Information on EC 1.14.13.168 - indole-3-pyruvate monooxygenase

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The expected taxonomic range for this enzyme is: Arabidopsis thaliana

EC NUMBER
COMMENTARY hide
1.14.13.168
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RECOMMENDED NAME
GeneOntology No.
indole-3-pyruvate monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(indol-3-yl)pyruvate + NADPH + H+ + O2 = (indol-3-yl)acetate + NADP+ + H2O + CO2
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
indole-3-acetate biosynthesis I
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indole-3-acetate biosynthesis II
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Tryptophan metabolism
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Metabolic pathways
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SYSTEMATIC NAME
IUBMB Comments
indole-3-pyruvate,NADPH:oxygen oxidoreductase (1-hydroxylating, decarboxylating)
This plant enzyme, along with EC 2.6.1.99 L-tryptophan---pyruvate aminotransferase, is responsible for the biosynthesis of the plant hormone indole-3-acetate from L-tryptophan.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
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a single YUC gene in Arabidopsis does not cause obvious developmental defects, but simultaneous disruption of several YUC genes in Arabidopsis leads to defects in embryogenesis, seedling growth, flower development, and vascular pattern
metabolism
YUCCA, a flavin-containing monooxygenase (YUC), catalyzes the last step of conversion from indole-3-pyruvate to indole-3-acetic acid
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(indol-3-yl)pyruvate + NADPH + H+ + O2
(indol-3-yl)acetate + NADP+ + H2O + CO2
show the reaction diagram
phenylpyruvate + NADPH + H+ + O2
phenylacetate + NADP+ + H2O + CO2
show the reaction diagram
isoform YUC6 shows basal NADPH oxidase activity in the absence of the cosubstrate phenylpyruvate
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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
(indol-3-yl)pyruvate + NADPH + H+ + O2
(indol-3-yl)acetate + NADP+ + H2O + CO2
show the reaction diagram
Q9SVQ1
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
isoform YUC6 does not accept FMN as cofactor
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-chlorophenylboronic acid
moderate inhibition of enzyme activity and primary root elongation. Probably unspecific inhibition
3,5-dibromophenylboronic acid
probably unspecific inhibition, inhibits root hair formation in wild-type Arabidopsis thaliana seedlings
3,5-dichlorophenylboronic acid
probably unspecific inhibition, inhibits root hair formation in wild-type Arabidopsis thaliana seedlings
3-chlorophenylboronic acid
probably unspecific inhibition, strongly inhibits root hair formation in wild-type Arabidopsis thaliana seedlings
4-biphenylboronic acid
BBo, competitive, inhibits the activity of recombinant YUC in vitro, reduces endogenous indole-3-acetic acid content, and strongly inhibits primary root elongation and lateral root formation in wild-type Arabidopsis thaliana seedlings
4-chlorophenylboronic acid
probably unspecific inhibition, strongly inhibits root hair formation in wild-type Arabidopsis thaliana seedlings
4-methyl-4-biphenylboronic acid
weak inhibition of enzyme activity, but strong inhibition of primary root elongation
4-phenoxyphenylboronic acid
PPBo, competitive, inhibits the activity of recombinant YUC in vitro, reduces endogenous indole-3-acetic acid content, and strongly inhibits primary root elongation and lateral root formation in wild-type Arabidopsis thaliana seedlings. The compound does not interfere with the auxin response of auxin-marker genes when it was co-treated with indole acetic acid, suggesting that PPBo is not an inhibitor of auxin sensing or signaling
phenethylboronic acid
moderate inhibition of enzyme activity and primary root elongation
phenylboronic acid
PBo, inhibition of enzyme activity, but not of primary root elongation
additional information
FAD and boronic acid is not the main reason for inhibition of enzyme activity by boronic acid derivatives. Poor inhibition by 2,6-dichlorophenylboronic acid
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.026
NADPH
in the presence of phenylpyruvate, in 50 mM sodium phosphate, pH 8.0, 500 mM NaCl, and 30% (v/v) glycerol, at 25°C
0.043
phenylpyruvate
in the presence of NADPH, in 50 mM sodium phosphate, pH 8.0, 500 mM NaCl, and 30% (v/v) glycerol, at 25°C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.31
NADPH
in the presence of phenylpyruvate, in 50 mM sodium phosphate, pH 8.0, 500 mM NaCl, and 30% (v/v) glycerol, at 25°C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.000067
4-biphenylboronic acid
pH 8.5, 35°C, recombinant His-tagged enzyme
0.000056
4-phenoxyphenylboronic acid
pH 8.5, 35°C, recombinant His-tagged enzyme
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
48000
x * 48000, isoform YUC6, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 48000, isoform YUC6, SDS-PAGE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expession in Escherichia coli; expressed in Escherichia coli BL21 Star (DE3) cells
expressed in Escherichia coli
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gene YUC2, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)