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Literature summary for 1.13.11.45 extracted from

  • Oliw, E.H.
    Factors influencing the rearrangement of bis-allylic hydroperoxides by manganese lipoxygenase (2008), J. Lipid Res., 49, 420-428.
    View publication on PubMed

Cloned(Commentary)

Cloned (Comment) Organism
expression in Pichia pastoris Gaeumannomyces graminis

Protein Variants

Protein Variants Comment Organism
G316A site-directed mutagenesis, the mutant changes the the position of lipoxygenation toward the carboxyl group of 20:2n-6 and 20:3n-3 and prevents the bis-allylic hydroperoxide of 20:3n-3 but not of 20:2n-6to interact with the catalytic metall Gaeumannomyces graminis
N466L site-directed mutagenesis, the mutation hardly affects the bis-allylic hydroperoxide rearrangement Gaeumannomyces graminis
S469A site-directed mutagenesis, the mutation hardly affects the bis-allylic hydroperoxide rearrangement, the mutant shows the same substrate profile as the wild-type enzyme Gaeumannomyces graminis

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.0024
-
linoleate pH 7.5, 18:3n-3 substrate Gaeumannomyces graminis

Localization

Localization Comment Organism GeneOntology No. Textmining
extracellular secretion Gaeumannomyces graminis
-
-

Metals/Ions

Metals/Ions Comment Organism Structure
Mn2+ required for activity Gaeumannomyces graminis
additional information no activity with Fe3+ Gaeumannomyces graminis

Organism

Organism UniProt Comment Textmining
Gaeumannomyces graminis
-
take-all fungus
-

Reaction

Reaction Comment Organism Reaction ID
linoleate + O2 = (9Z,12Z)-(11S)-11-hydroperoxyoctadeca-9,12-dienoate reaction mechanism, tail-first model with rearrangement at C13 at the end of lipoxygenation, influenced by double bond configuration and the chain length of fatty acids, overview Gaeumannomyces graminis

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(11Z,14Z)-eicosadienoic acid + O2
-
Gaeumannomyces graminis 15-hydroxyperoxy-(9Z,11E)-eicosadienoic acid
-
?
(11Z,14Z,17Z)-eicosa-11,14,17-trienoic acid + O2 via 11-hydroperoxyoctadecadienoic acid, 13-hydroperoxyoctadecadienoic acid and 15-hydroperoxyoctadecadienoic acid Gaeumannomyces graminis 15-hydroxyperoxy-11Z,13E,17Z-eicosatrienoic acid
-
?
(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid + O2 oxidation at the n-3 position Gaeumannomyces graminis ?
-
?
1-linoleyl-lyso-glycerophosphatidylcholine + O2 via formation of the 13-hydroxyperoxy metabolite Gaeumannomyces graminis 11-hydroxyoctadecanoic acid + 13-hydroxyoctadecanoic acid
-
?
11-hydroperoxyoctadecadienoic acid + O2
-
Gaeumannomyces graminis 11,18-dihydroxy-12E,14Z,16E-eicosatrienoic acid two diastereoisomers ?
alpha-linolenic acid + O2
-
Gaeumannomyces graminis (13R)-hydroperoxy octadecadienoic acid + 9-hydroperoxyoctadecadienoic acid
-
?
linoleate + O2
-
Gaeumannomyces graminis (9Z,12Z)-(11S)-11-hydroperoxyoctadeca-9,12-dienoate
-
?
linoleic acid + O2
-
Gaeumannomyces graminis ?
-
?
additional information the enzyme catalyzes the rearrangement of bis-allylic S-hydroxyperoxides to allylic R-hydroperoxides, and the oxygenation of 18:2n-6 by suprafacial hydrogen abstraction at C11 and O2 insertion at the bis-allylic position C11 and, with double bond migation, at the allylic position C13, overview, 20:4n-6 is a poor substrate, substrate specificities of wild-type and mutant enzymes, overview Gaeumannomyces graminis ?
-
?

Synonyms

Synonyms Comment Organism
manganese lipoxygenase
-
Gaeumannomyces graminis
Mn-LOX
-
Gaeumannomyces graminis

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
40
-
linoleate pH 7.5, 18:3n-3 substrate Gaeumannomyces graminis

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.5
-
assay at Gaeumannomyces graminis