KEGG   ORTHOLOGY: K15943Help
Entry
K15943                      KO                                     

Name
snoaL, dnrD, dauD, aknH
Definition
nogalonic acid methyl ester cyclase / aklanonic acid methyl ester cyclase [EC:5.5.1.26 5.5.1.23]
Pathway
ko01057  Biosynthesis of type II polyketide products
ko01100  Metabolic pathways
ko01130  Biosynthesis of antibiotics
Module
M00781  Nogalavinone/aklavinone biosynthesis, deoxynogalonate/deoxyaklanonate => nogalavinone/aklavinone
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09109 Metabolism of terpenoids and polyketides
   01057 Biosynthesis of type II polyketide products
    K15943  snoaL, dnrD, dauD, aknH; nogalonic acid methyl ester cyclase / aklanonic acid methyl ester cyclase
Enzymes [BR:ko01000]
 5. Isomerases
  5.5  Intramolecular lyases
   5.5.1  Intramolecular lyases (only sub-subclass identified to date)
    5.5.1.23  aklanonic acid methyl ester cyclase
     K15943  snoaL, dnrD, dauD, aknH; nogalonic acid methyl ester cyclase / aklanonic acid methyl ester cyclase
    5.5.1.26  nogalonic acid methyl ester cyclase
     K15943  snoaL, dnrD, dauD, aknH; nogalonic acid methyl ester cyclase / aklanonic acid methyl ester cyclase
BRITE hierarchy
Other DBs
RN: R06676 R06681 R09328
Genes
MAU: Micau_3999
MIL: ML5_4422
AG: AAA99000(dnrD) AAB16937(dauD) AAF01813(snoaL) AAF70112(aknH)
TaxonomyKoalaUniProt
Reference
  Authors
Torkkell S, Kunnari T, Palmu K, Hakala J, Mantsala P, Ylihonko K
  Title
Identification of a cyclase gene dictating the C-9 stereochemistry of anthracyclines from Streptomyces nogalater.
  Journal
Antimicrob Agents Chemother 44:396-9 (2000)
DOI:10.1128/AAC.44.2.396-399.2000
  Sequence
Reference
PMID:7601857
  Authors
Madduri K, Hutchinson CR
  Title
Functional characterization and transcriptional analysis of a gene cluster governing early and late steps in daunorubicin biosynthesis in Streptomyces peucetius.
  Journal
J Bacteriol 177:3879-84 (1995)
DOI:10.1128/JB.177.13.3879-3884.1995
  Sequence

KEGG   ENZYME: 5.5.1.23Help
Entry
EC 5.5.1.23                 Enzyme                                 

Name
aklanonic acid methyl ester cyclase;
dauD (gene name);
aknH (gene name);
dnrD (gene name);
methyl aklanonate cyclase;
methyl aklanonate-aklaviketone isomerase (cyclizing);
aklaviketone lyase (decyclizing)
Class
Isomerases;
Intramolecular lyases;
Intramolecular lyases (only sub-subclass identified to date)
BRITE hierarchy
Sysname
aklaviketone lyase (ring-opening)
Reaction(IUBMB)
aklaviketone = methyl aklanonate [RN:R06681]
Reaction(KEGG)
R06681;
(other) R06676
Show
Substrate
aklaviketone [CPD:C12423]
Product
methyl aklanonate [CPD:C12422]
Comment
The enzyme is involved in the biosynthesis of aklaviketone, an intermediate in the biosynthetic pathways leading to formation of several anthracycline antibiotics, including aclacinomycin, daunorubicin and doxorubicin.
History
EC 5.5.1.23 created 2013, modified 2014
Pathway
ec01057  Biosynthesis of type II polyketide products
ec01100  Metabolic pathways
ec01130  Biosynthesis of antibiotics
Orthology
K15943  nogalonic acid methyl ester cyclase / aklanonic acid methyl ester cyclase
Genes
MAU: Micau_3999
MIL: ML5_4422
Taxonomy
Reference
1  [PMID:7836284]
  Authors
Dickens ML, Ye J, Strohl WR.
  Title
Analysis of clustered genes encoding both early and late steps in daunomycin biosynthesis by Streptomyces sp. strain C5.
  Journal
J Bacteriol 177:536-43 (1995)
DOI:10.1128/JB.177.3.536-543.1995
  Sequence
Reference
2  [PMID:10200167]
  Authors
Kendrew SG, Katayama K, Deutsch E, Madduri K, Hutchinson CR
  Title
DnrD cyclase involved in the biosynthesis of doxorubicin: purification and characterization of the recombinant enzyme.
  Journal
Biochemistry 38:4794-9 (1999)
DOI:10.1021/bi9827924
  Sequence
Reference
3  [PMID:16414075]
  Authors
Kallio P, Sultana A, Niemi J, Mantsala P, Schneider G.
  Title
Crystal structure of the polyketide cyclase AknH with bound substrate and product analogue: implications for catalytic mechanism and product stereoselectivity.
  Journal
J Mol Biol 357:210-20 (2006)
DOI:10.1016/j.jmb.2005.12.064
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 5.5.1.23
IUBMB Enzyme Nomenclature: 5.5.1.23
ExPASy - ENZYME nomenclature database: 5.5.1.23
BRENDA, the Enzyme Database: 5.5.1.23

KEGG   REACTION: R06676Help
Entry
R06676                      Reaction                               

Name
auraviketone lyase (decyclizing)
Definition
Methyl nogalonate <=> Auraviketone
Equation
Comment
cyclase, aknH (acmA)
Reaction class
RC01671  C12415_C12417
Enzyme
Pathway
rn01057  Biosynthesis of type II polyketide products
rn01130  Biosynthesis of antibiotics
Orthology
K15943  nogalonic acid methyl ester cyclase / aklanonic acid methyl ester cyclase [EC:5.5.1.26 5.5.1.23]

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