4.2.1.92: hydroperoxide dehydratase
This is an abbreviated version!
For detailed information about hydroperoxide dehydratase, go to the full flat file.
Word Map on EC 4.2.1.92
-
4.2.1.92
-
lipoxygenase
-
jasmonic
-
oxylipins
-
linolenic
-
12-oxo-phytodienoic
-
aroma
-
hevea
-
divinyl
-
epoxyalcohols
-
9-hydroperoxides
-
lyases
-
cyclopentenone
-
alpha-linolenic
-
13-hpot
-
13-lipoxygenase
-
wound-induced
-
octadecanoids
-
laticifer
-
alpha-ketols
-
aloxe3
-
12r-lox
-
13-hydroperoxy
-
e-2-hexenal
-
hepoxilins
-
homomalla
-
coronatine
-
homolytic
-
hexenal
-
heterolytic
-
gaeumannomyces
-
antarafacial
-
attenuata
-
plexaura
-
food industry
-
medicine
-
synthesis
- 4.2.1.92
- lipoxygenase
-
jasmonic
- oxylipins
-
linolenic
-
12-oxo-phytodienoic
- aroma
- hevea
-
divinyl
- epoxyalcohols
-
9-hydroperoxides
- lyases
-
cyclopentenone
-
alpha-linolenic
-
13-hpot
-
13-lipoxygenase
-
wound-induced
-
octadecanoids
-
laticifer
-
alpha-ketols
- aloxe3
- 12r-lox
-
13-hydroperoxy
- e-2-hexenal
-
hepoxilins
- homomalla
-
coronatine
-
homolytic
- hexenal
-
heterolytic
-
gaeumannomyces
-
antarafacial
- attenuata
-
plexaura
- food industry
- medicine
- synthesis
Reaction
Synonyms
10S-hydroperoxide lyase, 13-HPL, 13-hydroperoxide lyase, 13-hydroperoxide-lyase, 13HPL, 13S-hydroperoxide-dependent peroxidase, 5,8-hydroperoxide isomerase, 8,11-hydroperoxide isomerase, 9-HPL, 9/13 hydroperoxide lyase, 9R-DOX-AOS, 9S-DOX-AOS, allene oxide synthase, allene oxide synthase-1, AOS, AOS1, AOS2, cAOS, catalase-related allene oxide synthase, CmHPL, Csa_7G075590, CsHPL, CYP74, CYP741, CYP742, CYP74A, CYP74B, CYP74B24, CYP74c, CYP74C13_GM, CYP74C13_MT, CYP74C1_CS, CYP74C2, CYP74C31, CYP74C4_ST, cytochrome P450 74A, EC 5.3.99.1, eLOX3, fatty acid 9-hydroperoxide lyase, fatty acid hydroperoxide lyase, fatty acid hydroperoxide-metabolizing enzyme, Fg-cat, FG02216.1, FGSG_02217, FOXB_01332, HPI, HPL, HPL1, HPLS, HPO lyase, HPO-lyase, hydroperoxide dehydrase, hydroperoxide isomerase, hydroperoxide lyase, hydroperoxide lyase 1, hydroperoxidehydrase, isomerase, hydroperoxide, KC525886, linoleate hydroperoxide isomerase, linoleic acid hydroperoxide isomerase, LOX, Mn-LO, More, MtrunA17_Chr4g0034141, Npun_R5469, OsAOS1, OsHPL3, OsHPL3/CYP74B2, RPP, rubber particle protein
ECTree
4.2.1.92 hydroperoxide dehydrataseAdvanced search results
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results (Substrates Products
Substrates Products on EC 4.2.1.92 - hydroperoxide dehydratase
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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
(12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoic acid
(8R)-hydroxy-(11R,12R)-epoxyeicosa-(5Z,9E,14Z)-trienoic acid + H2O
(12S)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoic acid
(10R)-hydroxy-(11S,12S)-epoxyeicosa-(5Z,8Z,14Z)-trienoic acid + (8R)-hydroxy-(11S,12S)-epoxyeicosa-(5Z,9E,14Z)-trienoic acid + H2O
-
-
the former being a isomer of hepoxilin A3, ration of products is 2:1
?
(13R)-hydroperoxylinolenic acid
13-ketolinolenic acid + threo-11-hydroxy-(12R,13R)-epoxy-(9Z,15Z)-octadecadienoic acid + erythro-11-hydroxy-(12R,13R)-epoxy-(9Z,15Z)-octadecadienoic acid
the G316A mutant converts (13R)-hydroperoxylinolenic acid to 13-ketolinolenic acid (with an apparent Km of 0.01 mM) and to epoxyalcohols viz. erythro- and threo-11-hydroxy-(12R,13R)-epoxy-(9Z,15Z)-octadecadienoic acids and one of the corresponding cis-epoxides as major products
-
-
?
(13S)-hydroperoxy-(9Z,11E)-octadecadienoic acid
(12,13S)-oxido-(9Z,11)-octadecadienoic acid + H2O
(13S)-hydroperoxy-(9Z,11E)-octadecadienoic acid
(12S,13S)-oxido-(9Z,11)-octadecadienoic acid + H2O
(13S)-hydroperoxy-(9Z,11E,15Z)-octadecatrienoic acid
(12,13S)-epoxy-(9Z,11,15Z)-octadecatrienoic acid + H2O
-
-
12-oxo-13-hydroxy-(9Z,15Z)-octadecadienoic acid + 12-oxo-(10,15Z)-phytodienoic acid, formed by spontaneous chemical or enzyme-catalyzed cyclization
?
(13S)-hydroperoxy-(9Z,11Z,15Z)-octadecatrienoic acid
(12,13S)-epoxy-(9Z,11Z,15Z)-octadecatrienoic acid + H2O
by AOS1
-
-
?
(13S)-hydroperoxyoctadecadienoic acid
13-hydroxy-12-oxo-9(Z)-octadecenoic acid + 12-oxo-10-phytoenoic acid
-
-
13-hydroxy-12-oxo-(9Z)-octadecenoic acid is the major product
-
?
(13S)-hydroperoxyoctadecatrienoic acid
13-hydroxy-12-oxo-(9Z,15Z)-octadecadienoic acid + 12-oxo-(10Z,15Z)-phytodienoic acid
-
-
OsAOS1 produces a 1:1 racemic mixture of cis-(+)/cis-(-)-12-oxo-(10Z,15Z)-phytodienoic acid via non-enzymatic cyclization of 12,13-epoxy-9,11,15-octadecatrienoic acid, an unstable allene oxide
-
?
(13S,9Z,11E,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
?
-
is converted to an allene oxide
-
-
?
(15S)-hydroperoxyeicosatetraenoic acid
(15S)-hydroxy-11,12-epoxyeicosatrienoic acid + H2O
-
-
-
-
?
(5Z,8Z,11E,13Z,15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoic acid
14,15-hepoxilin A3 + 14,15-hepoxilin B3 + H2O
(8E,10S,12Z)-10-hydroperoxyoctadeca-8,12-dienoic acid
(8E)-10-oxodecenoic acid + 1-octen-3-ol + (2Z)-octen-1-ol
the catalase-related hemoprotein reacts rapidly and specifically with linoleate 10S-hydroperoxide with a hydroperoxide lyase activity specific for the 10S-hydroperoxy enantiomer
in a 3:1 ratio, strict enzymatic control in formation of the 3R alcohol configuration with 99% enantiomeric excess
-
?
(8R)-hydroperoxy-(9Z,12Z)-octadecadienoic acid
(7S,8S)-dihydroxy-(9Z,12Z)-octadecadienoic acid + H2O
(8R)-hydroperoxylinoleic acid + H2O
(5S,8R)-dihydroxylinoleic acid
-
-
-
-
?
(8R)-hydroperoxylinoleic acid + H2O
(8R,11S)-dihydroxylinoleic acid
-
-
-
-
?
(8R)-hydroxyeicosatetraenoic acid
(8R)-hydroxy-(9R,10R)-trans-epoxy-eicosa-(5Z,11Z,14Z)-trienoic acid
-
the native, unmodified enzyme shows no activity with (8R)-hydroxyeicosatetraenoic acid, but the oxidized enzyme epoxidizes the substrate analogue stereospecifically on the 9,10-double bond to form (8R)-hydroxy-(9R,10R)-trans-epoxy-eicosa-(5Z,11Z,14Z)-trienoic acid as the predominant product, via Compound I (FeV=O) intermediate
erythro and threo diastereomers of (8R)-hydroxy-9,10-trans-epoxy-eicosa-5Z,11Z,14Z-trienoate
-
?
(9R)-hydroperoxy-(10E,12Z,15Z)-octadecatrienoic acid
9-hydroxy-10-oxo-(12Z,15Z)-octadecadienoic acid
(9R,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid
(9R,10)-10-epoxy-(10Z,12Z)-octadecadienoic acid
(9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid
(9S,10)-10-epoxy-(10Z,12Z)-octadecadienoic acid + H2O
recombinant FOXB_01332 oxidizes 18:2n-6 to (9S)-hydroperoxy-10(E),12(Z)-octadecadienoic acid by hydrogen abstraction and antarafacial insertion of molecular oxygen and sequentially to an allene oxide, (90S)-(10)-epoxy-10,12(Z)-octadecadienoic acid, which gives nonenzymatic hydrolysis products alpha- and gamma-ketols
-
-
?
(9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid
(9S,10)-epoxy-(10Z,12Z)-octadecadienoic acid + H2O
(9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid
10-oxo-(9R)-hydroxy-cis-12-octadecadienoic acid + H2O
(9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid
9-oxononanoic acid + (3Z)-nonenal
-
-
-
-
?
(9S)-hydroperoxy-(10E,12Z,15Z)-octadecatrienoic acid
(9S,10)-epoxy-(10Z,12Z,15Z)-octadecatrienoic acid + H2O
-
-
-
?
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid
(9S,10S,11S,12Z)-9,10-epoxy-11-hydroxy-12-octadecenoic acid + (9Z)-12-hydroxy-9-dodecenoic acid + ?
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid
(9S,10S,11S,12Z)-9,10-epoxy-11-hydroxy-12-octadecenoic acid + 9-hydroxy-10-oxo-12-octadecenoic acid + (9Z)-12-hydroxy-9-dodecenoic acid + H2O + ?
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid
(9Z)-12-hydroxy-9-dodecenoic acid + ?
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid
9-hydroxynonanoic acid + (9Z)-12-hydroxy-9-dodecenoic acid + ?
(9Z,11E,13R)-13-hydroperoxyoctadeca-9,11-dienoic acid
11-hydroxy-12(13)-epoxy-octadecadienoic acid + 9-hydroxy-12(13)-epoxy-octadecadienoic acid + H2O
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
(9Z)-12-hydroxy-9-dodecenoic acid + (10E)-12-hydroxy-10-dodecenoic acid + ?
-
-
-
?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
11-hydroxy-12,13-epoxy-9-octadecenoic acid + 9-hydroxy-12,13-epoxy-10-octadecenoic acid + (9Z)-12-hydroxy-9-dodecenoic acid + (10E)-12-hydroxy-10-dodecenoic acid + ?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
(9Z)-12-hydroxy-9-dodecenoic acid + (10E)-12-hydroxy-10-dodecenoic acid + ?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
(Z)-3-hexenal + 12-oxo-9-dodecenoic acid
(9Z,11E,15Z)-(13S)-hydroperoxyoctadeca-9,11,15-trienoate
(9Z,15Z)-(13S)-12,13-epoxyoctadeca-9,11,15-trienoate + H2O
13-hydroperoxy-(10E,12Z)-octadecadienoic acid
11-hydroxy-12(13)-epoxy-octadecadienoic acid + 9-hydroxy-12(13)-epoxy-octadecadienoic acid + H2O
13-hydroperoxy-9,11-octadecadienoic acid
(10E,12Z)-12-[(3S)-3-methyl-3-propyloxiran-2-ylidene]dodec-10-enoic acid + H2O
-
wild-type AOS activity
-
-
?
13-hydroperoxy-9,11-octadecadienoic acid
(10E,12Z)-13-[(2-hydroxypentan-2-yl)oxy]trideca-10,12-dienoic acid + H2O
-
activity of AOS mutant F137L
-
-
?
13-hydroperoxylinoleic acid
(Z)-3-hexanal + 12-oxododecenoic acid
-
-
-
-
?
13-hydroperoxylinolenic acid
12-oxo-cis-10,15-phytodienoic acid + (12Z,15Z)-9-hydroxy-10-oxooctadeca-12,15-dienoic acid + H2O
-
-
the latter is a minor product of approximately 5%
?
9-hydroperoxylinolenic acid
13-hydroxy-10-oxo-cis-15-trans-11-octadecadienoic acid + H2O
-
-
-
?
alpha-linolenic acid
(E,Z)-3,6-nonadienal + 9-oxononanoic acid
-
cleavage of 9-hydroperoxy fatty acid
-
-
?
heptadecatrienoic acid
12-hydroperoxyheptadecatrienoic acid + (8Z,10S,11Z,14Z)-10-hydroperoxyheptadeca-8,11,14-trienoic acid
the G316A mutant transforms 17:3n-3 to both 12-hydroperoxyheptadecatrienoic acid (about 93%) and 10-hydroperoxyheptadecatrienoic acid (7%)
-
-
?
linoleate hydroperoxide + H2O
9,12,13-trihydroxy-trans-10-octadecenoic acid + 9,10,13-trihydroxy-trans-11-octadecenoic acid
-
-
-
-
?
linoleic acid
(Z)-3-nonenal + 9-oxononanoic acid
-
cleavage of 9-hydroperoxy fatty acid
-
-
?
linoleic acid
?
Mn-LO G316A metabolizeS 18:2n-6 to (11S)-hydroperoxyoctadecadienoic acid and (13R)-hydroperoxyoctadecadienoic acid in approximately the same relative amounts as the native enzyme, and (13R)-hydroperoxyoctadecadienoic acid accumulates as the end product
-
-
?
linolenic acid
(13R)-hydroperoxyoctadecatrienoic acid + (11S)-hydroperoxyoctadecatrienoic acid
Mn-LO G316A metabolizes 18:3n-3 to (13R)-hydroperoxyoctadecatrienoic acid and (11S)-hydroperoxyoctadecatrienoic acid
-
-
?
linolic acid hydroperoxide + H2O
9,12,13-trihydroxy-trans-10-octadecenoic acid + 9,10,13-trihydroxy-trans-11-octadecenoic acid
-
-
-
?
(12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoic acid
(8R)-hydroxy-(11R,12R)-epoxyeicosa-(5Z,9E,14Z)-trienoic acid + H2O
-
intramolecular oxygenation with retention of the configuration of the carbon atom hydroxylated
-
?
(12R)-hydroperoxy-(5Z,8Z,10E,14Z)-eicosatetraenoic acid
(8R)-hydroxy-(11R,12R)-epoxyeicosa-(5Z,9E,14Z)-trienoic acid + H2O
-
poor substrate
-
-
?
(13S)-hydroperoxy-(9Z,11E)-octadecadienoic acid
(12,13S)-oxido-(9Z,11)-octadecadienoic acid + H2O
-
-
-
?
(13S)-hydroperoxy-(9Z,11E)-octadecadienoic acid
(12,13S)-oxido-(9Z,11)-octadecadienoic acid + H2O
-
-
-
?
(13S)-hydroperoxy-(9Z,11E)-octadecadienoic acid
(12,13S)-oxido-(9Z,11)-octadecadienoic acid + H2O
-
-
-
?
(13S)-hydroperoxy-(9Z,11E)-octadecadienoic acid
(12,13S)-oxido-(9Z,11)-octadecadienoic acid + H2O
-
-
-
?
(13S)-hydroperoxy-(9Z,11E)-octadecadienoic acid
(12,13S)-oxido-(9Z,11)-octadecadienoic acid + H2O
-
-
-
?
(13S)-hydroperoxy-(9Z,11E)-octadecadienoic acid
(12,13S)-oxido-(9Z,11)-octadecadienoic acid + H2O
-
-
-
?
(13S)-hydroperoxy-(9Z,11E)-octadecadienoic acid
(12S,13S)-oxido-(9Z,11)-octadecadienoic acid + H2O
-
-
-
?
(13S)-hydroperoxy-(9Z,11E)-octadecadienoic acid
(12S,13S)-oxido-(9Z,11)-octadecadienoic acid + H2O
-
-
-
?
(13S)-hydroperoxy-(9Z,11E)-octadecadienoic acid
(12S,13S)-oxido-(9Z,11)-octadecadienoic acid + H2O
-
substrate listed without specification of steroisomer used
products are 10,13-dihydroxyoctadec-11-enoic acid + 12,13-dihydroxyoctadec-9-enoic acid + trace amounts of 9,12-dihydroxyoctadec-10-enoic acid
?
(13S)-hydroperoxy-(9Z,11E)-octadecadienoic acid
(12S,13S)-oxido-(9Z,11)-octadecadienoic acid + H2O
-
-
-
-
?
(13S)-hydroperoxy-(9Z,11E)-octadecadienoic acid
(12S,13S)-oxido-(9Z,11)-octadecadienoic acid + H2O
-
(S)-hydroperoxy-(9Z,11E)-octadecadienoic acid is a poor substrate
products are: (11R,12R)-epoxy-(13S)-hydroxy-(9Z)-octadecenoic acid + (9S,10R)-epoxy-(13S)-hydroxy-(11E)-octadecenoic acid
?
(13S)-hydroperoxy-(9Z,11E)-octadecadienoic acid
(12S,13S)-oxido-(9Z,11)-octadecadienoic acid + H2O
-
-
products are: 13-hydroxy-12-oxo-cis-9-octadecenoic acid + small amounts of the gamma ketol
?
(13S)-hydroperoxy-(9Z,11E)-octadecadienoic acid
(12S,13S)-oxido-(9Z,11)-octadecadienoic acid + H2O
-
-
-
?
(13S)-hydroperoxy-(9Z,11E)-octadecadienoic acid
(12S,13S)-oxido-(9Z,11)-octadecadienoic acid + H2O
-
-
spontaneous hydrolysis to 12-keto-13-hydroxy-(9Z)-octadecenoic acid (72% 13(R) and 28% 13(S))
?
(5Z,8Z,11E,13Z,15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoic acid
14,15-hepoxilin A3 + 14,15-hepoxilin B3 + H2O
-
high stereoselectivity, not with 15(R)-substrate
mixture of both products
?
(5Z,8Z,11E,13Z,15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoic acid
14,15-hepoxilin A3 + 14,15-hepoxilin B3 + H2O
-
poor substrate
-
-
?
(8R)-hydroperoxy-(9Z,12Z)-octadecadienoic acid
(7S,8S)-dihydroxy-(9Z,12Z)-octadecadienoic acid + H2O
-
-
-
-
?
(8R)-hydroperoxy-(9Z,12Z)-octadecadienoic acid
(7S,8S)-dihydroxy-(9Z,12Z)-octadecadienoic acid + H2O
-
-
-
?
(8R)-hydroperoxy-(9Z,12Z)-octadecadienoic acid
(7S,8S)-dihydroxy-(9Z,12Z)-octadecadienoic acid + H2O
-
-
-
?
(8R)-hydroperoxy-(9Z,12Z)-octadecadienoic acid
(7S,8S)-dihydroxy-(9Z,12Z)-octadecadienoic acid + H2O
-
stereospecific elimination of the pro-S hydrogen from C-7 and intramolecular suprafacial insertion of oxygen at C-7 with retention of the absolute configuration at C-7
-
?
(8R)-hydroperoxy-(9Z,12Z)-octadecadienoic acid
(7S,8S)-dihydroxy-(9Z,12Z)-octadecadienoic acid + H2O
-
-
-
-
?
(8R)-hydroperoxy-(9Z,12Z)-octadecadienoic acid
(7S,8S)-dihydroxy-(9Z,12Z)-octadecadienoic acid + H2O
-
stereospecific elimination of the pro-S hydrogen from C-7 and intramolecular suprafacial insertion of oxygen at C-7 with retention of the absolute configuration at C-7
-
?
(8R)-hydroperoxy-(9Z,12Z)-octadecadienoic acid
(7S,8S)-dihydroxy-(9Z,12Z)-octadecadienoic acid + H2O
-
poor substrate
-
-
?
(8R)-hydroperoxyeicosatetraenoic acid
?
-
the substrate is converted to an unstable allene oxide product via the FeIV-OH intermediate, Compound II, the native enzyme shows a strong preference for its natural substrate
-
-
?
(8R)-hydroperoxyeicosatetraenoic acid
?
-
the substrate is converted to an unstable allene oxide product via the FeIV-OH intermediate, Compound II
-
-
?
(9R)-hydroperoxy-(10E,12Z,15Z)-octadecatrienoic acid
9-hydroxy-10-oxo-(12Z,15Z)-octadecadienoic acid
-
-
-
-
?
(9R)-hydroperoxy-(10E,12Z,15Z)-octadecatrienoic acid
9-hydroxy-10-oxo-(12Z,15Z)-octadecadienoic acid
-
-
-
-
?
(9R)-hydroperoxy-(10E,12Z,15Z)-octadecatrienoic acid
9-hydroxy-10-oxo-(12Z,15Z)-octadecadienoic acid
-
-
-
-
?
(9R)-hydroperoxy-(10E,12Z,15Z)-octadecatrienoic acid
9-hydroxy-10-oxo-(12Z,15Z)-octadecadienoic acid
-
-
-
-
?
(9R,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid
(9R,10)-10-epoxy-(10Z,12Z)-octadecadienoic acid
-
an unstable allene oxide
-
?
(9R,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid
(9R,10)-10-epoxy-(10Z,12Z)-octadecadienoic acid
-
an unstable allene oxide
-
?
(9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid
(9S,10)-epoxy-(10Z,12Z)-octadecadienoic acid + H2O
recombinant FOXB_01332 oxidizes 18:2n-6 to (9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid by hydrogen abstraction and antarafacial insertion of molecular oxygen and sequentially to an allene oxide, (9S,10)-epoxy-(10Z,12Z)-octadecadienoic acid, which gives nonenzymatic hydrolysis products alpha- and gamma-ketols
-
-
?
(9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid
(9S,10)-epoxy-(10Z,12Z)-octadecadienoic acid + H2O
recombinant FOXB_01332 oxidizes 18:2n-6 to (9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid by hydrogen abstraction and antarafacial insertion of molecular oxygen and sequentially to an allene oxide, (9S,10)-epoxy-(10Z,12Z)-octadecadienoic acid, which gives nonenzymatic hydrolysis products alpha- and gamma-ketols
-
-
?
(9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid
10-oxo-(9R)-hydroxy-cis-12-octadecadienoic acid + H2O
-
-
9-hydroxy-10-oxo,cis-12-octadecenoic acid and 13-hydroxy-10-oxo-trans-11-octadecenoic acid in the ratio 2:1
?
(9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid
10-oxo-(9R)-hydroxy-cis-12-octadecadienoic acid + H2O
-
(S)-hydroperoxy-(10E,12Z)-octadecadienoic acid is a poor substrate
products: (10R,11R)-epoxy-(9S)-hydroxy-(12Z)-octadecenoic acid + (12R,13S)-epoxy-(9S)-hydroxy-(10E)-octadecenoic acid
?
(9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid
10-oxo-(9R)-hydroxy-cis-12-octadecadienoic acid + H2O
-
-
-
-
?
(9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid
10-oxo-(9R)-hydroxy-cis-12-octadecadienoic acid + H2O
-
-
-
-
?
(9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid
10-oxo-(9R)-hydroxy-cis-12-octadecadienoic acid + H2O
-
-
in presence of linoleate the product is (9R)-linoleoyloxy-10-oxo-cis-12-octadecenoic acid
?
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid
(9S,10S,11S,12Z)-9,10-epoxy-11-hydroxy-12-octadecenoic acid + (9Z)-12-hydroxy-9-dodecenoic acid + ?
-
-
-
?
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid
(9S,10S,11S,12Z)-9,10-epoxy-11-hydroxy-12-octadecenoic acid + (9Z)-12-hydroxy-9-dodecenoic acid + ?
-
-
-
?
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid
(9S,10S,11S,12Z)-9,10-epoxy-11-hydroxy-12-octadecenoic acid + (9Z)-12-hydroxy-9-dodecenoic acid + ?
-
-
-
?
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid
(9S,10S,11S,12Z)-9,10-epoxy-11-hydroxy-12-octadecenoic acid + (9Z)-12-hydroxy-9-dodecenoic acid + ?
-
-
-
?
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid
(9S,10S,11S,12Z)-9,10-epoxy-11-hydroxy-12-octadecenoic acid + 9-hydroxy-10-oxo-12-octadecenoic acid + (9Z)-12-hydroxy-9-dodecenoic acid + H2O + ?
-
-
-
?
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid
(9S,10S,11S,12Z)-9,10-epoxy-11-hydroxy-12-octadecenoic acid + 9-hydroxy-10-oxo-12-octadecenoic acid + (9Z)-12-hydroxy-9-dodecenoic acid + H2O + ?
-
-
-
?
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid
?
-
the divinyl ether synthase enzyme mutant E292G shows allene oxide synthase activity, producing the typical allene oxide synthase product alpha-ketol and 12-oxo-10,15-phytodienoic acid, and lacks divinyl ether synthase activity in contrast to the wild-type divinyl ether synthase CYP74B16
-
-
?
(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid
?
-
the divinyl ether synthase enzyme mutant V379F shows allene oxide synthase activity, producing the typical allene oxide synthase product alpha-ketol, and lacks divinyl ether synthase activity in contrast to the wild-type divinyl ether synthase CYP74D3
-
-
?
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid
(9Z)-12-hydroxy-9-dodecenoic acid + ?
-
-
-
?
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid
(9Z)-12-hydroxy-9-dodecenoic acid + ?
-
-
-
?
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid
(9Z)-12-hydroxy-9-dodecenoic acid + ?
-
-
-
?
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid
9-hydroxynonanoic acid + (9Z)-12-hydroxy-9-dodecenoic acid + ?
-
-
-
?
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid
9-hydroxynonanoic acid + (9Z)-12-hydroxy-9-dodecenoic acid + ?
-
-
-
?
(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid
9-hydroxynonanoic acid + (9Z)-12-hydroxy-9-dodecenoic acid + ?
-
-
-
?
(9Z,11E,13R)-13-hydroperoxyoctadeca-9,11-dienoic acid
11-hydroxy-12(13)-epoxy-octadecadienoic acid + 9-hydroxy-12(13)-epoxy-octadecadienoic acid + H2O
-
-
-
?
(9Z,11E,13R)-13-hydroperoxyoctadeca-9,11-dienoic acid
11-hydroxy-12(13)-epoxy-octadecadienoic acid + 9-hydroxy-12(13)-epoxy-octadecadienoic acid + H2O
-
-
-
?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
11-hydroxy-12,13-epoxy-9-octadecenoic acid + 9-hydroxy-12,13-epoxy-10-octadecenoic acid + (9Z)-12-hydroxy-9-dodecenoic acid + (10E)-12-hydroxy-10-dodecenoic acid + ?
-
-
-
?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
11-hydroxy-12,13-epoxy-9-octadecenoic acid + 9-hydroxy-12,13-epoxy-10-octadecenoic acid + (9Z)-12-hydroxy-9-dodecenoic acid + (10E)-12-hydroxy-10-dodecenoic acid + ?
-
-
-
?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
11-hydroxy-12,13-epoxy-9-octadecenoic acid + 9-hydroxy-12,13-epoxy-10-octadecenoic acid + (9Z)-12-hydroxy-9-dodecenoic acid + (10E)-12-hydroxy-10-dodecenoic acid + ?
-
-
-
?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
11-hydroxy-12,13-epoxy-9-octadecenoic acid + 9-hydroxy-12,13-epoxy-10-octadecenoic acid + (9Z)-12-hydroxy-9-dodecenoic acid + (10E)-12-hydroxy-10-dodecenoic acid + ?
-
-
-
?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
hexanal + 12-oxo-9-dodecenoic acid
-
-
-
-
?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
hexanal + 12-oxo-9-dodecenoic acid
-
-
-
?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
hexanal + 12-oxo-9-dodecenoic acid
-
-
-
?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
hexanal + 12-oxo-9-dodecenoic acid
13-HPOD
-
-
?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
hexanal + 12-oxo-9-dodecenoic acid
-
-
-
-
?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
hexanal + 12-oxo-9-dodecenoic acid
-
-
-
-
?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
hexanal + 12-oxo-9-dodecenoic acid
-
-
-
?
(9Z,11E,13S)-13-hydroperoxy-9,11-octadecadienoic acid
hexanal + 12-oxo-9-dodecenoic acid
-
-
-
?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
(9Z)-12-hydroxy-9-dodecenoic acid + (10E)-12-hydroxy-10-dodecenoic acid + ?
-
-
-
?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
(9Z)-12-hydroxy-9-dodecenoic acid + (10E)-12-hydroxy-10-dodecenoic acid + ?
-
-
-
?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
(9Z)-12-hydroxy-9-dodecenoic acid + (10E)-12-hydroxy-10-dodecenoic acid + ?
-
-
-
?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
(9Z)-12-hydroxy-9-dodecenoic acid + (10E)-12-hydroxy-10-dodecenoic acid + ?
-
-
-
?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
(Z)-3-hexenal + 12-oxo-9-dodecenoic acid
-
-
-
-
?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
(Z)-3-hexenal + 12-oxo-9-dodecenoic acid
-
-
-
?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
(Z)-3-hexenal + 12-oxo-9-dodecenoic acid
-
-
-
?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
(Z)-3-hexenal + 12-oxo-9-dodecenoic acid
-
-
-
-
?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
(Z)-3-hexenal + 12-oxo-9-dodecenoic acid
-
-
-
-
?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
(Z)-3-hexenal + 12-oxo-9-dodecenoic acid
-
-
-
?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
(Z)-3-hexenal + 12-oxo-9-dodecenoic acid
-
-
-
?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
(Z)-3-hexenal + 12-oxo-9-dodecenoic acid
-
-
-
-
?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
?
-
the divinyl ether synthase enzyme mutant E292G shows allene oxide synthase activity, producing the typical allene oxide synthase product alpha-ketol and 12-oxo-10,15-phytodienoic acid, and lacks divinyl ether synthase activity in contrast to the wild-type divinyl ether synthase CYP74B16
-
-
?
(9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
?
-
the divinyl ether synthase enzyme mutant V379F shows allene oxide synthase activity, producing the typical allene oxide synthase product alpha-ketol, and lacks divinyl ether synthase activity in contrast to the wild-type divinyl ether synthase CYP74D3
-
-
?
(9Z,11E,15Z)-(13S)-hydroperoxyoctadeca-9,11,15-trienoate
(9Z,15Z)-(13S)-12,13-epoxyoctadeca-9,11,15-trienoate + H2O
-
-
-
?
(9Z,11E,15Z)-(13S)-hydroperoxyoctadeca-9,11,15-trienoate
(9Z,15Z)-(13S)-12,13-epoxyoctadeca-9,11,15-trienoate + H2O
-
-
-
?
13-hydroperoxy-(10E,12Z)-octadecadienoic acid
11-hydroxy-12(13)-epoxy-octadecadienoic acid + 9-hydroxy-12(13)-epoxy-octadecadienoic acid + H2O
-
-
-
?
13-hydroperoxy-(10E,12Z)-octadecadienoic acid
11-hydroxy-12(13)-epoxy-octadecadienoic acid + 9-hydroxy-12(13)-epoxy-octadecadienoic acid + H2O
-
-
-
?
additional information
?
-
the enzyme catalyzes the first specific reaction in the formation of 12-oxophytodienoic acid, a signaling compound with multiple functions that is also the immediate precursor of jasmonic acid
-
-
?
additional information
?
-
-
the enzyme catalyzes the first specific reaction in the formation of 12-oxophytodienoic acid, a signaling compound with multiple functions that is also the immediate precursor of jasmonic acid
-
-
?
additional information
?
-
galactoplid bound hydroperoxides are substrates for CYP74 members
-
-
?
additional information
?
-
-
two hydroperoxide isomerases in Aspergillus clavatus acting on hydroperoxylinoleic acid: the 5,8-linoleate diol synthase exhibiting 5,8-hydroperoxide isomerase activity, and the 8, 11-linoleate diol synthase exhibiting 8,11-hydroperoxide isomerase activity, overview
-
-
?
additional information
?
-
Asn964 may facilitate homolytic cleavage of the dioxygen bond of (9R)-hydroperoxy-10(E),12(Z)-octadecadienoic acid with formation of compound II. No activity with 18:2n-6
-
-
?
additional information
?
-
-
Asn964 may facilitate homolytic cleavage of the dioxygen bond of (9R)-hydroperoxy-10(E),12(Z)-octadecadienoic acid with formation of compound II. No activity with 18:2n-6
-
-
?
additional information
?
-
Asn964 may facilitate homolytic cleavage of the dioxygen bond of (9R)-hydroperoxy-10(E),12(Z)-octadecadienoic acid with formation of compound II. No activity with 18:2n-6
-
-
?
additional information
?
-
the recombinant enzyme (encoded by gene CYP74B24) produces (Z)-3-hexenal from 13-HPOT with the optimal pH 6.0 in vitro
-
-
?
additional information
?
-
-
the recombinant enzyme (encoded by gene CYP74B24) produces (Z)-3-hexenal from 13-HPOT with the optimal pH 6.0 in vitro
-
-
?
additional information
?
-
-
cleavage of 9-hydroperoxy fatty acids or 13-hydroperoxy fatty acids by a hydroperoxide lyase results in formation of aldehydes (Z)-3-nonenal/(E,Z)-3,6-nonadienal or (Z)-3-hexanal, and omega-oxo fatty acid 9-oxo-nonanoic acid or 12-oxo-dodecenoic acid, respectively
-
-
?
additional information
?
-
reaction products are identified and quantified using HPLC chromatography and mass spectrometry, product specificities, overview
-
-
?
additional information
?
-
reaction products are identified and quantified using HPLC chromatography and mass spectrometry, product specifities, overview. No activity with (9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
-
-
?
additional information
?
-
reaction products are identified and quantified using HPLC chromatography and mass spectrometry, product specificities, overview
-
-
?
additional information
?
-
reaction products are identified and quantified using HPLC chromatography and mass spectrometry, product specificities, overview
-
-
?
additional information
?
-
reaction products are identified and quantified using HPLC chromatography and mass spectrometry, product specifities, overview
-
-
?
additional information
?
-
reaction products are identified and quantified using HPLC chromatography and mass spectrometry, product specifities, overview
-
-
?
additional information
?
-
mechanism of formation of fatty acid diepoxy ketone, overview. No reaction with 9R- and 9S-hydroperoxy-9,11-octadecadienoates. Peroxidase assay monitoring the oxidation of 2,2'-azino-bis(3-ethylbenzothiazoline)-6-sulphonic acid (ABTS), enzyme Fg-cat exhibits robust activity (kcat 550 s/1) using the 13S-hydroperoxy-C18 fatty acids as the oxidizing co-substrate
-
-
?
additional information
?
-
-
mechanism of formation of fatty acid diepoxy ketone, overview. No reaction with 9R- and 9S-hydroperoxy-9,11-octadecadienoates. Peroxidase assay monitoring the oxidation of 2,2'-azino-bis(3-ethylbenzothiazoline)-6-sulphonic acid (ABTS), enzyme Fg-cat exhibits robust activity (kcat 550 s/1) using the 13S-hydroperoxy-C18 fatty acids as the oxidizing co-substrate
-
-
?
additional information
?
-
mechanism of formation of fatty acid diepoxy ketone, overview. No reaction with 9R- and 9S-hydroperoxy-9,11-octadecadienoates. Peroxidase assay monitoring the oxidation of 2,2'-azino-bis(3-ethylbenzothiazoline)-6-sulphonic acid (ABTS), enzyme Fg-cat exhibits robust activity (kcat 550 s/1) using the 13S-hydroperoxy-C18 fatty acids as the oxidizing co-substrate
-
-
?
additional information
?
-
FOXB_01332 is a linoleate 9-dioxygenase with homology to animal heme peroxidases and a 9-dioxygenase-allene oxide synthase fusion protein
-
-
?
additional information
?
-
-
FOXB_01332 is a linoleate 9-dioxygenase with homology to animal heme peroxidases and a 9-dioxygenase-allene oxide synthase fusion protein
-
-
?
additional information
?
-
(9S)-dioxygenase-allene oxide synthase converts 9S-hydroperoxyoctadecadienoic acid to alpha- and gamma-ketols, likely formed by hydrolysis of (9S,10)-(10)-epoxy-(10Z,12Z)-octadecadienoic acid, along with small amounts of epoxy alcohols. The (9R)-hydroperoxyoctadecadienoic acid preparation contains a few percent (9S)-hydroperoxyoctadecadienoic acid, and only the latter is apparently transformed to an alpha-ketol by (9S)-dioxygenase-allene oxide synthase. (13S)-hydroperoxyoctadecadienoic acid, (13S)-hydroxy-(10E,12Z,15Z)-octadecatrienoicacid, (13R)-hydroperoxyoctadecadienoic acid, and (13R)-hydroxy-(10E,12Z,15Z)-octadecatrienoicacid are not transformed to detectable amounts of allene oxides/alpha-ketols, but variable amounts of epoxy alcohols accumulate, mass spectrometric analysis of products, substrate specificity, overview
-
-
?
additional information
?
-
-
(9S)-dioxygenase-allene oxide synthase converts 9S-hydroperoxyoctadecadienoic acid to alpha- and gamma-ketols, likely formed by hydrolysis of (9S,10)-(10)-epoxy-(10Z,12Z)-octadecadienoic acid, along with small amounts of epoxy alcohols. The (9R)-hydroperoxyoctadecadienoic acid preparation contains a few percent (9S)-hydroperoxyoctadecadienoic acid, and only the latter is apparently transformed to an alpha-ketol by (9S)-dioxygenase-allene oxide synthase. (13S)-hydroperoxyoctadecadienoic acid, (13S)-hydroxy-(10E,12Z,15Z)-octadecatrienoicacid, (13R)-hydroperoxyoctadecadienoic acid, and (13R)-hydroxy-(10E,12Z,15Z)-octadecatrienoicacid are not transformed to detectable amounts of allene oxides/alpha-ketols, but variable amounts of epoxy alcohols accumulate, mass spectrometric analysis of products, substrate specificity, overview
-
-
?
additional information
?
-
FOXB_01332 is a linoleate 9-dioxygenase with homology to animal heme peroxidases and a 9-dioxygenase-allene oxide synthase fusion protein
-
-
?
additional information
?
-
(9S)-dioxygenase-allene oxide synthase converts 9S-hydroperoxyoctadecadienoic acid to alpha- and gamma-ketols, likely formed by hydrolysis of (9S,10)-(10)-epoxy-(10Z,12Z)-octadecadienoic acid, along with small amounts of epoxy alcohols. The (9R)-hydroperoxyoctadecadienoic acid preparation contains a few percent (9S)-hydroperoxyoctadecadienoic acid, and only the latter is apparently transformed to an alpha-ketol by (9S)-dioxygenase-allene oxide synthase. (13S)-hydroperoxyoctadecadienoic acid, (13S)-hydroxy-(10E,12Z,15Z)-octadecatrienoicacid, (13R)-hydroperoxyoctadecadienoic acid, and (13R)-hydroxy-(10E,12Z,15Z)-octadecatrienoicacid are not transformed to detectable amounts of allene oxides/alpha-ketols, but variable amounts of epoxy alcohols accumulate, mass spectrometric analysis of products, substrate specificity, overview
-
-
?
additional information
?
-
-
overview on substrates, configurations and mechanism
-
-
?
additional information
?
-
catalytic properties of Mn-LO and the G316A mutant with heptadecatrienic acid, 18:2n-6, octadecatrienoic acid, and nonadecatrienoic acid as substrates: increasing the fatty acid chain length from C17 to C19 shifts the oxygenation by Mn-LO from the n-6 toward the n-8 carbon. The G316A mutant increases the oxygenation at the n-8 carbon of 17:3n-3 and at the n-10 carbon of the C17 and C18 fatty acids (from 12% to 711%). The most striking effect of the G316A mutant is a 2fold, 7fold, and 15fold increase in transformation of the n-6 hydroperoxides of 19:3n-3, 18:3n-3, and 17:3n-3, respectively, to keto fatty acids and epoxyalcohols. The n-3 double bond is essential. Both oxygen atoms are retained in the epoxyalcohols. (R)-Hydroperoxides at n-6 of C17:3, 18:3, and 19:3 are transformed 5times faster than (S)-stereoisomers
-
-
?
additional information
?
-
reaction products are identified and quantified using HPLC chromatography and mass spectrometry, product specifities, overview
-
-
?
additional information
?
-
-
overview on substrates, configurations and mechanism
-
-
?
additional information
?
-
-
CYP74 enzymes use their fatty acid hydroperoxide substrate to activate the enzyme and substrate in one and the same step
-
-
?
additional information
?
-
reaction products are identified and quantified using HPLC chromatography and mass spectrometry, product specifities, overview
-
-
?
additional information
?
-
-
the enzyme cleaves 13(S)-hydroperoxy-C18 fatty acids into C6-aldehyde and C12-oxo-acid
-
-
?
additional information
?
-
-
the enzyme cleaves 13(S)-hydroperoxy-C18 fatty acids into C6-aldehyde and C12-oxo-acid. GC-MS product analysis
-
-
?
additional information
?
-
-
the enzyme cleaves 13(S)-hydroperoxy-C18 fatty acids into C6-aldehyde and C12-oxo-acid
-
-
?
additional information
?
-
-
the enzyme cleaves 13(S)-hydroperoxy-C18 fatty acids into C6-aldehyde and C12-oxo-acid. GC-MS product analysis
-
-
?
additional information
?
-
the enzyme mainly acts as an oleate or linoleate dioxygenase, albeit with alpha-linolenic acid very competitive at low substrate concentrations, substrate specificity and kinetics, overview
-
-
?
additional information
?
-
according to their specificity, HPLs can act on the 9- or 13-hydroperoxides of linoleic and linolenic acids (hydroperoxyoctadecadienoic acid (HPOD) and hydroperoxyoctadecatrienoic acid (HPOT)) and catalyze the cleavage of these hydroperoxides into C6- or C9-aldehydes and the C12- or C9-oxo-acids, respectively
-
-
?
additional information
?
-
the recombinant 13-HPL enzyme is assayed as biocatalyst to produce C6-aldehydes. Bioconversion of 13-hydroperoxides of linoleic and linolenic acids by recombinant enzyme with or without chloroplast targeting signal sequence, reaction products are identified and quantified using gas chromatography and mass spectrometry. Recombinant HPL enzyme with targeting sequence allows production of 5.61 mM hexanal and 4.39 mM (Z)-3-hexenal, corresponding to high conversion yields of 93.5% and 73%, respectively. The HPL enzyme without targeting sequence fails to obtain greater quantities of hexanal or (Z)-3-hexenal. No undesirable products are formed, and no isomerization of (Z)-3-hexenal in (E)-2-hexenal occurs
-
-
?
additional information
?
-
-
cleavage of 9-hydroperoxy fatty acids in vivo, AOS enzymes also convert hydroperoxy fatty acids to aldehydes via an HPL-like activity
-
-
?
additional information
?
-
-
OsHPL3 possesses intrinsic hydroperoxide lyase activity hydrolyzing hydroperoxylinolenic acid to produce green leaf volatiles, it catabolizes 9/13-hydroperoxylinoleic acid to form (Z)-3-hexenal
-
-
?
additional information
?
-
-
allene oxide synthase converts fatty acid hydroperoxides into unstable fatty acid epoxides (allene oxides). OsAOS1 exhibits dual positional substrate specificity and prefers 13-positional isomeric to 9-positional isomeric substrates in vitro. OsAOS1 converts (9S)-hydroperoxyoctadecadienoic acid or (9S)-hydroperoxyoctadecatrienoic acid into the corresponding unstable allene oxides, which are non-enzymatically transformed into a 9alpha-ketol as the major product, and 13gamma-ketols and cyclopentenone derivatives as minor products
-
-
?
additional information
?
-
allene oxide synthase is a key cytochrome P450 enzyme in the oxylipin pathway leading to allene oxide synthase-derived jasmonates
-
-
?
additional information
?
-
-
allene oxide synthase is a key cytochrome P450 enzyme in the oxylipin pathway leading to allene oxide synthase-derived jasmonates
-
-
?
additional information
?
-
-
13-HPL and 9-HPL activities on oxylipins, traumatin derivatives, in different plant organs, overview
-
-
?
additional information
?
-
-
the native enzyme is completely unreactive with polyunsaturated fatty acids or their hydroxylated analogues. Mass spectrometric product analysis, overview
-
-
?
additional information
?
-
-
in case of hydroperoxide lyases the homolytic isomerization of fatty acid hydroperoxides leads to a short-lived hemiacetal, which spontaneously disintegrates into (Z)-3-hexenal and (9Z)-12-oxo-9-dodecenoic acid
-
-
?
additional information
?
-
-
overview on substrates, configurations and mechanism
-
-
?
additional information
?
-
analysis of hexanal, (Z)-3-hexenal, (E)-2-hexenal, and (Z)-3-hexen-1-ol levels by gas chromatography
-
-
?
additional information
?
-
reaction products are identified and quantified using HPLC chromatography and mass spectrometry, product specifities, overview
-
-
?
additional information
?
-
no activity with (9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
-
-
?
additional information
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reaction products are identified and quantified using HPLC chromatography and mass spectrometry, product specifities, overview. No activity with (9Z,11E,13S,15Z)-13-hydroperoxy-9,11,15-octadecatrienoic acid
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