KEGG ORTHOLOGY: K15943

ORTHOLOGY: K15943

Entry

K15943                      KO

Symbol

snoaL, dnrD, dauD, aknH

Name

nogalonic acid methyl ester cyclase / aklanonic acid methyl ester cyclase [EC:5.5.1.26 5.5.1.23]

Pathway

map01057

Biosynthesis of type II polyketide products

map01100

Metabolic pathways

map01110

Biosynthesis of secondary metabolites

Module

M00781

Nogalavinone/aklavinone biosynthesis, deoxynogalonate/deoxyaklanonate => nogalavinone/aklavinone

Reaction

R06676

auraviketone lyase (decyclizing)

R06681

aklaviketone lyase (ring-opening)

R09328

nogalaviketone lyase (ring-opening)

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

Genes

SPRI:

SPRI_0207 SPRI_7146

STIR:

DDW44_27900

SKA:	CP970_39840

SGAL:

CP966_29100

SCIN:

CP977_27950

STSU:

B7R87_22025

SCHA:

CP983_03560 CP983_03585

SCOE:

CP976_32890

SPEU:

CGZ69_24290

SXN:	IAG42_36860

SDD:	D9753_08650

SJN:	RI060_18395

SHAU:

K9S39_40665

SKG:	KJK29_16195

STVB:

OH133_10920

TALX:

FOF52_07395

PMAD:

BAY61_07675

MAU:	Micau_3999

MIL:

ML5_4422

MFEU:

H1D33_25685

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

» show all

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

Gene (1)   
   OC (1)   
All databases (1)   

Download RDF

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

SPRI:

SPRI_0207 SPRI_7146

STIR:

DDW44_27900

SKA:	CP970_39840

SGAL:

CP966_29100

SCIN:

CP977_27950

STSU:

B7R87_22025

SCHA:

CP983_03560 CP983_03585

SCOE:

CP976_32890

SPEU:

CGZ69_24290

SXN:	IAG42_36860

SDD:	D9753_08650

SJN:	RI060_18395

SHAU:

K9S39_40665

SKG:	KJK29_16195

STVB:

OH133_10920

TALX:

FOF52_07395

PMAD:

BAY61_07675

MAU:	Micau_3999

MIL:

ML5_4422

MFEU:

H1D33_25685

» show all

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

All links

Protein sequence (25)   
   UniProt (22)   
   SWISS-PROT (3)   
DNA sequence (12)   
   GenBank (6)   
   EMBL (6)   
Protein domain (2)   
   InterPro (2)   
All databases (39)   

Download RDF

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

Brite

Enzymatic reactions [BR:br08201]
5. Isomerase reactions
  5.5  Intramolecular lyases
   5.5.1  Intramolecular lyases (only sub-subclass identified to date)
    5.5.1.23
     R06681  Methyl aklanonate <=> Aklaviketone

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

No link information was found.

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