Genomic loci for this biosynthetic pathway

Cluster Type From To
The following clusters are from record BGC0000264.1:
Cluster 1Polyketide116662

BGC0000264, resistomycin biosynthetic gene cluster from Streptomyces resistomycificus. Locus 1. Full MIBiG entry.

Chemical compounds

Compound: resistomycin
PubChem ID: 5282060
ChemSpider ID: 4445287
SMILES string: Copy to clipboard
Molecular formula: C22H16O6
Average molecular mass: 376.364 Da
Molecular activity: Antibacterial, Inhibitor, Other
Molecular target: HIV-1 protease, RNA polymerase, DNA polymerase

Class-specific details

Biosynthetic class(es):
Polyketide
Polyketide subclass:
Other (cyclic)
Polyketide synthase subclass:
Type II
Starter unit:
Acetyl-CoA
Polyketide synthase / ketosynthase-encoding genes:
CAE51174.1
Genes involved in folding/cyclization:
CAE51171.1, CAE51178.1, CAE51181.1

Gene cluster description

resistomycin (BGC0000264). Gene Cluster 1. Biosynthetic class = Polyketide. GenBank AJ585192, positions 1-13522. Click on genes for more information.

Legend:

biosynthetic genes
transport-related genes
regulatory genes
other genes

General MIBiG information on this cluster

Complete gene cluster sequence?complete
Evidence for cluster-compound connection:Heterologous expression
MIxS-compliance:Unknown
Contact for this cluster:Keishi Ishida (Leipniz Institute for Natural Product Research and Infection Biology)

Literature references

1. Jakobi K, Hertweck C. (2004) A gene cluster encoding resistomycin biosynthesis in Streptomyces resistomycificus; exploring polyketide cyclization beyond linear and angucyclic patterns. J Am Chem Soc 126(8):2298-9. doi: 10.1021/ja0390698.
2. Ishida K et al. (2006) The boat-shaped polyketide resistoflavin results from re-facial central hydroxylation of the discoid metabolite resistomycin. J Am Chem Soc 128(45):14619-24. doi: 10.1021/ja064550u.
3. Ishida K et al. (2007) Geminal tandem C-methylation in the discoid resistomycin pathway. J Am Chem Soc 129(42):12648-9. doi: 10.1021/ja075524e. Epub 2007 Oct
4. Silvennoinen L et al. (2009) The polyketide cyclase RemF from Streptomyces resistomycificus contains an unusual octahedral zinc binding site. FEBS Lett 583(17):2917-21. doi: 10.1016/j.febslet.2009.07.061. Epub
5. Roggo BE et al. (1994) 3-Alkanoyl-5-hydroxymethyl tetronic acid homologues and resistomycin: new inhibitors of HIV-1 protease. I. Fermentation, isolation and biological activity. J Antibiot (Tokyo) 47(2):136-42.
6. Haupt I et al. (1975 TI) Effects of the antibiotic resistomycin on the synthesis of macromolecules. Z Allg Mikrobiol 15(6):411-21.
7. Shiono Y et al. (2002) Effects of polyphenolic anthrone derivatives, resistomycin and hypercin, on apoptosis in human megakaryoblastic leukemia CMK-7 cell line. Z Naturforsch C 57(9-10):923-9.
8. Gorajana A et al. (2007 TI) Resistoflavine, cytotoxic compound from a marine actinomycete, Streptomyces chibaensis AUBN1/7. Microbiol Res 162(4):322-7. doi: 10.1016/j.micres.2006.01.012. Epub 2006