KEGG   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
ABE: ARB_02272
TVE: TRV_04981
PBL: PAAG_02631
PBN: PADG_01651
AJE: HCAG_01669
RSX: RhiXN_10303
MORE: E1B28_012947
PTRC: PtA15_12A250
PSTR: Pst134EA_022959
RIE: OCT59_013577
 » 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
LinkDB

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