Genomic loci for this biosynthetic pathway

Cluster Type From To
The following clusters are from record BGC0000239.1:
Cluster 1Polyketide / Saccharide134644

BGC0000239, landomycin biosynthetic gene cluster from Streptomyces cyanogenus. Locus 1. Full MIBiG entry.

Chemical compounds

Compound: Landomycin A
PubChem ID: 368342
ChEBI ID: 70064
ChemSpider ID: 8164333
SMILES string: Copy to clipboard
Molecular formula: C55H74O22
Average molecular mass: 1087.175 Da
Molecular activity: Antibacterial, Cytotoxic
Molecular target: inhibition of DNA synthesis or interference of cellular processes critical to DNA synthesis

Class-specific details

Biosynthetic class(es):
Polyketide / Saccharide
Polyketide subclass:
Angucycline (cyclic)
Polyketide synthase subclass:
Type II
Starter unit:
Acetyl-CoA
Polyketide synthase / ketosynthase-encoding genes:
AAD13536.1,AAD13538.1
Genes involved in folding/cyclization:
AAD13535.1, AAD13540.1, AAD13552.1

Saccharide subclass:
hybrid/tailoring
Glycosyltransferases:
AAD13555.1:
Specificity: D-olivose
Evidence for specificity: Unknown
AAD13553.1:
Specificity: D-olivose
Evidence for specificity: Unknown
AAD13559.1:
Specificity: D-olivose
Evidence for specificity: Unknown
AAD13562.1:
Specificity: L-rhodinose
Evidence for specificity: Unknown

Gene cluster description

landomycin (BGC0000239). Gene Cluster 1. Biosynthetic class = Polyketide/Saccharide. GenBank AF080235. Click on genes for more information.

Legend:

biosynthetic genes
transport-related genes
regulatory genes
other genes

Homologous known gene clusters

General MIBiG information on this cluster

Complete gene cluster sequence?incomplete
Evidence for cluster-compound connection:Sequence-based prediction
MIxS-compliance:Unknown
Contact for this cluster:Andreas Bechthold (Albert-Ludwigs-Universitaet Freiburg)

Literature references

1. Westrich L et al. (1999) Cloning and characterization of a gene cluster from Streptomyces cyanogenus S136 probably involved in landomycin biosynthesis. FEMS Microbiol Lett 170(2):381-7.
2. Henkel T et al. (1990) Landomycins, new angucycline antibiotics from Streptomyces sp. I. Structural studies on landomycins A-D. J Antibiot (Tokyo) 43(5):492-503.
3. Crow RT et al. (1999) Landomycin A inhibits DNA synthesis and G1/S cell cycle progression. Bioorg Med Chem Lett 9(12):1663-6.
4. Matseliukh BP et al. (1998) [The sensitivity to landomycins A and E of streptomycetes, producers of polyketide antibiotics]. Mikrobiol Z 60(1):31-6.
5. Kharel MK et al. (2012) Elucidation of post-PKS tailoring steps involved in landomycin biosynthesis. Org Biomol Chem 10(21):4256-65. doi: 10.1039/c2ob07171a. Epub 2012
6. Ostash B et al. (2010) Properties of lanK-based regulatory circuit involved in landomycin biosynthesis in Streptomyces cyanogenus S136. Genetika 46(5):604-9.
7. Ostash I et al. (2008) Coordination of export and glycosylation of landomycins in Streptomyces cyanogenus S136. FEMS Microbiol Lett 285(2):195-202. doi:
8. Rebets Y et al. (2008) Function of lanI in regulation of landomycin A biosynthesis in Streptomyces cyanogenus S136 and cross-complementation studies with Streptomyces antibiotic regulatory proteins encoding genes. Arch Microbiol 189(2):111-20. doi: 10.1007/s00203-007-0299-5. Epub 2007
9. Ostash B et al. (2004) Generation of new landomycins by combinatorial biosynthetic manipulation of the LndGT4 gene of the landomycin E cluster in S. globisporus. Chem Biol 11(4):547-55. doi: 10.1016/j.chembiol.2004.03.011.
10. Henkel T et al. (1990) Landomycins, new angucycline antibiotics from Streptomyces sp. I. Structural studies on landomycins A-D. J Antibiot (Tokyo) 43(5):492-503.
11. Mayer A et al. (2005) LanV, a bifunctional enzyme: aromatase and ketoreductase during landomycin A biosynthesis. Chembiochem 6(12):2312-5. doi: 10.1002/cbic.200500205.
12. Luzhetskyy A et al. (2005) Iteratively acting glycosyltransferases involved in the hexasaccharide biosynthesis of landomycin A. Chem Biol 12(7):725-9. doi: 10.1016/j.chembiol.2005.05.008.
13. Erb A et al. (2009) Differences in the substrate specificity of glycosyltransferases involved in landomycins A and E biosynthesis. Appl Microbiol Biotechnol 83(6):1067-76. doi:
14. Tam HK et al. (2015) Structural characterization of O- and C-glycosylating variants of the landomycin glycosyltransferase LanGT2. Angew Chem Int Ed Engl 54(9):2811-5. doi: 10.1002/anie.201409792.
15. Harle J et al. (2011) Rational design of an aryl-C-glycoside catalyst from a natural product O-glycosyltransferase. Chem Biol 18(4):520-30. doi: 10.1016/j.chembiol.2011.02.013.
16. Trefzer A et al. (2001) Elucidation of the function of two glycosyltransferase genes (lanGT1 and lanGT4) involved in landomycin biosynthesis and generation of new oligosaccharide antibiotics. Chem Biol 8(12):1239-52.
17. Luzhetskyy A et al. (2005) LanGT2 Catalyzes the First Glycosylation Step during landomycin A biosynthesis. Chembiochem 6(8):1406-10. doi: 10.1002/cbic.200500018.
18. Luzhetskyy A et al. (2004) Function of lanGT3, a glycosyltransferase gene involved in landomycin A biosynthesis. Chembiochem 5(11):1567-70. doi: 10.1002/cbic.200400123.