Information on EC 5.3.99.6 - allene-oxide cyclase

Word Map on EC 5.3.99.6
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)

The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
5.3.99.6
-
RECOMMENDED NAME
GeneOntology No.
allene-oxide cyclase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(9Z)-(13S)-12,13-epoxyoctadeca-9,11,15-trienoate = (15Z)-12-oxophyto-10,15-dienoate
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
intramolecular oxidoreduction
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
alpha-Linolenic acid metabolism
-
-
Biosynthesis of secondary metabolites
-
-
jasmonic acid biosynthesis
-
-
Metabolic pathways
-
-
SYSTEMATIC NAME
IUBMB Comments
(9Z)-(13S)-12,13-Epoxyoctadeca-9,11,15-trienoate isomerase (cyclizing)
Allene oxides formed by the action of EC 4.2.1.92 hydroperoxide dehydratase, are converted into cyclopentenone derivatives.
CAS REGISTRY NUMBER
COMMENTARY hide
118390-59-3
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
L., yellow onion, low activity
-
-
Manually annotated by BRENDA team
var. capitata, white cabbage
-
-
Manually annotated by BRENDA team
L., cucumber
-
-
Manually annotated by BRENDA team
pumpkin
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
GenBank
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
L., lettuce
-
-
Manually annotated by BRENDA team
L., eggplant
-
-
Manually annotated by BRENDA team
spinach
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
physiological function
Q8L6H4
the rice allene oxide cyclase functions in defence against blast fungus Magnaporthe oryzae through the pathway of jasmonate production
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(12,13S)-epoxy-(9Z,11,15Z)-octadecatrienoic acid
(9S,13S)-12-oxo-(10,15Z)-phytodienoic acid
show the reaction diagram
(12,13S)-epoxy-(9Z,11E,15Z)-octadecatrienoic acid
12-oxo-phytodienoic acid
show the reaction diagram
-
-
-
-
?
(12S)-hydroperoxy eicosatetraenoic acid
11-oxoprostatrienoic acid
show the reaction diagram
20:4(n-6)-derived (12S)-hydroperoxy eicosatetraenoic acid
-
-
?
(12Z)-9,10-epoxy-10,12-octadecadienoic acid
rac-cis-10-oxo-11-phytoenoic acid
show the reaction diagram
-
CYP74C3 catalyzes the synthesis, hydrolysis and cyclization of allene oxide
in addition, formation of some alpha-ketol
-
?
(5Z,8Z,10Z)-10-[3-[(2Z)-oct-2-en-1-yl]oxiran-2-ylidene]deca-5,8-dienoic acid
(5Z,14Z)-11-oxoprosta-5,9,14-trien-1-oic acid
show the reaction diagram
-
substrate for isoenzyme PpAOC2
-
-
?
(9Z)-(13S)-12,13-epoxyoctadeca-9,11,15-trienoate
(15Z)-12-oxophyto-10,15-dienoate
show the reaction diagram
(9Z,11E)-11-[(3S)-3-[(2Z)-pent-2-en-1-yl]oxiran-2-ylidene]undec-9-enoic acid
8-[(1R,5S)-4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl]octanoic acid
show the reaction diagram
-
-
i.e. cis-(+)-OPDA
-
?
(9Z,13S,15Z)-12,13-epoxy-9,11,15-octadecatrienoic acid
(9S,13S)-12-oxo-phytodienoic acid
show the reaction diagram
-
-
-
-
?
(9Z,13S,15Z)-12,13-epoxyoctadeca-9,11,15-trienoate
(9S,13S,15Z)-12-oxophyto-10,15-dienoate
show the reaction diagram
13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoic acid
cis-(+)-12-oxophytodienoic acid
show the reaction diagram
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(9Z)-(13S)-12,13-epoxyoctadeca-9,11,15-trienoate
(15Z)-12-oxophyto-10,15-dienoate
show the reaction diagram
(9Z,13S,15Z)-12,13-epoxy-9,11,15-octadecatrienoic acid
(9S,13S)-12-oxo-phytodienoic acid
show the reaction diagram
-
-
-
-
?
(9Z,13S,15Z)-12,13-epoxyoctadeca-9,11,15-trienoate
(9S,13S,15Z)-12-oxophyto-10,15-dienoate
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Cu2+
-
significantly enhances expression
additional information
-
wounding results in increased expression
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+/-)-cis-12,13-epoxy-(9Z)-octadecenoic acid
-
-
(+/-)-cis-9,10-Epoxy-(12Z)-octadecenoic acid
-
little effect
cis-12,13-Epoxy-(9Z,15Z)-octadecadienoic acid
-
-
vernolic acid
-
substrate analogue, competitive
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
jasmonic acid
-
induction of enzyme expression
theobroxide
-
additional information
mRNA expression is induced by salt stress and low temperature, 300 mM NaCl, 4°C
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7
Q8L6H4
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
Q8L6H4
assay at
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.58
calculated, DNA without putative chloroplast targeting signal
6.19
theoretical, without putative chloroplast signal peptide
6.24
theoretical
8.7
-
calculated
8.9
theoretical
8.99
calculated, full length DNA
9.1
-
calculated from amino acid sequence
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
highest mRNA expression
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
-
very low activity
Manually annotated by BRENDA team
-
embryo, very low activity
Manually annotated by BRENDA team
-
allene oxide cyclase is present in epidermal, cortical and pith parenchymic cells showing the highest levels in vascular tissues surrounding cells
Manually annotated by BRENDA team
-
allene oxide cyclase is present in epidermal, cortical and pith parenchymic cells showing the highest levels in vascular tissues surrounding cells
Manually annotated by BRENDA team
lowest expression level
Manually annotated by BRENDA team
-
green fruit, 38 days post anthesis, hila plus testae
Manually annotated by BRENDA team
-
allene oxide cyclase is present in epidermal, cortical and pith parenchymic cells showing the highest levels in vascular tissues surrounding cells
Manually annotated by BRENDA team
-
developing stolon, allene oxide cyclase and lipoxygenase are clearly detectable and levels do not change during development. Jasmonic acid treatment for 24 h increases protein levels of both enzymes. Both are present in the apex and along the stolon axis. Allene oxide cyclase is present in epidermal, cortical and pith parenchymic cells showing the highest levels in vascular tissues surrounding cells
Manually annotated by BRENDA team
-
allene oxide cyclase is present in epidermal, cortical and pith parenchymic cells showing the highest levels in vascular tissues surrounding cells
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20600
-
x * 20600, calculated from amino acid sequence
20660
theoretical, without putative chloroplast signal peptide
20700
theoretical
21000
recombinant protein, determined by SDS-PAGE and Western blot analysis
23000
-
x * 23000, SDS-PAGE
25890
x * 25890, calculated, x * 26000, SDS-PAGE
26000
x * 25890, calculated, x * 26000, SDS-PAGE
26160
theoretical
26610
-
x * 26610, calculated from amino acid sequence
26800
-
x * 26800, calculated
27000
determined by SDS-PAGE, His-tagged protein
33000
-
x * 33000, calculated from amino acid sequence; x * 33000, SDS-PAGE
45000
-
Zea mays, gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
modeling of complexes with substrate 12,13-epoxy-9,11,15-octadecatrienoic acid and product 12-oxo-phytodienoic acid. Reaction is promoted by anchimeric assistance through a conserved Glu residue. The transition state with a pentadienyl carbocation and an oxyanion is stabilized by a strongly bound water molecule and favorable pi-pi interactions with aromatic residues in the cavity
-
purified recombinant free isozyme AOC2, X-ray diffraction structure determination and analysis at 1.95 A resolution; purified recombinant isozyme AOC1, free or in complex with substrate analogue 12,13S-epoxy-9Z,15Z-octadecadienoic acid, X-ray diffraction structure determination and analysis at 1.35-2.0 A resolution
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Ni-NTA agarose column chromatography
-
on a Ni-NTA column
recombinant GST-tagged OsAOC lacking the chloroplast transit peptide from Escherichia coli strain BL21 by glutathione affinity chromatography
Q8L6H4
recombinant N-terminally GST-tagged isozyme AOC1 from Escherichia coli by glutathione affinity chromatography and gel filtration; recombinant N-terminally GST-tagged isozyme AOC1 from Escherichia coli by glutathione affinity chromatography and gel filtration
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
AOC1, expression as N-terminally GST-tagged enzyme in Escherichia coli; AOC2, expression as N-terminally GST-tagged enzyme in Escherichia coli
cloning of the promoter of AaAOC, the key gene of jasmonate biosynthetic pathway, expression analysis, AaAOC gene overexpression under control of the 35S promoter in Artemisia annua leading to an increase of 1.6 to 5.2fold in enzyme expression and 2 to 4.7fold increase in jasmonate levels, as well as to a significant increase of contents of artemisinin, dihydroartemisinic acid and artemisinic acid, expression analysis by RT-Q-PCR
-
expressed in Escherichia coli M15 cells
-
expressed in Escherichia coli SG13009 pRep4 cells
-
gene OsAOC, OsAOC lacking the chloroplast transit peptide is amplified from cultivar Nihonmasari cDNA and expressed as GST-tagged enzyme in Escherichia coli strain BL21
Q8L6H4
generating of a jasmonic acid-deficient rice line with suppressed expression of the genes encoding AOC with resistance to Magnaporthe grisea by introduction into rice plants by Agrobacterium-mediated transformation, the expression of AOC is induced after jasmonic acid and wound treatment, AOC-interfering RNA plants show normal resistance to both an incompatible and a compatible race of Magnaporthe grisea
Q8L6H4
into the vector pGEM-T Easy for sequencing and subsequently into the vector pQE30 for expression in Escherichia coli M15 cells
into the vector pMD18-T and for expression in Escherichia coli BL21DE3 cells subsequently into the vector pET-30a
transfection into tobacco via Agrobacterium tumefaciens
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
C71A
97.7% of wild-type activity, 94.1% yield of cis-(+)-12-oxophytodienoic acid
C71S
97.1% of wild-type activity, 93.9% yield of cis-(+)-12-oxophytodienoic acid
C71Y
33.3% of wild-type activity, 67.4% yield of cis-(+)-12-oxophytodienoic acid
E23A
29% of wild-type activity, 57.6% yield of cis-(+)-12-oxophytodienoic acid; complete loss of activity
F43Y
90.4% of wild-type activity, 93.5% yield of cis-(+)-12-oxophytodienoic acid
F51A
128.4% of wild-type activity, 94.7% yield of cis-(+)-12-oxophytodienoic acid
F85A
54.7% of wild-type activity, 71.7% yield of cis-(+)-12-oxophytodienoic acid
F85L
79.6% of wild-type activity, 87.7% yield of cis-(+)-12-oxophytodienoic acid
L27R
101.3% of wild-type activity, 92.8% yield of cis-(+)-12-oxophytodienoic acid
N25L
38.6% of wild-type activity, 63.4% yield of cis-(+)-12-oxophytodienoic acid
N53L
248% of wild-type activity, 83.4% yield of cis-(+)-12-oxophytodienoic acid
P32V
61% of wild-type activity, 57.1% yield of cis-(+)-12-oxophytodienoic acid
S31A
75.8% of wild-type activity, 71.8% yield of cis-(+)-12-oxophytodienoic acid
S31A/N53L
93.6% of wild-type activity, 84.9% yield of cis-(+)-12-oxophytodienoic acid
V49F
130.4% of wild-type activity, 93.0% yield of cis-(+)-12-oxophytodienoic acid
F140V
site-directed mutagenesis, the mutant variant is active with the 13-hydroperoxy octadecatrienoic acid-derived allene oxide, but inactive with 20:4(n-6)-derived (12S)-hydroperoxy eicosatetraenoic acid and (12S)-hydroperoxy eicosatetraenoic acid-derived allene oxide
F29I/F140V
site-directed mutagenesis, the mutant variant is active with the 13-hydroperoxy octadecatrienoic acid-derived allene oxide, but inactive with 20:4(n-6)-derived (12S)-hydroperoxy eicosatetraenoic acid and (12S)-hydroperoxy eicosatetraenoic acid-derived allene oxide
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
agriculture
biotechnology
-
constitutive overexpression of enzyme, 53fold increase of 12-oxo-phytodienoic acid methyl ester in stamen, 51fold increase of jasmonic acid in buds and 7.5fold increase in sepals. Increase in jasmonates and octadecanoids is accompanied by decreased levels of free lipid hydro(per)oxy compounds