Information on EC 4.2.1.B8 - etheroleic acid synthase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
4.2.1.B8
preliminary BRENDA-supplied EC number
RECOMMENDED NAME
GeneOntology No.
etheroleic acid synthase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate = (9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
show the reaction diagram
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SYSTEMATIC NAME
IUBMB Comments
(9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid synthase
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
two CYP74Q1 isoforms, gene CYP74Q1
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
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the enzyme belongs to the CYP74 family, phylogenetic tree
physiological function
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enzymes of the CYP74 family, including the divinyl ether synthase, play important roles in plant cell signalling and defence
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid
?
show the reaction diagram
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poor substrate
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?
(9S,10E,12Z,15Z)-13-hydroperoxy-10,12,15-octadecatrienoate
(9Z,11E)-12-[(1'Z,3'Z)-hexadienyloxy]-9,11-dodecadienoate
show the reaction diagram
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highly preferred substrate
i.e. (omega5Z)-etheroleic acid
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?
(9Z,11E,13R)-13-hydroperoxy-9,11-octadecadienoate
(9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
show the reaction diagram
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is utilized more slowly than (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
i.e. etheroleic acid
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?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
(9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + (9E,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
show the reaction diagram
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the S enantiomer is a much better substrate for the divinyl ether synthase compared to the R enantiomer. Incubation of (9Z,11E,13S)-[18O2]hydroperoxy-9,11-octadecadienoic acid leads to the formation of etheroleic acid which retains 18O in the ether oxygen. An intermediary role of an epoxyallylic cation in etheroleic acid biosynthesis is postulated
two isomers of etheroleic acid are isolated
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?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
(9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
show the reaction diagram
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
(9Z,11E)-12-[(1'Z)-hexenyloxy]-9,11-dodecadienoic acid
show the reaction diagram
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i.e. (omega5Z)-etherolenic acid
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?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoate
(9Z,11E)-12-[(1E,3Z)-hexa-1,3-dien-1-yloxy]dodeca-9,11-dienoic acid + H2O
show the reaction diagram
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i.e. etherolenic acid
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?
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(9S,10E,12Z,15Z)-13-hydroperoxy-10,12,15-octadecatrienoate
(9Z,11E)-12-[(1'Z,3'Z)-hexadienyloxy]-9,11-dodecadienoate
show the reaction diagram
-
highly preferred substrate
i.e. (omega5Z)-etheroleic acid
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?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
(9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
show the reaction diagram
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i.e. etheroleic acid
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?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
(9Z,11E)-12-[(1'Z)-hexenyloxy]-9,11-dodecadienoic acid
show the reaction diagram
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i.e. (omega5Z)-etherolenic acid
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?
additional information
?
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preferred substrates of the enzyme are the 13-hydroperoxides of alpha-linolenic and linoleic acids, which are converted to the divinyl ether oxylipins (omega5Z)-etherolenic acid, (9Z,11E)-12-[(1?Z,3?Z)-hexadienyloxy]-9,11-dodecadienoic acid, and (omega5Z)-etheroleic acid, (9Z,11E)-12-[(1?Z)-hexenyloxy]-9,11-dodecadienoic acid, respectively, as revealed by the data of mass spectrometry, NMR and UV spectroscopy
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0976
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
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pH 7.5, 25°C
0.0431
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienate
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pH 7.5, 25°C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
67.7
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
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pH 7.5, 25°C
134
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienate
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pH 7.5, 25°C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0007
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
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pH 7.5, 25°C
0.0031
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienate
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pH 7.5, 25°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5
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assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
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assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
gene CYP74Q1, DNA and amino acid sequence determination and analysis, sequence comparisons
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