Information on EC 1.1.13.B29 - fatty acid omega2/3-hydroxyase

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The expected taxonomic range for this enzyme is: Homo sapiens

EC NUMBER
COMMENTARY hide
1.1.13.B29
preliminary BRENDA-supplied EC number
RECOMMENDED NAME
GeneOntology No.
fatty acid omega2/3-hydroxyase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate + NADPH + H+ + O2 = (4Z,7Z,10Z,13Z,16Z)-19,20-epoxydocosa-4,7,10,13,16-pentaenoate + NADP+ + H2O
show the reaction diagram
(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate + NADPH + H+ + O2 = (4Z,7Z,10Z,16Z,19Z)-13,14-epoxydocosa-4,7,10,16,19-pentaenoate + NADP+ + H2O
show the reaction diagram
(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate + NADPH + H+ + O2 = (4Z,7Z,13Z,16Z,19Z)-10,11-epoxydocosa-4,7,13,16,19-pentaenoate + NADP+ + H2O
show the reaction diagram
SYSTEMATIC NAME
IUBMB Comments
fatty acid,NADPH:oxygen oxidoreductase omega2/3-hydroxylating
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
UniProt
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoate + NADPH + H+ + O2
(4Z,7Z,10Z,13Z,16Z)-20-hydroxydocosa-4,7,10,13,16-pentaenoate
show the reaction diagram
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main product, plus minor amounts of 21-hydroxy-4,7,10,13,16-(Z)-docosapentaenoic acid, no significant formation of dihydroxycompounds
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?
(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate + NADPH + H+ + O2
(4Z,7Z,10Z,13Z,16Z)-19,20-epoxydocosa-4,7,10,13,16-pentaenoate + NADP+ + H2O
show the reaction diagram
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formation of 19,20-epoxydocosapentaenoic acid, 16,17-epoxydocosahexaenoic acid, 13,14-epoxydocosahexaenoic acid, and 10,11-epoxydocosahexaenoic acid, no significant formation of 21-hydroxy- or 22-hydroxydocosahexaenoic acid. Reaction is catalyzed by both isoforms CYP4F8 and CYP4F12
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?
(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate + NADPH + H+ + O2
(4Z,7Z,10Z,16Z,19Z)-13,14-epoxydocosa-4,7,10,16,19-pentaenoate + NADP+ + H2O
show the reaction diagram
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formation of 19,20-epoxydocosapentaenoic acid, 16,17-epoxydocosahexaenoic acid, 13,14-epoxydocosahexaenoic acid, and 10,11-epoxydocosahexaenoic acid, no significant formation of 21-hydroxy- or 22-hydroxydocosahexaenoic acid. Reaction is catalyzed by both isoforms CYP4F8 and CYP4F12
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?
(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate + NADPH + H+ + O2
(4Z,7Z,13Z,16Z,19Z)-10,11-epoxydocosa-4,7,13,16,19-pentaenoate + NADP+ + H2O
show the reaction diagram
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formation of 19,20-epoxydocosapentaenoic acid, 16,17-epoxydocosahexaenoic acid, 13,14-epoxydocosahexaenoic acid, and 10,11-epoxydocosahexaenoic acid, no significant formation of 21-hydroxy- or 22-hydroxydocosahexaenoic acid. Reaction is catalyzed by both isoforms CYP4F8 and CYP4F12
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?
(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate + NADPH + H+ + O2
(7Z,10Z,13Z,16Z)-19,20-epoxydocosa-7,10,13,16-tetraenoate + NADP+ + H2O
show the reaction diagram
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formation of 19,20-epoxydocosatetraenoic acid, 16,17-epoxydocosatetraenoic acid, 13,14-epoxydocosatetraenoic acid, and 10,11-epoxydocosatetraenoic acid, no formation of 21-hydroxy- or 22-hydroxydocosapentaenoic acid
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?
(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate + NADPH + H+ + O2
(7Z,10Z,13Z,19Z)-16,17-epoxydocosa-7,10,13,19-tetraenoate + NADP+ + H2O
show the reaction diagram
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formation of 19,20-epoxydocosapentaenoic acid, 16,17-epoxydocosapentaenoic acid, 13,14-epoxydocosapentaenoic acid, and 10,11-epoxydocosapentaenoic acid, no formation of 21-hydroxy- or 22-hydroxydocosapentaenoic acid
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?
(7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate + NADPH + H+ + O2
(7Z,13Z,16Z,19Z)-10,11-epoxydocosa-7,13,16,19-tetraenoate + NADP+ + H2O
show the reaction diagram
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formation of 19,20-epoxydocosapentaenoic acid, 16,17-epoxydocosapentaenoic acid, 13,14-epoxydocosapentaenoic acid, and 10,11-epoxydocosapentaenoic acid, no formation of 21-hydroxy- or 22-hydroxydocosapentaenoic acid
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?
arachidonic acid + NADPH + H+ + O2
18-hydroxyarachidonic acid + NADP+ + H2O
show the reaction diagram
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hydroxylation at C-18
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?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.4
assay at; assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
assay at; assay at
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli, Saccharomyces cerevisiae; expression in Escherichia coli, Saccharomyces cerevisiae
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
G328E
mutant oxidizes prostaglandin H2 analogs U-51605 and U-44069 as recombinant CYP4F8, but the hydroxylation of arachidonic acid is shifted from C-18 to C-19
Y125F
missense mutation in substrate recognition site-1, occuring naturally in low frequency. The variant oxidizes prostaglandin H2 analogs U-51605, i.e. 9,11-diazo-prostadienoic acid, and U-44069, i.e. 9alpha,11alpha-epoxymethano-prostaglandin H2 in omega2 and omega3 position, but 4,7,10,13,16-(Z)-docosatetraenoic acid and 4,7,10,13,16-(Z)-docosapentaenoic acid are not oxidized
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
missense mutation Y125F in substrate recognition site-1 occurs naturally in low frequency. The variant oxidizes two prostaglandin H2 analogs U-51605 and U-44069, but 4,7,10,13,16-(Z)-docosatetraenoic acid and 4,7,10,13,16-(Z)-docosapentaenoic acid are not oxidized