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

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]

LinkDB

ENZYME: 5.5.1.26

Entry

EC 5.5.1.26                 Enzyme

Name

nogalonic acid methyl ester cyclase;
methyl nogalonate cyclase;
SnoaL (gene name);
methyl nogalonate lyase (cyclizing)

Class

Isomerases;
Intramolecular lyases;
Intramolecular lyases (only sub-subclass identified to date)

Sysname

nogalaviketone lyase (ring-opening)

Reaction(IUBMB)

nogalaviketone = methyl nogalonate [RN:R09328]

Reaction(KEGG)

R09328

Substrate

nogalaviketone [CPD:C18630]

Product

methyl nogalonate [CPD:C12415]

Comment

The enzyme, characterized from the bacterium Streptomyces nogalater, is involved in the biosynthesis of the aromatic polyketide nogalamycin.

History

EC 5.5.1.26 created 2015

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

TALX:

FOF52_07395

PMAD:

BAY61_07675

MAU:	Micau_3999

MIL:

ML5_4422

MFEU:

H1D33_25685

» show all

Reference

1 [PMID:15071504]

Authors

Sultana A, Kallio P, Jansson A, Wang JS, Niemi J, Mantsala P, Schneider G

Title

Structure of the polyketide cyclase SnoaL reveals a novel mechanism for enzymatic aldol condensation.

Journal

EMBO J 23:1911-21 (2004)
DOI:10.1038/sj.emboj.7600201

Sequence

[ag:AAF01813]

Reference

2 [PMID:15159574]

Authors

Sultana A, Kallio P, Jansson A, Niemi J, Mantsala P, Schneider G

Title

Crystallization and preliminary crystallographic data of SnoaL, a polyketide cyclase in nogalamycin biosynthesis.

Journal

Acta Crystallogr D Biol Crystallogr 60:1118-20 (2004)
DOI:10.1107/S090744490400705X

Other DBs

ExplorEnz - The Enzyme Database:

5.5.1.26

IUBMB Enzyme Nomenclature:

5.5.1.26

ExPASy - ENZYME nomenclature database:

5.5.1.26

BRENDA, the Enzyme Database:

5.5.1.26

LinkDB

REACTION: R09328

Entry

R09328                      Reaction

Name

nogalaviketone lyase (ring-opening);
methyl nogalonate cyclase

Definition

Methyl nogalonate <=> Nogalaviketone

Equation

C12415 <=> C18630

Reaction class

RC01671

C12415_C18630

Enzyme

5.5.1.26

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)
    5.5.1.26
     R09328  Methyl nogalonate <=> Nogalaviketone

Orthology

K15943

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

Other DBs

RHEA:

44359

LinkDB

DBGET integrated database retrieval system