EC Number |
Substrates |
Organism |
Products |
Reversibility |
---|
4.2.1.B8 | (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid |
poor substrate |
Convallaria majalis |
? |
- |
? |
4.2.1.B8 | (9Z,11E,13R)-13-hydroperoxy-9,11-octadecadienoate |
is utilized more slowly than (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate |
Allium sativum |
(9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O |
i.e. etheroleic acid |
? |
4.2.1.B8 | (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate |
- |
Allium sativum |
(9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O |
i.e. etheroleic acid |
? |
4.2.1.B8 | (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate |
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate is the preferred substrate |
Convallaria majalis |
(9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O |
i.e. etheroleic acid |
? |
4.2.1.B8 | (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate |
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 |
Allium sativum |
(9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O |
i.e. etheroleic acid |
? |
4.2.1.B8 | (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate |
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 |
Allium sativum |
(9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O |
i.e. etheroleic acid |
? |
4.2.1.B8 | (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate |
no activity with (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate |
Allium sativum |
(9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O |
i.e. etheroleic acid |
? |
4.2.1.B8 | (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate |
the enzyme uses preferentially 13-hydroperoxides as substrates and efficiently converts them into divinyl ether fatty acids |
Allium sativum |
(9Z,11E)-12-[(1E)-hex-1-en-1-yloxy]dodeca-9,11-dienoic acid + H2O |
i.e. etheroleic acid |
? |
4.2.1.B8 | (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoate |
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 |
Allium sativum |
(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 |
two isomers of etheroleic acid are isolated |
? |
4.2.1.B8 | (9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid |
- |
Ranunculus acris |
(9Z,11E)-12-[(1'Z)-hexenyloxy]-9,11-dodecadienoic acid |
i.e. (omega5Z)-etherolenic acid |
? |