Genomic loci for this biosynthetic pathway

Cluster Type From To
The following clusters are from record BGC0000276.1:
Cluster 1Polyketide / Saccharide111790
The following clusters are from record BGC0000276.2:
Cluster 2Polyketide / Saccharide18018
The following clusters are from record BGC0000276.3:
Cluster 3Polyketide / Saccharide15408
The following clusters are from record BGC0000276.4:
Cluster 4Polyketide / Saccharide15700

BGC0000276, urdamycin biosynthetic gene cluster from Streptomyces fradiae. Locus 1. Full MIBiG entry.

Chemical compounds

Compound: Urdamycin A
ChEBI ID: 32279
SMILES string: Copy to clipboard
Molecular formula: C43H56O17
Average molecular mass: 844.89454 Da
Molecular activity: Antibacterial, Cytotoxic, Other

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:
CAA60569.1,CAA60571.1
Genes involved in folding/cyclization:
CAA60568.1, AAF00205.1,

Saccharide subclass:
hybrid/tailoring
Glycosyltransferases:
AAF00209.1:
Specificity: D-olivose
Evidence for specificity: Knock-out construct
Sugar biosynthesis subcluster: AAF72551.1
AAF00214.1:
Specificity: L-rhodinose
Evidence for specificity: Knock-out construct
Sugar biosynthesis subcluster: AAF72549.1, AAF72550.1, AAF00208.1
AAF00215.1:
Specificity: D-olivose
Evidence for specificity: Knock-out construct
Sugar biosynthesis subcluster: AAF72551.1
AAF00217.1:
Specificity: L-rhodinose
Evidence for specificity: Unknown
Sugar biosynthesis subcluster: AAF72549.1, AAF72550.1, AAF00208.1

Gene cluster description

urdamycin (BGC0000276). Gene Cluster 1. Biosynthetic class = Polyketide/Saccharide. GenBank AF164961. 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:Knock-out studies
MIxS-compliance:Unknown
Contact for this cluster:Andreas Bechthold (Albert-Ludwigs-Universitaet Freiburg)

Literature references

1. Drautz H et al. (1986) Metabolic products of microorganisms. 234. Urdamycins, new angucycline antibiotics from Streptomyces fradiae. I. Isolation, characterization and biological properties. J Antibiot (Tokyo) 39(12):1657-69.
2. Henkel T et al. (1989) Urdamycins, new angucycline antibiotics from Streptomyces fradiae. V. Derivatives of urdamycin A. J Antibiot (Tokyo) 42(2):299-311.
3. Rohr J et al. (1989) Urdamycins, new angucycline antibiotics from Streptomyces fradiae. IV. Biosynthetic studies of urdamycins A-D. J Antibiot (Tokyo) 42(7):1151-7.
4. Decker H, Haag S. (1995) Cloning and characterization of a polyketide synthase gene from Streptomyces fradiae Tu2717, which carries the genes for biosynthesis of the angucycline antibiotic urdamycin A and a gene probably involved in its oxygenation. J Bacteriol 177(21):6126-36.
5. Faust B et al. (2000) Two new tailoring enzymes, a glycosyltransferase and an oxygenase, involved in biosynthesis of the angucycline antibiotic urdamycin A in Streptomyces fradiae Tu2717. Microbiology 146 ( Pt 1):147-54. doi: 10.1099/00221287-146-1-147.
6. Trefzer A et al. (2000) Function of glycosyltransferase genes involved in urdamycin A biosynthesis. Chem Biol 7(2):133-42.
7. Hoffmeister D et al. (2000) The NDP-sugar co-substrate concentration and the enzyme expression level influence the substrate specificity of glycosyltransferases: cloning and characterization of deoxysugar biosynthetic genes of the urdamycin biosynthetic gene cluster. Chem Biol 7(11):821-31.
8. Hoffmeister D et al. (2001) Two sequence elements of glycosyltransferases involved in urdamycin biosynthesis are responsible for substrate specificity and enzymatic activity. Chem Biol 8(6):557-67.
9. Hoffmeister D et al. (2002) Engineered urdamycin glycosyltransferases are broadened and altered in substrate specificity. Chem Biol 9(3):287-95.
10. Trefzer A et al. (2002) Rationally designed glycosylated premithramycins: hybrid aromatic polyketides using genes from three different biosynthetic pathways. J Am Chem Soc 124(21):6056-62.
11. Rix U et al. (2003) Urdamycin L: a novel metabolic shunt product that provides evidence for the role of the urdM gene in the urdamycin A biosynthetic pathway of Streptomyces fradiae TU 2717. Chembiochem 4(1):109-11. doi: 10.1002/cbic.200390002.
12. Hoffmeister D et al. (2003) The C-Glycosyltransferase UrdGT2 is unselective toward d- and l-configured nucleotide-bound rhodinoses. J Am Chem Soc 125(16):4678-9. doi: 10.1021/ja029645k.
13. Fedoryshyn M et al. (2007) Surprising production of a new urdamycin derivative by S. fradiae Delta urdQ/R. J Biotechnol 130(1):32-8. doi: 10.1016/j.jbiotec.2007.02.018. Epub
14. Mittler M et al. (2007) Structure and action of the C-C bond-forming glycosyltransferase UrdGT2 involved in the biosynthesis of the antibiotic urdamycin. J Mol Biol 372(1):67-76. doi: 10.1016/j.jmb.2007.06.005. Epub 2007
15. Hayakawa Y et al. (1985) Studies on the isotetracenone antibiotics. II. Kerriamycins A, B and C, new antitumor antibiotics. J Antibiot (Tokyo) 38(7):960-3.
16. Fukuda I et al. (2009) Kerriamycin B inhibits protein SUMOylation. J Antibiot (Tokyo) 62(4):221-4. doi: 10.1038/ja.2009.10. Epub 2009 Mar

BGC0000276, urdamycin biosynthetic gene cluster from Streptomyces fradiae. Locus 2. Full MIBiG entry.

Chemical compounds

Compound: Urdamycin A
ChEBI ID: 32279
SMILES string: Copy to clipboard
Molecular formula: C43H56O17
Average molecular mass: 844.89454 Da
Molecular activity: Antibacterial, Cytotoxic, Other

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:
CAA60569.1,CAA60571.1
Genes involved in folding/cyclization:
CAA60568.1, AAF00205.1,

Saccharide subclass:
hybrid/tailoring
Glycosyltransferases:
AAF00209.1:
Specificity: D-olivose
Evidence for specificity: Knock-out construct
Sugar biosynthesis subcluster: AAF72551.1
AAF00214.1:
Specificity: L-rhodinose
Evidence for specificity: Knock-out construct
Sugar biosynthesis subcluster: AAF72549.1, AAF72550.1, AAF00208.1
AAF00215.1:
Specificity: D-olivose
Evidence for specificity: Knock-out construct
Sugar biosynthesis subcluster: AAF72551.1
AAF00217.1:
Specificity: L-rhodinose
Evidence for specificity: Unknown
Sugar biosynthesis subcluster: AAF72549.1, AAF72550.1, AAF00208.1

Gene cluster description

urdamycin (BGC0000276). Gene Cluster 2. Biosynthetic class = Polyketide/Saccharide. GenBank AF164960. 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:Knock-out studies
MIxS-compliance:Unknown
Contact for this cluster:Andreas Bechthold (Albert-Ludwigs-Universitaet Freiburg)

Literature references

1. Drautz H et al. (1986) Metabolic products of microorganisms. 234. Urdamycins, new angucycline antibiotics from Streptomyces fradiae. I. Isolation, characterization and biological properties. J Antibiot (Tokyo) 39(12):1657-69.
2. Henkel T et al. (1989) Urdamycins, new angucycline antibiotics from Streptomyces fradiae. V. Derivatives of urdamycin A. J Antibiot (Tokyo) 42(2):299-311.
3. Rohr J et al. (1989) Urdamycins, new angucycline antibiotics from Streptomyces fradiae. IV. Biosynthetic studies of urdamycins A-D. J Antibiot (Tokyo) 42(7):1151-7.
4. Decker H, Haag S. (1995) Cloning and characterization of a polyketide synthase gene from Streptomyces fradiae Tu2717, which carries the genes for biosynthesis of the angucycline antibiotic urdamycin A and a gene probably involved in its oxygenation. J Bacteriol 177(21):6126-36.
5. Faust B et al. (2000) Two new tailoring enzymes, a glycosyltransferase and an oxygenase, involved in biosynthesis of the angucycline antibiotic urdamycin A in Streptomyces fradiae Tu2717. Microbiology 146 ( Pt 1):147-54. doi: 10.1099/00221287-146-1-147.
6. Trefzer A et al. (2000) Function of glycosyltransferase genes involved in urdamycin A biosynthesis. Chem Biol 7(2):133-42.
7. Hoffmeister D et al. (2000) The NDP-sugar co-substrate concentration and the enzyme expression level influence the substrate specificity of glycosyltransferases: cloning and characterization of deoxysugar biosynthetic genes of the urdamycin biosynthetic gene cluster. Chem Biol 7(11):821-31.
8. Hoffmeister D et al. (2001) Two sequence elements of glycosyltransferases involved in urdamycin biosynthesis are responsible for substrate specificity and enzymatic activity. Chem Biol 8(6):557-67.
9. Hoffmeister D et al. (2002) Engineered urdamycin glycosyltransferases are broadened and altered in substrate specificity. Chem Biol 9(3):287-95.
10. Trefzer A et al. (2002) Rationally designed glycosylated premithramycins: hybrid aromatic polyketides using genes from three different biosynthetic pathways. J Am Chem Soc 124(21):6056-62.
11. Rix U et al. (2003) Urdamycin L: a novel metabolic shunt product that provides evidence for the role of the urdM gene in the urdamycin A biosynthetic pathway of Streptomyces fradiae TU 2717. Chembiochem 4(1):109-11. doi: 10.1002/cbic.200390002.
12. Hoffmeister D et al. (2003) The C-Glycosyltransferase UrdGT2 is unselective toward d- and l-configured nucleotide-bound rhodinoses. J Am Chem Soc 125(16):4678-9. doi: 10.1021/ja029645k.
13. Fedoryshyn M et al. (2007) Surprising production of a new urdamycin derivative by S. fradiae Delta urdQ/R. J Biotechnol 130(1):32-8. doi: 10.1016/j.jbiotec.2007.02.018. Epub
14. Mittler M et al. (2007) Structure and action of the C-C bond-forming glycosyltransferase UrdGT2 involved in the biosynthesis of the antibiotic urdamycin. J Mol Biol 372(1):67-76. doi: 10.1016/j.jmb.2007.06.005. Epub 2007
15. Hayakawa Y et al. (1985) Studies on the isotetracenone antibiotics. II. Kerriamycins A, B and C, new antitumor antibiotics. J Antibiot (Tokyo) 38(7):960-3.
16. Fukuda I et al. (2009) Kerriamycin B inhibits protein SUMOylation. J Antibiot (Tokyo) 62(4):221-4. doi: 10.1038/ja.2009.10. Epub 2009 Mar

BGC0000276, urdamycin biosynthetic gene cluster from Streptomyces fradiae. Locus 3. Full MIBiG entry.

Chemical compounds

Compound: Urdamycin A
ChEBI ID: 32279
SMILES string: Copy to clipboard
Molecular formula: C43H56O17
Average molecular mass: 844.89454 Da
Molecular activity: Antibacterial, Cytotoxic, Other

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:
CAA60569.1,CAA60571.1
Genes involved in folding/cyclization:
CAA60568.1, AAF00205.1,

Saccharide subclass:
hybrid/tailoring
Glycosyltransferases:
AAF00209.1:
Specificity: D-olivose
Evidence for specificity: Knock-out construct
Sugar biosynthesis subcluster: AAF72551.1
AAF00214.1:
Specificity: L-rhodinose
Evidence for specificity: Knock-out construct
Sugar biosynthesis subcluster: AAF72549.1, AAF72550.1, AAF00208.1
AAF00215.1:
Specificity: D-olivose
Evidence for specificity: Knock-out construct
Sugar biosynthesis subcluster: AAF72551.1
AAF00217.1:
Specificity: L-rhodinose
Evidence for specificity: Unknown
Sugar biosynthesis subcluster: AAF72549.1, AAF72550.1, AAF00208.1

Gene cluster description

urdamycin (BGC0000276). Gene Cluster 3. Biosynthetic class = Polyketide/Saccharide. GenBank AF269227. 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:Knock-out studies
MIxS-compliance:Unknown
Contact for this cluster:Andreas Bechthold (Albert-Ludwigs-Universitaet Freiburg)

Literature references

1. Drautz H et al. (1986) Metabolic products of microorganisms. 234. Urdamycins, new angucycline antibiotics from Streptomyces fradiae. I. Isolation, characterization and biological properties. J Antibiot (Tokyo) 39(12):1657-69.
2. Henkel T et al. (1989) Urdamycins, new angucycline antibiotics from Streptomyces fradiae. V. Derivatives of urdamycin A. J Antibiot (Tokyo) 42(2):299-311.
3. Rohr J et al. (1989) Urdamycins, new angucycline antibiotics from Streptomyces fradiae. IV. Biosynthetic studies of urdamycins A-D. J Antibiot (Tokyo) 42(7):1151-7.
4. Decker H, Haag S. (1995) Cloning and characterization of a polyketide synthase gene from Streptomyces fradiae Tu2717, which carries the genes for biosynthesis of the angucycline antibiotic urdamycin A and a gene probably involved in its oxygenation. J Bacteriol 177(21):6126-36.
5. Faust B et al. (2000) Two new tailoring enzymes, a glycosyltransferase and an oxygenase, involved in biosynthesis of the angucycline antibiotic urdamycin A in Streptomyces fradiae Tu2717. Microbiology 146 ( Pt 1):147-54. doi: 10.1099/00221287-146-1-147.
6. Trefzer A et al. (2000) Function of glycosyltransferase genes involved in urdamycin A biosynthesis. Chem Biol 7(2):133-42.
7. Hoffmeister D et al. (2000) The NDP-sugar co-substrate concentration and the enzyme expression level influence the substrate specificity of glycosyltransferases: cloning and characterization of deoxysugar biosynthetic genes of the urdamycin biosynthetic gene cluster. Chem Biol 7(11):821-31.
8. Hoffmeister D et al. (2001) Two sequence elements of glycosyltransferases involved in urdamycin biosynthesis are responsible for substrate specificity and enzymatic activity. Chem Biol 8(6):557-67.
9. Hoffmeister D et al. (2002) Engineered urdamycin glycosyltransferases are broadened and altered in substrate specificity. Chem Biol 9(3):287-95.
10. Trefzer A et al. (2002) Rationally designed glycosylated premithramycins: hybrid aromatic polyketides using genes from three different biosynthetic pathways. J Am Chem Soc 124(21):6056-62.
11. Rix U et al. (2003) Urdamycin L: a novel metabolic shunt product that provides evidence for the role of the urdM gene in the urdamycin A biosynthetic pathway of Streptomyces fradiae TU 2717. Chembiochem 4(1):109-11. doi: 10.1002/cbic.200390002.
12. Hoffmeister D et al. (2003) The C-Glycosyltransferase UrdGT2 is unselective toward d- and l-configured nucleotide-bound rhodinoses. J Am Chem Soc 125(16):4678-9. doi: 10.1021/ja029645k.
13. Fedoryshyn M et al. (2007) Surprising production of a new urdamycin derivative by S. fradiae Delta urdQ/R. J Biotechnol 130(1):32-8. doi: 10.1016/j.jbiotec.2007.02.018. Epub
14. Mittler M et al. (2007) Structure and action of the C-C bond-forming glycosyltransferase UrdGT2 involved in the biosynthesis of the antibiotic urdamycin. J Mol Biol 372(1):67-76. doi: 10.1016/j.jmb.2007.06.005. Epub 2007
15. Hayakawa Y et al. (1985) Studies on the isotetracenone antibiotics. II. Kerriamycins A, B and C, new antitumor antibiotics. J Antibiot (Tokyo) 38(7):960-3.
16. Fukuda I et al. (2009) Kerriamycin B inhibits protein SUMOylation. J Antibiot (Tokyo) 62(4):221-4. doi: 10.1038/ja.2009.10. Epub 2009 Mar

BGC0000276, urdamycin biosynthetic gene cluster from Streptomyces fradiae. Locus 4. Full MIBiG entry.

Chemical compounds

Compound: Urdamycin A
ChEBI ID: 32279
SMILES string: Copy to clipboard
Molecular formula: C43H56O17
Average molecular mass: 844.89454 Da
Molecular activity: Antibacterial, Cytotoxic, Other

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:
CAA60569.1,CAA60571.1
Genes involved in folding/cyclization:
CAA60568.1, AAF00205.1,

Saccharide subclass:
hybrid/tailoring
Glycosyltransferases:
AAF00209.1:
Specificity: D-olivose
Evidence for specificity: Knock-out construct
Sugar biosynthesis subcluster: AAF72551.1
AAF00214.1:
Specificity: L-rhodinose
Evidence for specificity: Knock-out construct
Sugar biosynthesis subcluster: AAF72549.1, AAF72550.1, AAF00208.1
AAF00215.1:
Specificity: D-olivose
Evidence for specificity: Knock-out construct
Sugar biosynthesis subcluster: AAF72551.1
AAF00217.1:
Specificity: L-rhodinose
Evidence for specificity: Unknown
Sugar biosynthesis subcluster: AAF72549.1, AAF72550.1, AAF00208.1

Gene cluster description

urdamycin (BGC0000276). Gene Cluster 4. Biosynthetic class = Polyketide/Saccharide. GenBank X87093. 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:Knock-out studies
MIxS-compliance:Unknown
Contact for this cluster:Andreas Bechthold (Albert-Ludwigs-Universitaet Freiburg)

Literature references

1. Drautz H et al. (1986) Metabolic products of microorganisms. 234. Urdamycins, new angucycline antibiotics from Streptomyces fradiae. I. Isolation, characterization and biological properties. J Antibiot (Tokyo) 39(12):1657-69.
2. Henkel T et al. (1989) Urdamycins, new angucycline antibiotics from Streptomyces fradiae. V. Derivatives of urdamycin A. J Antibiot (Tokyo) 42(2):299-311.
3. Rohr J et al. (1989) Urdamycins, new angucycline antibiotics from Streptomyces fradiae. IV. Biosynthetic studies of urdamycins A-D. J Antibiot (Tokyo) 42(7):1151-7.
4. Decker H, Haag S. (1995) Cloning and characterization of a polyketide synthase gene from Streptomyces fradiae Tu2717, which carries the genes for biosynthesis of the angucycline antibiotic urdamycin A and a gene probably involved in its oxygenation. J Bacteriol 177(21):6126-36.
5. Faust B et al. (2000) Two new tailoring enzymes, a glycosyltransferase and an oxygenase, involved in biosynthesis of the angucycline antibiotic urdamycin A in Streptomyces fradiae Tu2717. Microbiology 146 ( Pt 1):147-54. doi: 10.1099/00221287-146-1-147.
6. Trefzer A et al. (2000) Function of glycosyltransferase genes involved in urdamycin A biosynthesis. Chem Biol 7(2):133-42.
7. Hoffmeister D et al. (2000) The NDP-sugar co-substrate concentration and the enzyme expression level influence the substrate specificity of glycosyltransferases: cloning and characterization of deoxysugar biosynthetic genes of the urdamycin biosynthetic gene cluster. Chem Biol 7(11):821-31.
8. Hoffmeister D et al. (2001) Two sequence elements of glycosyltransferases involved in urdamycin biosynthesis are responsible for substrate specificity and enzymatic activity. Chem Biol 8(6):557-67.
9. Hoffmeister D et al. (2002) Engineered urdamycin glycosyltransferases are broadened and altered in substrate specificity. Chem Biol 9(3):287-95.
10. Trefzer A et al. (2002) Rationally designed glycosylated premithramycins: hybrid aromatic polyketides using genes from three different biosynthetic pathways. J Am Chem Soc 124(21):6056-62.
11. Rix U et al. (2003) Urdamycin L: a novel metabolic shunt product that provides evidence for the role of the urdM gene in the urdamycin A biosynthetic pathway of Streptomyces fradiae TU 2717. Chembiochem 4(1):109-11. doi: 10.1002/cbic.200390002.
12. Hoffmeister D et al. (2003) The C-Glycosyltransferase UrdGT2 is unselective toward d- and l-configured nucleotide-bound rhodinoses. J Am Chem Soc 125(16):4678-9. doi: 10.1021/ja029645k.
13. Fedoryshyn M et al. (2007) Surprising production of a new urdamycin derivative by S. fradiae Delta urdQ/R. J Biotechnol 130(1):32-8. doi: 10.1016/j.jbiotec.2007.02.018. Epub
14. Mittler M et al. (2007) Structure and action of the C-C bond-forming glycosyltransferase UrdGT2 involved in the biosynthesis of the antibiotic urdamycin. J Mol Biol 372(1):67-76. doi: 10.1016/j.jmb.2007.06.005. Epub 2007
15. Hayakawa Y et al. (1985) Studies on the isotetracenone antibiotics. II. Kerriamycins A, B and C, new antitumor antibiotics. J Antibiot (Tokyo) 38(7):960-3.
16. Fukuda I et al. (2009) Kerriamycin B inhibits protein SUMOylation. J Antibiot (Tokyo) 62(4):221-4. doi: 10.1038/ja.2009.10. Epub 2009 Mar