BRENDA - Enzyme Database
show all sequences of 1.14.13.168

Small-molecule auxin inhibitors that target YUCCA are powerful tools for studying auxin function

Kakei, Y.; Yamazaki, C.; Suzuki, M.; Nakamura, A.; Sato, A.; Ishida, Y.; Kikuchi, R.; Higashi, S.; Kokudo, Y.; Ishii, T.; Soeno, K.; Shimada, Y.; Plant J. 84, 827-837 (2015) View publication on PubMed

Data extracted from this reference:

Cloned(Commentary)
Cloned (Commentary)
Organism
gene YUC2, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)
Arabidopsis thaliana
Inhibitors
Inhibitors
Commentary
Organism
Structure
2-chlorophenylboronic acid
moderate inhibition of enzyme activity and primary root elongation. Probably unspecific inhibition
Arabidopsis thaliana
3,5-dibromophenylboronic acid
probably unspecific inhibition, inhibits root hair formation in wild-type Arabidopsis thaliana seedlings
Arabidopsis thaliana
3,5-dichlorophenylboronic acid
probably unspecific inhibition, inhibits root hair formation in wild-type Arabidopsis thaliana seedlings
Arabidopsis thaliana
3-chlorophenylboronic acid
probably unspecific inhibition, strongly inhibits root hair formation in wild-type Arabidopsis thaliana seedlings
Arabidopsis thaliana
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
Arabidopsis thaliana
4-chlorophenylboronic acid
probably unspecific inhibition, strongly inhibits root hair formation in wild-type Arabidopsis thaliana seedlings
Arabidopsis thaliana
4-methyl-4-biphenylboronic acid
weak inhibition of enzyme activity, but strong inhibition of primary root elongation
Arabidopsis thaliana
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
Arabidopsis thaliana
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
Arabidopsis thaliana
phenethylboronic acid
moderate inhibition of enzyme activity and primary root elongation
Arabidopsis thaliana
phenylboronic acid
PBo, inhibition of enzyme activity, but not of primary root elongation
Arabidopsis thaliana
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
(indol-3-yl)pyruvate + NADPH + H+ + O2
Arabidopsis thaliana
-
(indol-3-yl)acetate + NADP+ + H2O + CO2
-
-
?
Organism
Organism
UniProt
Commentary
Textmining
Arabidopsis thaliana
Q9SVQ1
-
-
Purification (Commentary)
Purification (Commentary)
Organism
recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography
Arabidopsis thaliana
Source Tissue
Source Tissue
Commentary
Organism
Textmining
seedling
-
Arabidopsis thaliana
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
Substrate Product ID
(indol-3-yl)pyruvate + NADPH + H+ + O2
-
746081
Arabidopsis thaliana
(indol-3-yl)acetate + NADP+ + H2O + CO2
-
-
-
?
Synonyms
Synonyms
Commentary
Organism
flavin-containing monooxygenase YUC
-
Arabidopsis thaliana
YUC2
-
Arabidopsis thaliana
YUCCA
-
Arabidopsis thaliana
YUCCA2
-
Arabidopsis thaliana
Temperature Optimum [°C]
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
35
-
assay at
Arabidopsis thaliana
pH Optimum
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
8.5
-
assay at
Arabidopsis thaliana
Cofactor
Cofactor
Commentary
Organism
Structure
FAD
-
Arabidopsis thaliana
NADPH
-
Arabidopsis thaliana
Ki Value [mM]
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
0.000056
-
4-phenoxyphenylboronic acid
pH 8.5, 35°C, recombinant His-tagged enzyme
Arabidopsis thaliana
0.000067
-
4-biphenylboronic acid
pH 8.5, 35°C, recombinant His-tagged enzyme
Arabidopsis thaliana
Cloned(Commentary) (protein specific)
Commentary
Organism
gene YUC2, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)
Arabidopsis thaliana
Cofactor (protein specific)
Cofactor
Commentary
Organism
Structure
FAD
-
Arabidopsis thaliana
NADPH
-
Arabidopsis thaliana
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
2-chlorophenylboronic acid
moderate inhibition of enzyme activity and primary root elongation. Probably unspecific inhibition
Arabidopsis thaliana
3,5-dibromophenylboronic acid
probably unspecific inhibition, inhibits root hair formation in wild-type Arabidopsis thaliana seedlings
Arabidopsis thaliana
3,5-dichlorophenylboronic acid
probably unspecific inhibition, inhibits root hair formation in wild-type Arabidopsis thaliana seedlings
Arabidopsis thaliana
3-chlorophenylboronic acid
probably unspecific inhibition, strongly inhibits root hair formation in wild-type Arabidopsis thaliana seedlings
Arabidopsis thaliana
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
Arabidopsis thaliana
4-chlorophenylboronic acid
probably unspecific inhibition, strongly inhibits root hair formation in wild-type Arabidopsis thaliana seedlings
Arabidopsis thaliana
4-methyl-4-biphenylboronic acid
weak inhibition of enzyme activity, but strong inhibition of primary root elongation
Arabidopsis thaliana
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
Arabidopsis thaliana
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
Arabidopsis thaliana
phenethylboronic acid
moderate inhibition of enzyme activity and primary root elongation
Arabidopsis thaliana
phenylboronic acid
PBo, inhibition of enzyme activity, but not of primary root elongation
Arabidopsis thaliana
Ki Value [mM] (protein specific)
Ki Value [mM]
Ki Value maximum [mM]
Inhibitor
Commentary
Organism
Structure
0.000056
-
4-phenoxyphenylboronic acid
pH 8.5, 35°C, recombinant His-tagged enzyme
Arabidopsis thaliana
0.000067
-
4-biphenylboronic acid
pH 8.5, 35°C, recombinant His-tagged enzyme
Arabidopsis thaliana
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
(indol-3-yl)pyruvate + NADPH + H+ + O2
Arabidopsis thaliana
-
(indol-3-yl)acetate + NADP+ + H2O + CO2
-
-
?
Purification (Commentary) (protein specific)
Commentary
Organism
recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography
Arabidopsis thaliana
Source Tissue (protein specific)
Source Tissue
Commentary
Organism
Textmining
seedling
-
Arabidopsis thaliana
-
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
ID
(indol-3-yl)pyruvate + NADPH + H+ + O2
-
746081
Arabidopsis thaliana
(indol-3-yl)acetate + NADP+ + H2O + CO2
-
-
-
?
Temperature Optimum [°C] (protein specific)
Temperature Optimum [°C]
Temperature Optimum Maximum [°C]
Commentary
Organism
35
-
assay at
Arabidopsis thaliana
pH Optimum (protein specific)
pH Optimum Minimum
pH Optimum Maximum
Commentary
Organism
8.5
-
assay at
Arabidopsis thaliana
General Information
General Information
Commentary
Organism
metabolism
YUCCA, a flavin-containing monooxygenase (YUC), catalyzes the last step of conversion from indole-3-pyruvate to indole-3-acetic acid
Arabidopsis thaliana
physiological function
the enzyme catalzes the last step in the indole-3-pyruvate pathway, a major biosynthesis pathway in Arabidopsis thaliana for indole-3-acetic acid, the most common member of the auxin family
Arabidopsis thaliana
General Information (protein specific)
General Information
Commentary
Organism
metabolism
YUCCA, a flavin-containing monooxygenase (YUC), catalyzes the last step of conversion from indole-3-pyruvate to indole-3-acetic acid
Arabidopsis thaliana
physiological function
the enzyme catalzes the last step in the indole-3-pyruvate pathway, a major biosynthesis pathway in Arabidopsis thaliana for indole-3-acetic acid, the most common member of the auxin family
Arabidopsis thaliana
Other publictions for EC 1.14.13.168
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Synonyms
Temperature Optimum [°C]
Temperature Range [°C]
Temperature Stability [°C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [°C] (protein specific)
Temperature Range [°C] (protein specific)
Temperature Stability [°C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
746081
Kakei
Small-molecule auxin inhibito ...
Arabidopsis thaliana
Plant J.
84
827-837
2015
-
-
1
-
-
-
11
-
-
-
-
1
-
1
-
-
1
-
-
1
-
-
1
-
4
1
-
-
-
1
-
-
2
2
-
-
-
-
1
2
-
-
-
-
11
2
-
-
-
-
1
-
-
-
1
-
1
-
-
1
-
1
-
-
-
1
-
-
-
-
2
2
-
-
-
720064
Dai
The biochemical mechanism of a ...
Arabidopsis thaliana
J. Biol. Chem.
288
1448-1457
2013
-
-
2
-
-
-
-
2
-
-
1
-
-
2
-
-
-
-
-
-
-
-
3
1
4
-
-
-
1
-
-
-
3
-
-
-
-
-
2
3
-
-
-
-
-
-
2
-
-
1
-
-
-
-
-
-
-
-
-
3
1
-
-
-
1
-
-
-
-
-
1
1
-
-
-
720508
Zhao
Auxin biosynthesis: A simple t ...
Arabidopsis thaliana
Mol. Plant
5
334-338
2012
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
2
-
-
1
-
10
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
2
-
-
1
-
-
-
-
-
-
-
-
-
-
2
2
-
-
-
720688
Stepanova
The Arabidopsis YUCCA1 flavin ...
Arabidopsis thaliana
Plant Cell
23
3961-3973
2011
-
-
-
-
-
-
-
-
-
-
-
-
-
8
-
-
-
-
-
-
-
-
4
-
8
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
4
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
720921
Mashiguchi
The main auxin biosynthesis pa ...
Arabidopsis thaliana
Proc. Natl. Acad. Sci. USA
108
18512-18517
2011
-
-
1
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
1
-
3
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
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-
-