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Information on EC 1.14.13.168 - indole-3-pyruvate monooxygenase
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EC Tree
1.14.13.168 indole-3-pyruvate monooxygenaseIUBMB 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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Word Map
- 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 expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
+
+
+
=
+
+
+
Synonyms
yucca6, yucca1, yucca2, yucca4, indole-3-pyruvate monooxygenase, yuc10, yuc11, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
spi1
-
-
-
-
YUC2
YUC3
YUC6
YUCCA
YUCCA2
YUC2
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
(indol-3-yl)pyruvate + NADPH + H+ + O2 = (indol-3-yl)acetate + NADP+ + H2O + CO2
-
-
-
-
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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.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
phenylpyruvate + NADPH + H+ + O2
phenylacetate + NADP+ + H2O + CO2
isoform YUC6 shows basal NADPH oxidase activity in the absence of the cosubstrate phenylpyruvate
-
-
?
(indol-3-yl)pyruvate + NADPH + H+ + O2
(indol-3-yl)acetate + NADP+ + H2O + CO2
-
-
-
?
(indol-3-yl)pyruvate + NADPH + H+ + O2
(indol-3-yl)acetate + NADP+ + H2O + CO2
-
-
-
-
?
(indol-3-yl)pyruvate + NADPH + H+ + O2
(indol-3-yl)acetate + NADP+ + H2O + CO2
-
-
-
-
ir
(indol-3-yl)pyruvate + NADPH + H+ + O2
(indol-3-yl)acetate + NADP+ + H2O + CO2
-
-
-
?
(indol-3-yl)pyruvate + NADPH + H+ + O2
(indol-3-yl)acetate + NADP+ + H2O + CO2
-
-
-
?
(indol-3-yl)pyruvate + NADPH + H+ + O2
(indol-3-yl)acetate + NADP+ + H2O + CO2
-
first step of the YUC6-catalyzed reaction is the reduction of the FAD cofactor to FADH- by NADPH. Subsequently, FADH- reacts with oxygen to form a flavin-C4a-(hydro)peroxy intermediate, which has a maximum absorbance at 381 nm in its UV-visible spectrum. The final chemical step is the reaction of the C4a-intermediate with (indol-3-yl)pyruvate to produce (indol-3-yl)acetate. The YUC6 intermediate has a half-life of about 20 s
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
(indol-3-yl)pyruvate + NADPH + H+ + O2
(indol-3-yl)acetate + NADP+ + H2O + CO2
-
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
FAD
-
required, binds at the big domain site in isoform YUC2. FAD is close to the nucleotide-binding motif Gly19, Ala20, Gly21, Pro22, Ser23, and Gly24, located in the first strand-turn-helix motif at the core of the big domain
NADPH
-
required, binds at the small domain site in isoform YUC2. NADPH cofactor is bound to the second nucleotide-binding motif, Gly188, Cys189, Gly190, Asn191, Ser192, and Gly193, which is located at the strand-turn-helix motif within the small domain
additional information
isoform YUC6 does not accept FMN as cofactor
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
indole-3-pyruvic acid
-
binds very close to FAD along the big domain, and yucasin competes for the same site as indole pyruvic acid, blocking indole acetic acid production
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
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
ponalrestat suppresses the native auxin signal and protects a GST-YUC2 fusion protein from Pronase degradation. Ponalrestat has an inhibitory effect on YUC2 protein, fits into the active site pocket of YUC2 and may act as a substrate antagonist. Treatment suppresses root hair formation and interrupts root gravitropic growth; ponalrestat suppresses the native auxin signal. Treatment suppresses root hair formation and interrupts root gravitropic growth
yucasin
-
in isoform YUC2, yucasin competes for the same site as indole pyruvic acid, blocking indole acetic acid production
-
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
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
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
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
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
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
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
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
physiological function
-
isoforms YUC1, YUC2, YUC4, YUC6 are the main enzymes for auxin biosynthesis in shoots and YUC3, YUC5, YUC7, YUC8, YUC9 are responsible for producing auxin in roots
physiological function
the enzyme catalyzes a rate-limiting step in auxin biosynthesis and is essential for many developmental processes
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
physiological function
-
10 members of the YUC gene family are found in Coffea canephora. The YUC enzymes require the prosthetic group FAD and the cofactor NADPH for their enzymatic activity. Indole-3-pyruvic acid binds very close to FAD along the big domain
physiological function
a quintuple mutant, with mutations in isoforms YUC3, YUC5, YUC7, YUC8, and YUC9, lost sensitivity to both the negative effects of ethylene precursor ACC and the positive effects of ponalrestat in root elongation
physiological function
upon seed-specific expression, YUC10.3 is expressed in a large amount in young seeds of the transgenic lines. The auxin content of the transgenic lines is significantly increased compared with controls. The variable importance in projection (VIP) of tryptophan reduces in the transgenic lines, while the VIP of indole acetic acid increases. The precursor amino acids for synthesizing some proteins and carbohydrates are upregulated in the transgenic lines, and the protein content of the seeds of the transgenic YUC10.3 wheat is significantly higher than that of the control. The wet gluten content and sedimentation value of the transgenic TaYUC10.3 wheat are also high
physiological function
-
YUC11 is a key contributor to auxin biosynthesis in rice endosperm. Grain filling or storage product accumulation is halted by mutation of YUC11, the deficiencies can be recovered by the exogenous application of auxin. YUC11 mutants exhibit reduced seed size and increased chalkiness, accompanied by a reduction in indole-3-acetic acid biosynthesis. Transcription factor NF-YB1 can bind the YUC11 promoter to induce gene expression in vivo
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). YUC10_ARATH
383
0
42387
Swiss-Prot
other Location (Reliability: 4)
YUC11_ARATH
391
0
43358
Swiss-Prot
Secretory Pathway (Reliability: 3)
YUC1_ARATH
414
0
46018
Swiss-Prot
other Location (Reliability: 4)
YUC1_ORYSJ
406
1
44388
Swiss-Prot
other Location (Reliability: 3)
YUC2_ARATH
415
0
46543
Swiss-Prot
other Location (Reliability: 2)
YUC3_ARATH
437
1
48747
Swiss-Prot
other Location (Reliability: 2)
YUC4_ARATH
411
0
45406
Swiss-Prot
other Location (Reliability: 4)
YUC4_ORYSJ
439
0
48202
Swiss-Prot
other Location (Reliability: 2)
YUC5_ARATH
424
1
47442
Swiss-Prot
other Location (Reliability: 4)
YUC6_ARATH
417
0
46638
Swiss-Prot
other Location (Reliability: 2)
YUC7_ARATH
431
0
48148
Swiss-Prot
Chloroplast (Reliability: 4)
YUC8_ARATH
426
0
48110
Swiss-Prot
other Location (Reliability: 3)
YUC8_ORYSI
421
0
45720
Swiss-Prot
other Location (Reliability: 3)
YUC8_ORYSJ
421
0
45720
Swiss-Prot
other Location (Reliability: 3)
YUC9_ARATH
421
0
47402
Swiss-Prot
other Location (Reliability: 4)
A0A2G9GD56_9LAMI
414
0
46068
TrEMBL
other Location (Reliability: 3)
A0A2P6PWE8_ROSCH
381
0
42743
TrEMBL
Secretory Pathway (Reliability: 5)
A0A2P6RLB4_ROSCH
108
0
11994
TrEMBL
other Location (Reliability: 3)
A0A5B6YQS8_DAVIN
412
0
45571
TrEMBL
Chloroplast (Reliability: 5)
A0A396I6R1_MEDTR
194
0
22045
TrEMBL
Secretory Pathway (Reliability: 4)
A0A2P6PTX6_ROSCH
85
0
9734
TrEMBL
other Location (Reliability: 2)
A0A2G9GNC0_9LAMI
381
0
42852
TrEMBL
other Location (Reliability: 4)
A0A0F8DDU6_CERFI
574
0
63182
TrEMBL
other Location (Reliability: 3)
A0A396IZ34_MEDTR
119
0
13789
TrEMBL
other Location (Reliability: 4)
A0A2G9GQW2_9LAMI
367
0
40857
TrEMBL
Secretory Pathway (Reliability: 4)
A0A396IW42_MEDTR
47
0
5065
TrEMBL
other Location (Reliability: 5)
A0A072U3V7_MEDTR
383
0
43202
TrEMBL
other Location (Reliability: 4)
A0A2P6Q680_ROSCH
108
0
12070
TrEMBL
other Location (Reliability: 3)
A0A5B6YR93_DAVIN
444
0
49216
TrEMBL
Mitochondrion (Reliability: 4)
A0A5B6YT21_DAVIN
124
0
14262
TrEMBL
other Location (Reliability: 2)
A0A2P6R2W3_ROSCH
377
0
42357
TrEMBL
other Location (Reliability: 4)
X5M7M3_9HYPH
452
0
49700
TrEMBL
-
A0A2P6PQZ0_ROSCH
381
0
42591
TrEMBL
other Location (Reliability: 5)
A0A2P6REW6_ROSCH
384
0
43326
TrEMBL
other Location (Reliability: 4)
A0A2P6QXM1_ROSCH
166
0
18664
TrEMBL
other Location (Reliability: 3)
A0A2P6PR20_ROSCH
167
0
18519
TrEMBL
Secretory Pathway (Reliability: 2)
G7JYZ1_MEDTR
382
0
42872
TrEMBL
Secretory Pathway (Reliability: 5)
A0A2P6PR05_ROSCH
201
0
23077
TrEMBL
other Location (Reliability: 5)
A0A3Q8Q0G2_PEA
220
0
24470
TrEMBL
other Location (Reliability: 4)
A0A2P6S0W1_ROSCH
112
0
13174
TrEMBL
Mitochondrion (Reliability: 3)
A0A5B7A8I4_DAVIN
150
0
16587
TrEMBL
Mitochondrion (Reliability: 5)
A0A396H400_MEDTR
41
0
4876
TrEMBL
other Location (Reliability: 2)
A0A5B6YT43_DAVIN
205
0
22536
TrEMBL
other Location (Reliability: 1)
A0A5B7CAL1_DAVIN
180
0
19804
TrEMBL
other Location (Reliability: 2)
A0A2G9GIV5_9LAMI
410
0
45601
TrEMBL
other Location (Reliability: 2)
A0A088DN37_WHEAT
382
0
42067
TrEMBL
other Location (Reliability: 3)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
molecular docking of FAD, NADPH, indole pyruvic acid, and yucasin to isoform YUC2. Indole pyruvic acid is located near the flavin of the prosthetic group FAD close to the small domain
-
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene YUC2, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)
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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)
brenda
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
brenda
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
brenda
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
brenda
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)
brenda
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)
brenda
Yang, Y.; Li, N.; Hui, W.; Yuan, B.; Fan, P.; Liu, J.; Wang, H.; Feng, D.
Seed-specific expression of TaYUC10 significantly increases auxin and protein content in wheat seeds
Plant Cell Rep.
40
301-314
2021
Triticum aestivum (A0A088DN37)
brenda
Xu, X.; E, Z.; Zhang, D.; Yun, Q.; Zhou, Y.; Niu, B.; Chen, C.
OsYUC11-mediated auxin biosynthesis is essential for endosperm development of rice
Plant Physiol.
185
934-950
2021
Oryza sativa
brenda
Uc-Chuc, M.A.; Ku-Gonzalez, A.F.; Jimenez-Ramirez, I.A.; Loyola-Vargas, V.M.
Identification, analysis, and modeling of the YUCCA protein family genome-wide in Coffea canephora
Proteins
90
1005-1024
2022
Coffea canephora
brenda
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Release 2023.1 (January 2023)
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