KEGG ENZYME: 5.4.4.5

ENZYME: 5.4.4.5

Entry

EC 5.4.4.5                  Enzyme

Name

9,12-octadecadienoate 8-hydroperoxide 8R-isomerase;
5,8-LDS (bifunctional enzyme);
5,8-linoleate diol synthase (bifunctional enzyme);
8-hydroperoxide isomerase;
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate mutase ((5S,8R,9Z,12Z)-5,8-dihydroxy-9,12-octadecadienoate-forming);
PpoA

Class

Isomerases;
Intramolecular transferases;
Transferring hydroxy groups

Sysname

(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate hydroxymutase [(5S,8R,9Z,12Z)-5,8-dihydroxyoctadeca-9,12-dienoate-forming]

Reaction(IUBMB)

(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate = (5S,8R,9Z,12Z)-5,8-dihydroxyoctadeca-9,12-dienoate [RN:R09905]

Reaction(KEGG)

R09905

Substrate

(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate [CPD:C14831]

Product

(5S,8R,9Z,12Z)-5,8-dihydroxyoctadeca-9,12-dienoate [CPD:C20186]

Comment

The enzyme contains heme [3]. The bifunctional enzyme from Aspergillus nidulans uses different heme domains to catalyse two separate reactions. Linoleic acid is oxidized within the N-terminal heme peroxidase domain to (8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate (cf. EC 1.13.11.60, linoleate 8R-lipoxygenase), which is subsequently isomerized to (5S,8R,9Z,12Z)-5,8-dihydroxyoctadeca-9,12-dienoate within the C-terminal P-450 heme thiolate domain [3].

History

EC 5.4.4.5 created 2011

Pathway

ec00591

Linoleic acid metabolism

Orthology

K17863

linoleate 8R-lipoxygenase / 9,12-octadecadienoate 8-hydroperoxide 8R-isomerase

Genes

PBEL:

QC761_104690

PPSD:

QC762_104690

PPSP:

QC763_104690

PPSA:

QC764_104690

PPEI:

PpBr36_02801

PGRI:

PgNI_01911

CHIG:

CH63R_03596

ANI:	ANIA_01967

AFM:	AFUA_4G10770

ACT:	ACLA_049940

NFI:	NFIA_105320

AOR:	AO090003001138

ANG:	An04g05880

AFV:	AFLA_000529

ALUC:

AKAW2_51557A

ACHE:

ACHE_10811S

APUU:

APUU_21090S

PCS:	N7525_005537

PDP:	PDIP_33150

POU:	POX_d06058

TMF:	EYB26_002074

CIM:	CIMG_01479

CPW:	CPC735_049620

URE:	UREG_05116

PBL:	PAAG_02631

PBN:	PADG_01651

ABE:

ARB_02272

TVE:

TRV_04981

AJE:	HCAG_01669

RSX:	RhiXN_10303

E1B28_012947

PTRC:

PtA15_12A250

PSTR:

Pst134EA_022959

» show all

Reference

1 [PMID:21130068]

Authors

Hoffmann I, Jerneren F, Garscha U, Oliw EH

Title

Expression of 5,8-LDS of Aspergillus fumigatus and its dioxygenase domain. A comparison with 7,8-LDS, 10-dioxygenase, and cyclooxygenase.

Journal

Arch Biochem Biophys 506:216-22 (2011)
DOI:10.1016/j.abb.2010.11.022

Sequence

[afm:AFUA_4G10770]

Reference

2 [PMID:20045744]

Authors

Jerneren F, Garscha U, Hoffmann I, Hamberg M, Oliw EH

Title

Reaction mechanism of 5,8-linoleate diol synthase, 10R-dioxygenase, and 8,11-hydroperoxide isomerase of Aspergillus clavatus.

Journal

Biochim Biophys Acta 1801:503-7 (2010)
DOI:10.1016/j.bbalip.2009.12.012

Reference

3 [PMID:19286665]

Authors

Brodhun F, Gobel C, Hornung E, Feussner I

Title

Identification of PpoA from Aspergillus nidulans as a fusion protein of a fatty acid heme dioxygenase/peroxidase and a cytochrome P450.

Journal

J Biol Chem 284:11792-805 (2009)
DOI:10.1074/jbc.M809152200

Sequence

[ani:ANIA_01967]

Other DBs

ExplorEnz - The Enzyme Database:

5.4.4.5

IUBMB Enzyme Nomenclature:

5.4.4.5

ExPASy - ENZYME nomenclature database:

5.4.4.5

BRENDA, the Enzyme Database:

5.4.4.5

DBGET integrated database retrieval system