4.2.1.B8: etheroleic acid synthase

This is an abbreviated version!
For detailed information about etheroleic acid synthase, go to the full flat file.

Reaction

Synonyms

CYP74M3, CYP74Q1, DES, divinyl ether synthase, SmDES2

ECTree

     4 Lyases

         4.2 Carbon-oxygen lyases

             4.2.1 Hydro-lyases

                4.2.1.B8 etheroleic acid synthase

Advanced search results

Do not include text mining results

Include results (more...)

Include results (more...)

Results	in table
1	AA Sequence
2	Cloned(Commentary)
2	General Information
4	kcat/KM [mM/s]
4	KM Value [mM]
2	Localization
6	Natural Substrates/ Products (Substrates)
7	Organism
2	pH Optimum
1	Reaction
7	Reference
6	Source Tissue
19	Substrates and Products (Substrate)
5	Synonyms
1	Systematic Name
2	Temperature Optimum [°C]
4	Turnover Number [1/s]

Substrates Products

print visible entries

print all entries

Go back to the abbreviated version
of the Enzyme Summary Page.

Substrates Products on EC 4.2.1.B8 - etheroleic acid synthase

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.

top print hide show all columns Go to Substrate/Product Search

Please wait a moment until the data is sorted. This message will disappear when the data is sorted.

SUBSTRATE

PRODUCT                       

REACTION DIAGRAM

ORGANISM

UNIPROT

COMMENTARY
(Substrate)

LITERATURE
(Substrate)

COMMENTARY
(Product)

LITERATURE
(Product)

Reversibility
r=reversible
ir=irreversible
?=not specified

(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid

?

Convallaria majalis

-

poor substrate

706123

-

-

?

(9Z,11E,13R)-13-hydroperoxy-9,11-octadecadienoate

(9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O

Allium sativum

-

is utilized more slowly than (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate

703689

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

Allium sativum

-

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

703529

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

6 entries

(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid

(9Z,11E)-12-[(1'Z)-hexenyloxy]-9,11-dodecadienoic acid

Ranunculus acris

-

-

729304

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

Selaginella moellendorffii

D8QZ31

i.e. 13-HPOD

747182

-

-

?

(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoate

(9Z,11E)-12-[(1'Z,3'Z)-hexadienyloxy]-9,11-dodecadienoate + H2O

Ranunculus acris

-

highly preferred substrate

729304

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

Allium sativum

-

-

703529

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

Selaginella moellendorffii

D8QZ31

i.e. 13-HPOT

747182

-

-

?

additional information

?

-

6 entries

(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate

(9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O

Allium sativum

-

-

703689

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

Allium sativum

-

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

703621

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

Allium sativum

-

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

703621

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

Allium sativum

-

no activity with (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate

703689

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

Allium sativum

-

the enzyme uses preferentially 13-hydroperoxides as substrates and efficiently converts them into divinyl ether fatty acids

703688

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

Convallaria majalis

-

(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate is the preferred substrate

706123

i.e. etheroleic acid

-

?

additional information

?

-

Allium sativum

-

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

703621

-

-

?

additional information

?

-

Allium sativum

-

low activity with 13-hydroperoxy-octadecatrienoate

703689

-

-

?

additional information

?

-

Ranunculus acris

-

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

729304

-

-

?

additional information

?

-

Ranunculus acris

-

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

729304

-

-

?

additional information

?

-

Selaginella moellendorffii

D8QZ31

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)

747182

-

-

?

additional information

?

-

Selaginella moellendorffii

-

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)

747182

-

-

?