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Information on EC 1.14.13.168 - indole-3-pyruvate monooxygenase and Organism(s) Arabidopsis thaliana and UniProt Accession Q8VZ59

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EC Tree
IUBMB Comments
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.
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This record set is specific for:
Arabidopsis thaliana
UNIPROT: Q8VZ59
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Word Map
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  • 1.14.13.168
  • auxin
  • iaa
  • indole-3-acetic
  • one-hybrid
  • high-auxin
  • gynoecium
  • tryptophan-dependent
  • auxin-response
  • auxin-related
  • dark-induced
  • dr5::gus
  • parthenocarpy
The taxonomic range for the selected organisms is: Arabidopsis thaliana
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
yucca6, yucca1, yucca2, yucca4, indole-3-pyruvate monooxygenase, yuc10, yuc11, more
PATHWAY SOURCE
PATHWAYS
-
-, -
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.
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
(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
-
-
?
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
(indol-3-yl)pyruvate + NADPH + H+ + O2
(indol-3-yl)acetate + NADP+ + H2O + CO2
show the reaction diagram
-
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
-
INHIBITOR
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
ponalrestat
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
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
-
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
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
YUC6_ARATH
417
0
46638
Swiss-Prot
other Location (Reliability: 2)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
48000
x * 48000, isoform YUC6, SDS-PAGE
SUBUNIT
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
-
expressed in Escherichia coli BL21 Star (DE3) cells
gene YUC2, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Dai, X.; Mashiguchi, K.; Chen, Q.; Kasahara, H.; Kamiya, Y.; Ojha, S.; Dubois, J.; Ballou, D.; Zhao, Y.
The biochemical mechanism of auxin biosynthesis by an Arabidopsis YUCCA flavin-containing monooxygenase
J. Biol. Chem.
288
1448-1457
2013
Arabidopsis thaliana, Arabidopsis thaliana (Q8VZ59)
Manually annotated by BRENDA team
Zhao, Y.
Auxin biosynthesis: A simple two-step pathway converts tryptophan to indole-3-acetic acid in plants
Mol. Plant
5
334-338
2012
Arabidopsis thaliana
Manually annotated by BRENDA team
Stepanova, A.; Yun, J.; Robles, L.; Novak, O.; He, W.; Guo, H.; Ljung, K.; Alonso, J.
The Arabidopsis YUCCA1 flavin monooxygenase functions in the indole-3-pyruvic acid branch of auxin biosynthesis
Plant Cell
23
3961-3973
2011
Arabidopsis thaliana (Q8VZ59), Arabidopsis thaliana (Q9LFM5), Arabidopsis thaliana (Q9SVQ1), Arabidopsis thaliana (Q9SZY8), Arabidopsis thaliana
Manually annotated by BRENDA team
Mashiguchi, K.; Tanaka, K.; Sakai, T.; Sugawara, S.; Kawaide, H.; Natsume, M.; Hanada, A.; Yaeno, T.; Shirasu, K.; Yao, H.; McSteen, P.; Zhao, Y.; Hayashi, K.; Kamiya, Y.; Kasahara, H.
The main auxin biosynthesis pathway in Arabidopsis
Proc. Natl. Acad. Sci. USA
108
18512-18517
2011
Arabidopsis thaliana
Manually annotated by BRENDA team
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
Plant J.
84
827-837
2015
Arabidopsis thaliana (Q9SVQ1)
Manually annotated by BRENDA team
Zhu, Y.; Li, H.J.; Su, Q.; Wen, J.; Wang, Y.; Song, W.; Xie, Y.; He, W.; Yang, Z.; Jiang, K.; Guo, H.
A phenotype-directed chemical screen identifies ponalrestat as an inhibitor of the plant flavin monooxygenase YUCCA in auxin biosynthesis
J. Biol. Chem.
294
19923-19933
2019
Arabidopsis thaliana (O23024), Arabidopsis thaliana (Q9SVQ1)
Manually annotated by BRENDA team