KEGG   ORTHOLOGY: K15943
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
ko01110  Biosynthesis of secondary metabolites
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
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   01008 Polyketide biosynthesis proteins
    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
Polyketide biosynthesis proteins [BR:ko01008]
 Polyketide tailoring proteins
  Others
   K15943  snoaL, dnrD, dauD, aknH; nogalonic acid methyl ester cyclase / aklanonic acid methyl ester cyclase
Other DBs
RN: R06676 R06681 R09328
Genes
STIR: DDW44_27900
SKA: CP970_39840
SGAL: CP966_29100
SCIN: CP977_27950
STSU: B7R87_22025
SCHA: CP983_03560 CP983_03585
SCOE: CP976_32890
MAU: Micau_3999
MIL: ML5_4422
AG: AAA99000(dnrD) AAB16937(dauD) AAF01813(snoaL) AAF70112(aknH)
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

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Ontology (3)   
   KEGG BRITE (3)   
Pathway (7)   
   KEGG PATHWAY (6)   
   KEGG MODULE (1)   
Chemical reaction (7)   
   KEGG ENZYME (2)   
   KEGG REACTION (3)   
   KEGG RCLASS (2)   
Gene (15)   
   KEGG GENES (14)   
   OC (1)   
Literature (2)   
   PubMed (2)   
All databases (34)   

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KEGG   ENZYME: 5.5.1.23
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)
Sysname
aklaviketone lyase (ring-opening)
Reaction(IUBMB)
aklaviketone = methyl aklanonate [RN:R06681]
Reaction(KEGG)
R06681;
(other) R06676
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
ec01110  Biosynthesis of secondary metabolites
Orthology
K15943  nogalonic acid methyl ester cyclase / aklanonic acid methyl ester cyclase
Genes
STIR: DDW44_27900
SKA: CP970_39840
SGAL: CP966_29100
SCIN: CP977_27950
STSU: B7R87_22025
SCHA: CP983_03560 CP983_03585
SCOE: CP976_32890
MAU: Micau_3999
MIL: ML5_4422
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

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Pathway (7)   
   KEGG PATHWAY (6)   
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Chemical substance (4)   
   KEGG COMPOUND (4)   
Chemical reaction (4)   
   KEGG REACTION (2)   
   KEGG RCLASS (2)   
Gene (15)   
   KEGG ORTHOLOGY (1)   
   KEGG GENES (14)   
Protein sequence (24)   
   UniProt (21)   
   SWISS-PROT (3)   
DNA sequence (9)   
   GenBank (5)   
   EMBL (4)   
Protein domain (2)   
   InterPro (2)   
All databases (65)   

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KEGG   REACTION: R06681
Entry
R06681                      Reaction                               

Name
aklaviketone lyase (ring-opening);
methyl aklanonate cyclase
Definition
Methyl aklanonate <=> Aklaviketone
Equation
Reaction class
RC02684  C12422_C12423
Enzyme
Pathway
rn01057  Biosynthesis of type II polyketide products
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00781  Nogalavinone/aklavinone biosynthesis, deoxynogalonate/deoxyaklanonate => nogalavinone/aklavinone
Orthology
K15943  nogalonic acid methyl ester cyclase / aklanonic acid methyl ester cyclase [EC:5.5.1.26 5.5.1.23]
Other DBs
RHEA: 37882

  All links  
Ontology (1)   
   KEGG BRITE (1)   
Pathway (7)   
   KEGG PATHWAY (6)   
   KEGG MODULE (1)   
Chemical substance (2)   
   KEGG COMPOUND (2)   
Chemical reaction (2)   
   KEGG ENZYME (1)   
   KEGG RCLASS (1)   
Gene (15)   
   KEGG ORTHOLOGY (1)   
   KEGG GENES (14)   
All databases (27)   

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