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Information on EC 1.14.14.86 - ent-kaurene monooxygenase and Organism(s) Oryza sativa and UniProt Accession Q5Z5R4

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IUBMB Comments
A cytochrome P-450 (heme thiolate) protein found in plants. Catalyses three successive oxidations of the 4-methyl group of ent-kaurene giving kaurenoic acid.
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This record set is specific for:
Oryza sativa
UNIPROT: Q5Z5R4
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The taxonomic range for the selected organisms is: Oryza sativa
The enzyme appears in selected viruses and cellular organisms
Synonyms
ent-kaurene oxidase, kaurene oxidase, osko2, p450-4, cyp701b1, cyp701a, cyp701a26, psko1, cyp701, cyp701a6, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ent-kaurene oxidase-like protein
Q68YV8
-
KOS3
Q68YV8
-
CYP701A
-
-
CYP701A6
-
-
ent-kaurene oxidase
-
-
OsKO
-
-
OsKO2
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formerly named OsKOL2, OsKO1 expression is restricted to panicles and roots
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
redox reaction
-
-
-
-
oxidation
-
-
-
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reduction
-
-
-
-
SYSTEMATIC NAME
IUBMB Comments
ent-kaur-16-ene,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (hydroxylating)
A cytochrome P-450 (heme thiolate) protein found in plants. Catalyses three successive oxidations of the 4-methyl group of ent-kaurene giving kaurenoic acid.
CAS REGISTRY NUMBER
COMMENTARY hide
149565-67-3
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(-)-kaurene + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
(-)-kaurenoic acid + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
show the reaction diagram
ent-kaur-16-en-19-al + [reduced NADPH-hemoprotein reductase] + O2
ent-kaur-16-en-19-oate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
three step oxidation process via ent-kaurenol and ent-kaurenal, in co-operation with membrane-associated cytochrome P450 monooxygenase
-
-
?
ent-kaur-16-en-19-ol + [reduced NADPH-hemoprotein reductase] + O2
ent-kaur-16-en-19-al + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
ent-kaur-16-ene + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
ent-kaur-16-en-19-oate + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
show the reaction diagram
-
-
-
-
?
ent-kaur-16-ene + [reduced NADPH-hemoprotein reductase] + O2
ent-kaur-16-en-19-ol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
ent-kaur-16-ene-19-al + [reduced NADPH-hemoprotein reductase] + O2
ent-kaur-16-en-19-oic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
ent-kaur-16-ene-19-ol + [reduced NADPH-hemoprotein reductase] + O2
ent-kaur-16-en-19-al + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
-
-
-
-
?
ent-kaurene + [reduced NADPH-hemoprotein reductase] + O2
(-)-kaurenoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
additional information
?
-
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
(-)-kaurene + 3 [reduced NADPH-hemoprotein reductase] + 3 O2
(-)-kaurenoic acid + 3 [oxidized NADPH-hemoprotein reductase] + 4 H2O
show the reaction diagram
Q68YV8
the enzyme plays a key role in the biosynthesis of plant growth hormones gibberellins
-
-
?
ent-kaur-16-en-19-al + [reduced NADPH-hemoprotein reductase] + O2
ent-kaur-16-en-19-oate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
three step oxidation process via ent-kaurenol and ent-kaurenal, in co-operation with membrane-associated cytochrome P450 monooxygenase
-
-
?
ent-kaur-16-en-19-ol + [reduced NADPH-hemoprotein reductase] + O2
ent-kaur-16-en-19-al + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
-
-
-
-
?
ent-kaur-16-ene + [reduced NADPH-hemoprotein reductase] + O2
ent-kaur-16-en-19-ol + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
ent-kaur-16-ene-19-al + [reduced NADPH-hemoprotein reductase] + O2
ent-kaur-16-en-19-oic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
ent-kaur-16-ene-19-ol + [reduced NADPH-hemoprotein reductase] + O2
ent-kaur-16-en-19-al + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
-
-
-
-
?
ent-kaurene + [reduced NADPH-hemoprotein reductase] + O2
(-)-kaurenoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
-
?
additional information
?
-
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(E)-2-(2-((1-(4-(3-hydroxy-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-1-yl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)ethoxy)ethyl 4-methylbenzenesulfonate
-
i.e. abscinazole-E1, orUT1-E2Ts, or Abz-E1, a specific potent inhibitor of ABA 8'-hydroxylase, EC 1.14.13.93, but a weak inhibitor of CYP701A, both in vitro and in vivo
abscinazole-F1
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-
DSI-505ME
-
-
uniconazole
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i.e. UNI
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450 monooxygenase
-
necessary for ent-kaurenoate production by ent-kaurene oxidase
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00097
(E)-2-(2-((1-(4-(3-hydroxy-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-1-yl)phenyl)-1H-1,2,3-triazol-4-yl)methoxy)ethoxy)ethyl 4-methylbenzenesulfonate
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pH 7.25, 30°C, recombinant enzyme
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
Q68YV8
gibberellic acid content in healthy and rice dwarf virus-infected plants
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.25
-
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
Q68YV8
-
Manually annotated by BRENDA team
-
sheat
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
membrane associated
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
-
function in the early steps of gibberellin biosynthesis
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
70000
-
Western blot analysis
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant CYP701A partially from insect Sf9 cells in microsomes
-
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
KOS3, DNA and amino acid sequence determination and analysis, sequence comparisons
Q68YV8
CYP701A, expression in Spodoptera frugiperda Sf9 cells using the baculovirus transfection method
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expressed in Escherichia coli BL21(DE3) cells
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PCR-amplification of cDNA, cloning into pPICZ yeast expression vector, expression in Pichia pastoris strain X-33 together with fungal P450 reductase (CPR)
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
biotechnology
Q68YV8
P2 may provide a tool to investigate the regulation of GA metabolism for plant growth and development via affection of ent-kaurene oxidase
molecular biology
-
the fungal cytochrome P450 monooxygenase isolated from from Phaeoshaeria sp., strain L487 in the Pichia pastoris expression system might become a tool for functional assays of a variety of rice cytochrome P450 monooxygenases involved in the biosynthesis of secondary metabolites
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Sakamoto, T.; Miura, K.; Itoh, H.; Tatsumi, T.; Ueguchi-Tanaka, M.; Ishiyama, K.; Kobayashi, M.; Agrawal, G.K.; Takeda, S.; Abe, K.; Miyao, A.; Hirochika, H.; Kitano, H.; Ashikari, M.; Matsuoka, M.
An overview of gibberellin metabolism enzyme genes and their related mutants in rice
Plant Physiol.
134
1642-1653
2004
Oryza sativa
Manually annotated by BRENDA team
Zhu, S.; Gao, F.; Cao, X.; Chen, M.; Ye, G.; Wei, C.; Li, Y.
The rice dwarf virus P2 protein interacts with ent-kaurene oxidases in vivo, leading to reduced biosynthesis of gibberellins and rice dwarf symptoms
Plant Physiol.
139
1935-1945
2005
Oryza sativa (Q68YV8), Oryza sativa Japonica Group (Q68YV7), Oryza sativa Japonica Group (Q68YV9), Oryza sativa Japonica Group (Q6GZ42)
Manually annotated by BRENDA team
Ko, K.W.; Lin, F.; Katsumata, T.; Sugai, Y.; Miyazaki, S.; Kawaide, H.; Okada, K.; Nojiri, H.; Yamane, H.
Functional identification of a rice ent-kaurene oxidase, OsKO2, using the Pichia pastoris expression system
Biosci. Biotechnol. Biochem.
72
3285-3288
2008
Oryza sativa
Manually annotated by BRENDA team
Okazaki, M.; Nimitkeatkai, H.; Muramatsu, T.; Aoyama, H.; Ueno, K.; Mizutani, M.; Hirai, N.; Kondo, S.; Ohnishi, T.; Todoroki, Y.
Abscinazole-E1, a novel chemical tool for exploring the role of ABA 8-hydroxylase CYP707A
Bioorg. Med. Chem.
19
406-413
2011
Oryza sativa, Oryza sativa Nipponbare
Manually annotated by BRENDA team
Wang, Q.; Hillwig, M.L.; Wu, Y.; Peters, R.J.
CYP701A8: a rice ent-kaurene oxidase paralog diverted to more specialized diterpenoid metabolism
Plant Physiol.
158
1418-1425
2012
Oryza sativa
Manually annotated by BRENDA team