close all open/close all
Jump cluster list

Cluster information : Nogalamycin


close this sectionCompound

Entry nameNogalamycin
PKS TypeTypeII
Starter Unitacetyl-CoA
Chain Length10
Sugar Unitnogalamine
nogalose
ClassificationAnthracycline
ActivityAntibacterial
Antitumor
Toxic
CompositionC39H49NO16
Nogalamycin

close this sectionOriginal source

Organism
StrainATCC 27451 (=NBRC 13445)
Contig

Click on the icon to see Genetic map.

close this sectionPKS/NRPS Module

KS7..380
CLF4..362
ACP6..79

close this sectionReference

A gene cluster involved in nogalamycin biosynthesis from Streptomyces nogalater: sequence analysis and complementation of early-block mutations in the anthracycline pathway.
Ylihonko K, Tuikkanen J, Jussila S, Cong L, Mantsala P
[PMID: 8668120]Mol Gen Genet. 251 (1996) 113-20
Isolation and characterization of 8-demethoxy steffimycins and generation of 2,8-demethoxy steffimycins in Streptomyces steffisburgensis by the nogalamycin biosynthesis genes.
Kunnari T, Tuikkanen J, Hautala A, Hakala J, Ylihonko K, Mantsala P
[PMID: 9268006]J Antibiot (Tokyo). 50 (1997) 496-501
Characterization of Streptomyces nogalater genes encoding enzymes involved in glycosylation steps in nogalamycin biosynthesis.
Torkkell S, Ylihonko K, Hakala J, Skurnik M, Mantsala P
[PMID: 9349712]Mol Gen Genet. 256 (1997) 203-9
Identification of a cyclase gene dictating the C-9 stereochemistry of anthracyclines from Streptomyces nogalater.
Torkkell S, Kunnari T, Palmu K, Hakala J, Mantsala P, Ylihonko K
[PMID: 10639368]Antimicrob Agents Chemother. 44 (2000) 396-9
The entire nogalamycin biosynthetic gene cluster of Streptomyces nogalater: characterization of a 20-kb DNA region and generation of hybrid structures.
Torkkell S, Kunnari T, Palmu K, Mantsala P, Hakala J, Ylihonko K
[PMID: 11683270]Mol Genet Genomics. 266 (2001) 276-88
Studies on a second and third ring cyclization in anthracycline biosynthesis.
Hautala A, Torkkell S, Raty K, Kunnari T, Kantola J, Mantsala P, Hakala J, Ylihonko K
[PMID: 12715874]J Antibiot (Tokyo). 56 (2003) 143-53
Structure of the polyketide cyclase SnoaL reveals a novel mechanism for enzymatic aldol condensation.
Sultana A, Kallio P, Jansson A, Wang JS, Niemi J, Mantsala P, Schneider G
[PMID: 15071504]EMBO J. 23 (2004) 1911-21
Crystal structure of the polyketide cyclase AknH with bound substrate and product analogue: implications for catalytic mechanism and product stereoselectivity.
Kallio P, Sultana A, Niemi J, Mantsala P, Schneider G
[PMID: 16414075]J Mol Biol. 357 (2006) 210-20
Crystal structures of SnoaL2 and AclR: two putative hydroxylases in the biosynthesis of aromatic polyketide antibiotics.
Beinker P, Lohkamp B, Peltonen T, Niemi J, Mantsala P, Schneider G
[PMID: 16650858]J Mol Biol. 359 (2006) 728-40
Expression, purification and crystallization of the cofactor-independent monooxygenase SnoaB from the nogalamycin biosynthetic pathway.
Koskiniemi H, Grocholski T, Schneider G, Niemi J
[PMID: 19255477]Acta Crystallogr Sect F Struct Biol Cryst Commun. 65 (2009) 256-9
Crystal structure of the cofactor-independent monooxygenase SnoaB from Streptomyces nogalater: implications for the reaction mechanism.
Grocholski T, Koskiniemi H, Lindqvist Y, Mantsala P, Niemi J, Schneider G
[PMID: 20052967]Biochemistry. 49 (2010) 934-44
Identification of late-stage glycosylation steps in the biosynthetic pathway of the anthracycline nogalamycin.
Siitonen V, Claesson M, Patrikainen P, Aromaa M, Mantsala P, Schneider G, Metsa-Ketela M
[PMID: 22120896]Chembiochem. 13 (2012) 120-8
SnoaW/SnoaL2: a different two-component monooxygenase.
Bechthold A, Yan X
[PMID: 22633406]Chem Biol. 19 (2012) 549-51
Discovery of a two-component monooxygenase SnoaW/SnoaL2 involved in nogalamycin biosynthesis.
Siitonen V, Blauenburg B, Kallio P, Mantsala P, Metsa-Ketela M
[PMID: 22633415]Chem Biol. 19 (2012) 638-46
Crystal structure of the glycosyltransferase SnogD from the biosynthetic pathway of nogalamycin in Streptomyces nogalater.
Claesson M, Siitonen V, Dobritzsch D, Metsa-Ketela M, Schneider G
[PMID: 22804797]FEBS J. 279 (2012) 3251-63
Divergent non-heme iron enzymes in the nogalamycin biosynthetic pathway.
Siitonen V, Selvaraj B, Niiranen L, Lindqvist Y, Schneider G, Metsa-Ketela M
[PMID: 27114534]Proc Natl Acad Sci U S A. 113 (2016) 5251-6
Monooxygenase Substrates Mimic Flavin to Catalyze Cofactorless Oxygenations.
Machovina MM, Usselman RJ, DuBois JL
[PMID: 27307041]J Biol Chem. 291 (2016) 17816-28

close this sectionData download

Compound nameGenomic
nucleotide
sequence
Nucleotide
sequences of the
coding regions
Translation of the
coding sequences
List of genes/ORFsGBK
Nogalamycin
Genomic nucleotide sequence
49 KB
Nucleotide sequences of the coding regions
14 KB
Translation of the coding sequences
10 KB
List of genes/ORFs
2 KB

 

 
GenBank format
99 KB
AF323753
Genomic nucleotide sequence
13 KB
Nucleotide sequences of the coding regions
10 KB
Translation of the coding sequences
4 KB
List of genes/ORFs
1 KB

 

 

 
AF187532
Genomic nucleotide sequence
16 KB
Nucleotide sequences of the coding regions
16 KB
Translation of the coding sequences
6 KB
List of genes/ORFs
3 KB

 

 

 
AJ224512
Genomic nucleotide sequence
20 KB
Nucleotide sequences of the coding regions
18 KB
Translation of the coding sequences
7 KB
List of genes/ORFs
2 KB

 

 

 

close this sectionHistory

  • 2016-12-27[Update]
  • 2013-01-16[Update]
  • 2012-10-02[Release]