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Information on EC 4.2.1.B8 - etheroleic acid synthase
for references in articles please use BRENDA:EC4.2.1.B8preliminary BRENDA-supplied EC number
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EC Tree
4.2.1.B8 etheroleic acid synthaseSpecify your search results
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
cyp74m3, cyp74q1, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
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REACTION
REACTION DIAGRAM
COMMENTARY
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
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-
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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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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid
?
-
poor substrate
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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
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is utilized more slowly than (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
i.e. etheroleic acid
-
?
(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
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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
-
?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
(9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
(9Z,11E)-12-[(1'Z)-hexenyloxy]-9,11-dodecadienoic acid
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-
i.e. (omega5Z)-etherolenic acid
-
?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
(9Z,11E)-12[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
i.e. 13-HPOD
-
-
?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoate
(9Z,11E)-12-[(1'Z,3'Z)-hexadienyloxy]-9,11-dodecadienoate + H2O
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highly preferred substrate
i.e. etherolenic acid
-
?
(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
-
-
i.e. etherolenic acid
-
?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
(9Z,11E)-12[(1Z,3Z)-hexa-1,3-dien-1-yloxy]dodeca-9,11-dienoic acid + H2O
i.e. 13-HPOT
-
-
?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
(9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
-
-
i.e. etheroleic acid
-
?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
(9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
-
an essentially complete loss of isotope is noted with the (14R)-deuterated precursor, whereas incubation of the (14S)-deuterated precursor affords products that retain most of the deuterium label
i.e. etheroleic acid
-
?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
(9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
-
an essentially complete loss of isotope is noted with the (14R)-deuterated precursor, whereas incubation of the (14S)-deuterated precursor affords products that retained most of the deuterium label
i.e. etheroleic acid
-
?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
(9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
-
no activity with (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
i.e. etheroleic acid
-
?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
(9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
-
the enzyme uses preferentially 13-hydroperoxides as substrates and efficiently converts them into divinyl ether fatty acids
i.e. etheroleic acid
-
?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
(9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
-
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate is the preferred substrate
i.e. etheroleic acid
-
?
additional information
?
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irrespective of which hydroperoxide regioisomer serves as the substrate, divinyl ether synthases abstracting the pro-R hydrogen generate divinyl ethers having an E vinyl ether double bond, whereas enzymes abstracting the pro-S hydrogen produce divinyl ethers having a Z vinyl ether double bond
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-
?
additional information
?
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low activity with 13-hydroperoxy-octadecatrienoate
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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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-
?
additional information
?
-
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no activity with (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid and (9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid, high substrate specificity, overview. Product identification by GC-MS analyses
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-
?
additional information
?
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products are analyzed by gas chromatography-mass spectrometry, individual oxylipins are purified by HPLC and finally identified by their NMR data, including the 1H NMR, 2D-COSY, HSQC and HMBC, overview. Enzyme CYP74M3 (SmDES2) converts 13-HPOT and 13-HPOD mainly to etherolenic and etheroleic acids, respectively, via an (E)-vinyl ether radial intermediate. The enzyme is inactive towards (9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid (9-HPOT) and (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid (9-HPOD)
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?
additional information
?
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products are analyzed by gas chromatography-mass spectrometry, individual oxylipins are purified by HPLC and finally identified by their NMR data, including the 1H NMR, 2D-COSY, HSQC and HMBC, overview. Enzyme CYP74M3 (SmDES2) converts 13-HPOT and 13-HPOD mainly to etherolenic and etheroleic acids, respectively, via an (E)-vinyl ether radial intermediate. The enzyme is inactive towards (9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid (9-HPOT) and (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid (9-HPOD)
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?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate
(9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
-
-
i.e. etheroleic acid
-
?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
(9Z,11E)-12-[(1'Z)-hexenyloxy]-9,11-dodecadienoic acid
-
-
i.e. (omega5Z)-etherolenic acid
-
?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
(9Z,11E)-12[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O
i.e. 13-HPOD
-
-
?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoate
(9Z,11E)-12-[(1'Z,3'Z)-hexadienyloxy]-9,11-dodecadienoate + H2O
-
highly preferred substrate
i.e. etherolenic acid
-
?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
(9Z,11E)-12[(1Z,3Z)-hexa-1,3-dien-1-yloxy]dodeca-9,11-dienoic acid + H2O
i.e. 13-HPOT
-
-
?
additional information
?
-
-
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
LITERATURE
IMAGE
0.0431
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienate
-
pH 7.5, 25°C
0.0893
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
pH 7.5, 25°C, recombinant enzyme
0.0723
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
pH 7.5, 25°C, recombinant enzyme
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
266.7
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
pH 7.5, 25°C, recombinant enzyme
193.5
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
pH 7.5, 25°C, recombinant enzyme
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0031
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienate
-
pH 7.5, 25°C
2986.6
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
pH 7.5, 25°C, recombinant enzyme
2676.3
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
pH 7.5, 25°C, recombinant enzyme
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.5
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
25
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene CYP74M1 , DNA and amino acid sequence determination and analysis, sequence comparisons and unrooted phylogenetic tree, recombinant expression in Escherichia coli strain Rosetta-gami(DE3)pLysS B
gene CYP74Q1, DNA and amino acid sequence determination and analysis, sequence comparisons
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Grechkin, A.N.; Ilyasov, A.V.; Hamberg, M.
On the mechanism of biosynthesis of divinyl ether oxylipins by enzyme from garlic bulbs
Eur. J. Biochem.
245
137-142
1997
Allium sativum
brenda
Hamberg, M.
Hidden stereospecificity in the biosynthesis of divinyl ether fatty acids
FEBS J.
272
736-743
2005
Allium sativum
brenda
Grechkin, A.N.; Fazliev, F.N.; Mukhtarova, L.S.
The lipoxygenase pathway in garlic (Allium sativum L.) bulbs: detection of the novel divinyl ether oxylipins
FEBS Lett.
371
159-162
1995
Allium sativum
brenda
Grechkin, A.N.; Hamberg, M.
Divinyl ether synthase from garlic (Allium sativum L.) bulbs: sub-cellular localization and substrate regio-and stereospecificity
FEBS Lett.
388
112-114
1996
Allium sativum
brenda
Ogorodnikova, A.V.; Latypova, L.R.; Mukhitova, F.K.; Mukhtarova, L.S.; Grechkin, A.N.
Detection of divinyl ether synthase in Lily-of-the-Valley (Convallaria majalis) roots
Phytochemistry
69
2793-2798
2008
Convallaria majalis
brenda
Gorina, S.S.; Toporkova, Y.Y.; Mukhtarova, L.S.; Chechetkin, I.R.; Khairutdinov, B.I.; Gogolev, Y.V.; Grechkin, A.N.
Detection and molecular cloning of CYP74Q1 gene: identification of Ranunculus acris leaf divinyl ether synthase
Biochim. Biophys. Acta
1841
1227-1233
2014
Ranunculus acris
brenda
Gorina, S.S.; Toporkova, Y.Y.; Mukhtarova, L.S.; Smirnova, E.O.; Chechetkin, I.R.; Khairutdinov, B.I.; Gogolev, Y.V.; Grechkin, A.N.
Oxylipin biosynthesis in spikemoss Selaginella moellendorffii molecular cloning and identification of divinyl ether synthases CYP74M1and CYP74M3
Biochim. Biophys. Acta
1861
301-309
2016
Selaginella moellendorffii (D8QZ31), Selaginella moellendorffii
brenda
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