KEGG   ENZYME: 5.4.4.6Help
Entry
EC 5.4.4.6                  Enzyme                                 

Name
9,12-octadecadienoate 8-hydroperoxide 8S-isomerase;
8-hydroperoxide isomerase (ambiguous);
(8R,9Z,12Z)-8-hydroperoxy-9,12-octadecadienoate mutase ((7S,8S,9Z,12Z)-7,8-dihydroxy-9,12-octadecadienoate-forming)
Class
Isomerases;
Intramolecular transferases;
Transferring hydroxy groups
BRITE hierarchy
Sysname
(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate hydroxymutase [(7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoate-forming]
Reaction(IUBMB)
(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate = (7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoate [RN:R07062]
Reaction(KEGG)
Substrate
(8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate [CPD:C14831]
Product
(7S,8S,9Z,12Z)-7,8-dihydroxyoctadeca-9,12-dienoate [CPD:C07354]
Comment
The enzyme contains heme. The bifunctional enzyme from Gaeumannomyces graminis catalyses the oxidation of linoleic acid to (8R,9Z,12Z)-8-hydroperoxyoctadeca-9,12-dienoate (cf. EC 1.13.11.60, linoleate 8R-lipoxygenase), which is then isomerized to (7S,8S,9Z,12Z)-5,8-dihydroxyoctadeca-9,12-dienoate [3].
History
EC 5.4.4.6 created 2011
Pathway
ec00591  Linoleic acid metabolism
Orthology
K17864  linoleate 8R-lipoxygenase / 9,12-octadecadienoate 8-hydroperoxide 8S-isomerase
Genes
PAN: PODANSg09720
MGR: MGG_13239
Taxonomy
Reference
1  [PMID:8117115]
  Authors
Hamberg M, Zhang LY, Brodowsky ID, Oliw EH.
  Title
Sequential oxygenation of linoleic acid in the fungus Gaeumannomyces graminis: stereochemistry of dioxygenase and hydroperoxide isomerase reactions.
  Journal
Arch Biochem Biophys 309:77-80 (1994)
DOI:10.1006/abbi.1994.1087
Reference
2  [PMID:9694817]
  Authors
Su C, Sahlin M, Oliw EH.
  Title
A protein radical and ferryl intermediates are generated by linoleate diol synthase, a ferric hemeprotein with dioxygenase and hydroperoxide isomerase activities.
  Journal
J Biol Chem 273:20744-51 (1998)
DOI:10.1074/jbc.273.33.20744
Reference
3  [PMID:8662736]
  Authors
Su C, Oliw EH.
  Title
Purification and characterization of linoleate 8-dioxygenase from the fungus Gaeumannomyces graminis as a novel hemoprotein.
  Journal
J Biol Chem 271:14112-8 (1996)
DOI:10.1074/jbc.271.24.14112
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 5.4.4.6
IUBMB Enzyme Nomenclature: 5.4.4.6
ExPASy - ENZYME nomenclature database: 5.4.4.6
BRENDA, the Enzyme Database: 5.4.4.6

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