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Literature summary for 4.2.1.92 extracted from

  • Hoffmann, I.; Oliw, E.H.
    Discovery of a linoleate 9S-dioxygenase and an allene oxide synthase in a fusion protein of Fusarium oxysporum (2013), J. Lipid Res., 54, 3471-3480.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

Cloned (Comment) Organism
gene FOXB_01332, phylogenetic tree, expression of wild-type and mutant enzymes Fusarium oxysporum

Protein Variants

Protein Variants Comment Organism
E946V site-directed mutagenesis, mutant Glu946Val oxidized 18:2n-6 as the native enzyme with formation of the alpha-ketol as the main product after 30 min Fusarium oxysporum
F416W site-directed mutagenesis, the catalytic residue mutant shows an unaltered product profile compared to the wild-type enzyme Fusarium oxysporum
N921V site-directed mutagenesis, the mutant shows activity similar to the wild-type enzyme Fusarium oxysporum
S949A site-directed mutagenesis, the mutant also forms alpha-ketol like the native enzyme Fusarium oxysporum

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid Fusarium oxysporum recombinant FOXB_01332 oxidizes 18:2n-6 to (9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid by hydrogen abstraction and antarafacial insertion of molecular oxygen and sequentially to an allene oxide, (9S,10)-epoxy-(10Z,12Z)-octadecadienoic acid, which gives nonenzymatic hydrolysis products alpha- and gamma-ketols (9S,10)-epoxy-(10Z,12Z)-octadecadienoic acid + H2O
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?
(9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid Fusarium oxysporum Fo5176 recombinant FOXB_01332 oxidizes 18:2n-6 to (9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid by hydrogen abstraction and antarafacial insertion of molecular oxygen and sequentially to an allene oxide, (9S,10)-epoxy-(10Z,12Z)-octadecadienoic acid, which gives nonenzymatic hydrolysis products alpha- and gamma-ketols (9S,10)-epoxy-(10Z,12Z)-octadecadienoic acid + H2O
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?
additional information Fusarium oxysporum FOXB_01332 is a linoleate 9-dioxygenase with homology to animal heme peroxidases and a 9-dioxygenase-allene oxide synthase fusion protein ?
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?
additional information Fusarium oxysporum Fo5176 FOXB_01332 is a linoleate 9-dioxygenase with homology to animal heme peroxidases and a 9-dioxygenase-allene oxide synthase fusion protein ?
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?

Organism

Organism UniProt Comment Textmining
Fusarium oxysporum F9F4K7 gene FOXB_01332
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Fusarium oxysporum Fo5176 F9F4K7 gene FOXB_01332
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid recombinant FOXB_01332 oxidizes 18:2n-6 to (9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid by hydrogen abstraction and antarafacial insertion of molecular oxygen and sequentially to an allene oxide, (9S,10)-epoxy-(10Z,12Z)-octadecadienoic acid, which gives nonenzymatic hydrolysis products alpha- and gamma-ketols Fusarium oxysporum (9S,10)-epoxy-(10Z,12Z)-octadecadienoic acid + H2O
-
?
(9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid recombinant FOXB_01332 oxidizes 18:2n-6 to (9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid by hydrogen abstraction and antarafacial insertion of molecular oxygen and sequentially to an allene oxide, (9S,10)-epoxy-(10Z,12Z)-octadecadienoic acid, which gives nonenzymatic hydrolysis products alpha- and gamma-ketols Fusarium oxysporum Fo5176 (9S,10)-epoxy-(10Z,12Z)-octadecadienoic acid + H2O
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?
(9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid recombinant FOXB_01332 oxidizes 18:2n-6 to (9S)-hydroperoxy-10(E),12(Z)-octadecadienoic acid by hydrogen abstraction and antarafacial insertion of molecular oxygen and sequentially to an allene oxide, (90S)-(10)-epoxy-10,12(Z)-octadecadienoic acid, which gives nonenzymatic hydrolysis products alpha- and gamma-ketols Fusarium oxysporum (9S,10)-10-epoxy-(10Z,12Z)-octadecadienoic acid + H2O
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?
(9S)-hydroperoxy-(10E,12Z,15Z)-octadecatrienoic acid
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Fusarium oxysporum (9S,10)-epoxy-(10Z,12Z,15Z)-octadecatrienoic acid + H2O
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?
(9Z,11E,13R)-13-hydroperoxyoctadeca-9,11-dienoic acid
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Fusarium oxysporum 11-hydroxy-12(13)-epoxy-octadecadienoic acid + 9-hydroxy-12(13)-epoxy-octadecadienoic acid + H2O
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?
(9Z,11E,13R)-13-hydroperoxyoctadeca-9,11-dienoic acid
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Fusarium oxysporum Fo5176 11-hydroxy-12(13)-epoxy-octadecadienoic acid + 9-hydroxy-12(13)-epoxy-octadecadienoic acid + H2O
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?
13-hydroperoxy-(10E,12Z)-octadecadienoic acid
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Fusarium oxysporum 11-hydroxy-12(13)-epoxy-octadecadienoic acid + 9-hydroxy-12(13)-epoxy-octadecadienoic acid + H2O
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?
13-hydroperoxy-(10E,12Z)-octadecadienoic acid
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Fusarium oxysporum Fo5176 11-hydroxy-12(13)-epoxy-octadecadienoic acid + 9-hydroxy-12(13)-epoxy-octadecadienoic acid + H2O
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?
additional information FOXB_01332 is a linoleate 9-dioxygenase with homology to animal heme peroxidases and a 9-dioxygenase-allene oxide synthase fusion protein Fusarium oxysporum ?
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?
additional information (9S)-dioxygenase-allene oxide synthase converts 9S-hydroperoxyoctadecadienoic acid to alpha- and gamma-ketols, likely formed by hydrolysis of (9S,10)-(10)-epoxy-(10Z,12Z)-octadecadienoic acid, along with small amounts of epoxy alcohols. The (9R)-hydroperoxyoctadecadienoic acid preparation contains a few percent (9S)-hydroperoxyoctadecadienoic acid, and only the latter is apparently transformed to an alpha-ketol by (9S)-dioxygenase-allene oxide synthase. (13S)-hydroperoxyoctadecadienoic acid, (13S)-hydroxy-(10E,12Z,15Z)-octadecatrienoicacid, (13R)-hydroperoxyoctadecadienoic acid, and (13R)-hydroxy-(10E,12Z,15Z)-octadecatrienoicacid are not transformed to detectable amounts of allene oxides/alpha-ketols, but variable amounts of epoxy alcohols accumulate, mass spectrometric analysis of products, substrate specificity, overview Fusarium oxysporum ?
-
?
additional information FOXB_01332 is a linoleate 9-dioxygenase with homology to animal heme peroxidases and a 9-dioxygenase-allene oxide synthase fusion protein Fusarium oxysporum Fo5176 ?
-
?
additional information (9S)-dioxygenase-allene oxide synthase converts 9S-hydroperoxyoctadecadienoic acid to alpha- and gamma-ketols, likely formed by hydrolysis of (9S,10)-(10)-epoxy-(10Z,12Z)-octadecadienoic acid, along with small amounts of epoxy alcohols. The (9R)-hydroperoxyoctadecadienoic acid preparation contains a few percent (9S)-hydroperoxyoctadecadienoic acid, and only the latter is apparently transformed to an alpha-ketol by (9S)-dioxygenase-allene oxide synthase. (13S)-hydroperoxyoctadecadienoic acid, (13S)-hydroxy-(10E,12Z,15Z)-octadecatrienoicacid, (13R)-hydroperoxyoctadecadienoic acid, and (13R)-hydroxy-(10E,12Z,15Z)-octadecatrienoicacid are not transformed to detectable amounts of allene oxides/alpha-ketols, but variable amounts of epoxy alcohols accumulate, mass spectrometric analysis of products, substrate specificity, overview Fusarium oxysporum Fo5176 ?
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?

Synonyms

Synonyms Comment Organism
9S-DOX-AOS
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Fusarium oxysporum
FOXB_01332
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Fusarium oxysporum

General Information

General Information Comment Organism
evolution FOXB_01332 is a linoleate 9-DOX with homology to animal heme peroxidases and a 9-dioxygenase-allene oxide synthase fusion protein. The conserved Tyr-(His/Arg)-Trp-His motif contains a Phe instead of the catalytic Tyr residue, which is oxidized by the heme to a radical that performs the hydrogen abstraction of LDS and COX, the replacement of Phe 416 with Trp does not affect the product profile of FOXB_01332 Fusarium oxysporum
additional information the acid-alcohol pair Glu946-Ser949 lacks catalytic importance for the allene oxide synthase activity Fusarium oxysporum