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Information on EC 5.3.99.6 - allene-oxide cyclase and Organism(s) Arabidopsis thaliana and UniProt Accession Q93ZC5

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EC Tree
     5 Isomerases
         5.3 Intramolecular oxidoreductases
             5.3.99 Other intramolecular oxidoreductases
                5.3.99.6 allene-oxide cyclase
IUBMB Comments
Allene oxides formed by the action of EC 4.2.1.92 hydroperoxide dehydratase, are converted into cyclopentenone derivatives.
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This record set is specific for:
Arabidopsis thaliana
UNIPROT: Q93ZC5
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The taxonomic range for the selected organisms is: Arabidopsis thaliana
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
allene oxide cyclase, osaoc, pnaoc, aaaoc, allene-oxide cyclase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Allene oxide cyclase
allene oxide oxidase 3
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Cyclase, allene oxide
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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
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. Stereoselectivity results from steric restrictions to the necessary substrate isomerizations imposed by the protein environment
(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
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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
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
13(S)-hydroperoxy-9(Z),11(E),15(Z)-octadecatrienoic acid
cis-(+)-12-oxophytodienoic acid
show the reaction diagram
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93.9% of cis-(+)-12-oxophytodienoic acid
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?
(9Z)-(13S)-12,13-epoxyoctadeca-9,11,15-trienoate
(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
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
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
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
vernolic acid
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substrate analogue, competitive
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
isoforms AOC4
UniProt
Manually annotated by BRENDA team
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
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loss-of-function of isoform AOC3 renders plants more susceptible to nematode Meloidogyne javanica infection
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
AOC4_ARATH
254
0
27809
Swiss-Prot
Chloroplast (Reliability: 1)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
65000
gel filtration
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
trimer
3 * 26000, isoform AOC2
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
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PROTEIN VARIANTS
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
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
K152A/E80A
the mutant shows strongly reduced activity compared to the wild type enzyme
K152A/E80A/L53S
the mutant shows strongly reduced activity compared to the wild type enzyme
L27R
101.3% of wild-type activity, 92.8% yield of cis-(+)-12-oxophytodienoic acid
L53S
the mutant shows strongly reduced activity compared to the wild type enzyme
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
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
Ni-NTA column chromatography
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
isoform AOC3 is highly induced during nematode Meloidogyne javanica infection
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Hofmann, E.; Zerbe, P.; Schaller, F.
The crystal structure of Arabidopsis thaliana allene oxide cyclase: insights into the oxylipin cyclization reaction
Plant Cell
18
3201-3217
2006
Arabidopsis thaliana
Manually annotated by BRENDA team
Schaller, F.; Zerbe, P.; Reinbothe, S.; Reinbothe, C.; Hofmann, E.; Pollmann, S.
The allene oxide cyclase family of Arabidopsis thaliana: localization and cyclization
FEBS J.
275
2428-2441
2008
Arabidopsis thaliana (Q93ZC5), Arabidopsis thaliana (Q9LS01), Arabidopsis thaliana (Q9LS02), Arabidopsis thaliana (Q9LS03), Arabidopsis thaliana
Manually annotated by BRENDA team
Cho, K.B.; Lai, W.; Hamberg, M.; Raman, C.S.; Shaik, S.
The reaction mechanism of allene oxide synthase: interplay of theoretical QM/MM calculations and experimental investigations
Arch. Biochem. Biophys.
507
14-25
2011
Arabidopsis thaliana
Manually annotated by BRENDA team
Naor, N.; Gurung, F.; Ozalvo, R.; Bucki, P.; Sanadhya, P.; Miyara, S.
Tight regulation of allene oxide synthase (AOS) and allene oxide cyclase-3 (AOC3) promote Arabidopsis susceptibility to the root-knot nematode Meloidogyne javanica
Eur. J. Plant Pathol.
150
149-165
2018
Arabidopsis thaliana
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Manually annotated by BRENDA team
otto, m.; naumann, c.; brandt, w.; wasternack, c.; hause, b.
activity regulation by heteromerization of Arabidopsis allene oxide cyclase family members
Plants (Basel)
5
pii: E3
2016
Arabidopsis thaliana (Q9LS02), Arabidopsis thaliana
Manually annotated by BRENDA team