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Literature summary for 1.14.13.168 extracted from

  • Kakei, Y.; Yamazaki, C.; Suzuki, M.; Nakamura, A.; Sato, A.; Ishida, Y.; Kikuchi, R.; Higashi, S.; Kokudo, Y.; Ishii, T.; Soeno, K.; Shimada, Y.
    Small-molecule auxin inhibitors that target YUCCA are powerful tools for studying auxin function (2015), Plant J., 84, 827-837 .
    View publication on PubMed

Cloned(Commentary)

Cloned (Comment) Organism
gene YUC2, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3) Arabidopsis thaliana

Inhibitors

Inhibitors Comment 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 Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
(indol-3-yl)pyruvate + NADPH + H+ + O2 Arabidopsis thaliana
-
(indol-3-yl)acetate + NADP+ + H2O + CO2
-
?

Organism

Organism UniProt Comment Textmining
Arabidopsis thaliana Q9SVQ1
-
-

Purification (Commentary)

Purification (Comment) Organism
recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography Arabidopsis thaliana

Source Tissue

Source Tissue Comment Organism Textmining
seedling
-
Arabidopsis thaliana
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(indol-3-yl)pyruvate + NADPH + H+ + O2
-
Arabidopsis thaliana (indol-3-yl)acetate + NADP+ + H2O + CO2
-
?

Synonyms

Synonyms Comment 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] Comment Organism
35
-
assay at Arabidopsis thaliana

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
8.5
-
assay at Arabidopsis thaliana

Cofactor

Cofactor Comment Organism Structure
FAD
-
Arabidopsis thaliana
NADPH
-
Arabidopsis thaliana

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment 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

General Information

General Information Comment 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