4.2.1.B8 (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid poor substrate Convallaria majalis ? - ? 407613 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 ? 407617 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 ? 406971 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 ? 406971 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 ? 406971 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 ? 406971 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 ? 406971 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 ? 406971 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 ? 407619 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 ? 429105