KEGG ENZYME: 5.4.4.6

ENZYME: 5.4.4.6

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

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)

R07062

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

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

[ag:AAD49559]