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Information on EC 4.2.1.92 - hydroperoxide dehydratase
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4.2.1.92 hydroperoxide dehydrataseIUBMB Comments
Acts on a number of unsaturated fatty-acid hydroperoxides, forming the corresponding allene oxides. The product of the above reaction is unstable and is acted upon by EC 5.3.99.6, allene-oxide cyclase, to form the cyclopentenone derivative (15Z)-12-oxophyto-10,15-dienoate (OPDA), which is the first cyclic and biologically active metabolite in the jasmonate biosynthesis pathway . The enzyme from many plants belongs to the CYP-74 family of P-450 monooxygenases .
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Word Map
- 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
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
allene oxide synthase, hydroperoxide lyase, cyp74, hydroperoxide isomerase, elox3, rubber particle protein, osaos1, fatty acid hydroperoxide lyase, oshpl3, hydroperoxide dehydrase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
13-HPL
13-hydroperoxide lyase
13-hydroperoxide-lyase
9R-DOX-AOS
9S-DOX-AOS
allene oxide synthase
AOS
CmHPL
CYP74
CYP74A
CYP74c
cytochrome P450 74A
-
-
-
-
EC 5.3.99.1
-
-
formerly
-
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
hydroperoxide dehydrase
-
-
-
-
hydroperoxide isomerase
hydroperoxide lyase
hydroperoxidehydrase
-
-
-
-
isomerase, hydroperoxide
-
-
-
-
KC525886
linoleate hydroperoxide isomerase
-
-
-
-
linoleic acid hydroperoxide isomerase
-
-
-
-
LOX
RPP
-
-
-
-
rubber particle protein
-
-
-
-
hydroperoxide isomerase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(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
mechanism
-
(9Z,11E,15Z)-(13S)-hydroperoxyoctadeca-9,11,15-trienoate = (9Z,15Z)-(13S)-12,13-epoxyoctadeca-9,11,15-trienoate + H2O
mechanism
-
(9Z,11E,15Z)-(13S)-hydroperoxyoctadeca-9,11,15-trienoate = (9Z,15Z)-(13S)-12,13-epoxyoctadeca-9,11,15-trienoate + H2O
mechanism
-
(9Z,11E,15Z)-(13S)-hydroperoxyoctadeca-9,11,15-trienoate = (9Z,15Z)-(13S)-12,13-epoxyoctadeca-9,11,15-trienoate + H2O
mechanism
-
(9Z,11E,15Z)-(13S)-hydroperoxyoctadeca-9,11,15-trienoate = (9Z,15Z)-(13S)-12,13-epoxyoctadeca-9,11,15-trienoate + H2O
acts on a number of unsaturated fatty-acid hydroperoxides, forming the corresponding allene oxides
-
-
-
(9Z,11E,15Z)-(13S)-hydroperoxyoctadeca-9,11,15-trienoate = (9Z,15Z)-(13S)-12,13-epoxyoctadeca-9,11,15-trienoate + H2O
reaction mechanisms of wild-type AOS and mutant F137L, QM/MM calculations, overview
-
(9Z,11E,15Z)-(13S)-hydroperoxyoctadeca-9,11,15-trienoate = (9Z,15Z)-(13S)-12,13-epoxyoctadeca-9,11,15-trienoate + H2O
mechanism
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
C-O bond cleavage by elimination of water
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
(9Z,11E,15Z)-(13S)-hydroperoxyoctadeca-9,11,15-trienoate 12,13-hydro-lyase [(9Z,15Z)-(13S)-12,13-epoxyoctadeca-9,11,15-trienoate-forming]
Acts on a number of unsaturated fatty-acid hydroperoxides, forming the corresponding allene oxides. The product of the above reaction is unstable and is acted upon by EC 5.3.99.6, allene-oxide cyclase, to form the cyclopentenone derivative (15Z)-12-oxophyto-10,15-dienoate (OPDA), which is the first cyclic and biologically active metabolite in the jasmonate biosynthesis pathway [3]. The enzyme from many plants belongs to the CYP-74 family of P-450 monooxygenases [4].
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CAS REGISTRY NUMBER
COMMENTARY
118390-60-6
-
37318-50-6
-
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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
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(9R)-hydroperoxy-(10E,12Z,15Z)-octadecatrienoic acid
9-hydroxy-10-oxo-(12Z,15Z)-octadecadienoic acid
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(9R)-hydroperoxy-(10E,12Z,15Z)-octadecatrienoic acid
9-hydroxy-10-oxo-(12Z,15Z)-octadecadienoic acid
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?
(9R,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid
(9R,10)-10-epoxy-(10Z,12Z)-octadecadienoic acid
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an unstable allene oxide
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?
(9R,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid
(9R,10)-10-epoxy-(10Z,12Z)-octadecadienoic acid
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an unstable allene oxide
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?
(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
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(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
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(9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid
10-oxo-(9R)-hydroxy-cis-12-octadecadienoic acid + H2O
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9-hydroxy-10-oxo,cis-12-octadecenoic acid and 13-hydroxy-10-oxo-trans-11-octadecenoic acid in the ratio 2:1
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(9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid
10-oxo-(9R)-hydroxy-cis-12-octadecadienoic acid + H2O
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(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
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(9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid
10-oxo-(9R)-hydroxy-cis-12-octadecadienoic acid + H2O
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(9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid
10-oxo-(9R)-hydroxy-cis-12-octadecadienoic acid + H2O
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?
(9S)-hydroperoxy-(10E,12Z)-octadecadienoic acid
10-oxo-(9R)-hydroxy-cis-12-octadecadienoic acid + H2O
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in presence of linoleate the product is (9R)-linoleoyloxy-10-oxo-cis-12-octadecenoic acid
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(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 + ?
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(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 + ?
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?
(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 + ?
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(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 + ?
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(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 + ?
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(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 + ?
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(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid
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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
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(9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoic acid
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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
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(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid
(9Z)-12-hydroxy-9-dodecenoic acid + ?
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(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid
(9Z)-12-hydroxy-9-dodecenoic acid + ?
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(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid
(9Z)-12-hydroxy-9-dodecenoic acid + ?
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(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid
9-hydroxynonanoic acid + (9Z)-12-hydroxy-9-dodecenoic acid + ?
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(9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid