96.