Nogalamycin : Cluster information
Compound
Entry name | Nogalamycin |
---|---|
PKS Type | TypeII |
Starter Unit | acetyl-CoA |
Chain Length | 10 |
Sugar Unit | nogalamine nogalose |
Classification | Anthracycline |
Activity | Antibacterial Antitumor Toxic |
Composition | C39H49NO16 |
Original source
Organism | Streptomyces nogalater |
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Strain | ATCC 27451 (=NBRC 13445) |
Contig | AF323753 AF187532 AJ224512 |
PKS/NRPS Module
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Reference
- 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
Data download
History
- 2016-12-27[Update]
- 2013-01-16[Update]
- 2012-10-02[Release]