KEGG ORTHOLOGY: K15943

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
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

Other DBs

RN:	R06676 R06681 R09328

Genes

MAU:	Micau_3999

MIL:

ML5_4422

AG:	AAA99000(dnrD) AAB16937(dauD) AAF01813(snoaL) AAF70112(aknH)

Reference

PMID:10639368

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

[ag:AAF01813]

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

[ag:AAA99000]

All links

Ontology (2)   
   KEGG BRITE (2)   
Pathway (7)   
   KEGG PATHWAY (6)   
   KEGG MODULE (1)   
Chemical reaction (7)   
   KEGG ENZYME (2)   
   KEGG REACTION (3)   
   KEGG RCLASS (2)   
Gene (7)   
   KEGG GENES (6)   
   OC (1)   
Protein sequence (8)   
   UniProt (5)   
   SWISS-PROT (3)   
Literature (2)   
   PubMed (2)   
All databases (33)   

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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

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

[ag:AAB16937]

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

[ag:AAA99000]

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

[ag:AAF70112]

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

REACTION: R06681

Entry

R06681 Reaction

Name

aklaviketone lyase (ring-opening);
methyl aklanonate cyclase

Definition

Methyl aklanonate <=> Aklaviketone

Equation

C12422 <=> C12423

Reaction class

RC02684

C12422_C12423

Enzyme

5.5.1.23

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 (7)   
   KEGG ORTHOLOGY (1)   
   KEGG GENES (6)   
All databases (19)   

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