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Information on EC 1.14.99.B1 - campesterol 22-hydroxylase
for references in articles please use BRENDA:EC1.14.99.B1preliminary BRENDA-supplied EC number
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EC Tree
1.14.99.B1 campesterol 22-hydroxylaseSpecify your search results
Word Map
- 1.14.99.B1
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brassinosteroids
- brassinazole
- brassinolide
- auxin
- hypocotyls
-
br-deficient
- campestanol
- dwarfism
- agriculture
The enzyme appears in viruses and cellular organisms
Synonyms
AOD4, C-22 hydroxylase, CYP724B2, CYP90B1, CYP90B3, DWARF4, Dwf4, steroid 22-hydroxylase, steroid 22-monooxygenase, 
more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
Dwf4
steroid 22-hydroxylase
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steroid 22-monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
campesterol + AH2 + O2 = 22alpha-hydroxycampesterol + A + H2O
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SYSTEMATIC NAME
IUBMB Comments
campesterol,hydrogen donor:oxygen oxidoreductase (22-hydroxylating)
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CAS REGISTRY NUMBER
COMMENTARY
83380-86-3
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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
(24R)-ergost-4-en-3-one + NADPH + H+ + O2
(22S,24R)-22-hydroxy-ergost-4-en-3-one + NADP+ + H2O
campestanol + NADPH + H+ + O2
6-deoxocathasterone + NADP+ + H2O
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catalytic efficiency for campesterol is 325 times greater than for campestanol. 17% of the activity with cholesterol
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?
campesterol + NADPH + H+ + O2
(22S)-22-hydroxycampesterol + NADP+ + H2O
best substrate
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campesterol + NADPH + H+ + O2
22alpha-hydroxycampesterol + NADP+ + H2O
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catalytic efficiency for campesterol is 325 times greater than for campestanol. 76.9% of the activity with cholesterol
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cholestanol + NADPH + H+ + O2
22-hydroxy-cholestanol + NADP+ + H2O
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29% of the activity with cholesterol
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?
cholesterol + NADPH + H+ + O2
22-hydroxy-cholesterol + NADP+ + H2O
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sitosterol + NADPH + H+ + O2
22-hydroxy-sitosterol + NADP+ + H2O
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poor substrate. 10.7% of the activity with cholesterol
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?
(24R)-ergost-4-en-3-one + NADPH + H+ + O2
(22S,24R)-22-hydroxy-ergost-4-en-3-one + NADP+ + H2O
17% of the activity with campesterol
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?
(24R)-ergost-4-en-3-one + NADPH + H+ + O2
(22S,24R)-22-hydroxy-ergost-4-en-3-one + NADP+ + H2O
7.9% of the activity with campesterol
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additional information
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substrates with a double bond at positions C5 and C6 are preferred substrates
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additional information
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Arabidopsis plants ectopically overexpressing DWF4 (AOD4) are generated, using the cauliflower mosaic virus 35S promoter, and their phenotypes are characterized. The hypocotyl length of both light and dark-grown AOD4 seedlings is increased dramatically as compared to wild type. At maturity, inflorescence height increases >35% in AOD4 lines and >14% in tobacco DWF4 overexpressing lines (TOD4), relative to controls. The total number of branches and siliques increased more than twofold in AOD4 plants, leading to a 59% increase in the number of seeds produced
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additional information
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DWF4 is down-regulated by jasmonate and is located downstream of COI1 in the jasmonate-signaling pathway
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?
additional information
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only 22alpha-hydroxylated brassinosteroids rescue the dwf4 phenotype, confirming that DWF4 acts as a 22alpha-hydroxylase
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additional information
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the 22-hydroxylation step is one of the rate-limiting steps in brassinosteroid biosynthesis
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?
additional information
?
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the regulation of DWARF4 expression is likely a critical mechanism in maintaining the homeostasis of bioactive brassinosteroids in Arabidopsis
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?
additional information
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CYP724B2 function in the early steps of C-22 hydroxylation of brassinosteroid biosynthesis
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additional information
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CYP724B2 function in the early steps of C-22 hydroxylation of brassinosteroid biosynthesis
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additional information
?
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CYP724B2 function in the early steps of C-22 hydroxylation of brassinosteroid biosynthesis
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additional information
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the enzyme catalyzes C-22 hydroxylation of (14R)-5alpha-ergostan-3-one and campestanol at a trace level
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additional information
?
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the enzyme catalyzes C-22 hydroxylation of (14R)-5alpha-ergostan-3-one and campestanol at a trace level
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additional information
?
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the enzyme catalyzes C-22 hydroxylation of (14R)-5alpha-ergostan-3-one and campestanol at a trace level
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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
additional information
?
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Arabidopsis plants ectopically overexpressing DWF4 (AOD4) are generated, using the cauliflower mosaic virus 35S promoter, and their phenotypes are characterized. The hypocotyl length of both light and dark-grown AOD4 seedlings is increased dramatically as compared to wild type. At maturity, inflorescence height increases >35% in AOD4 lines and >14% in tobacco DWF4 overexpressing lines (TOD4), relative to controls. The total number of branches and siliques increased more than twofold in AOD4 plants, leading to a 59% increase in the number of seeds produced
-
-
?
additional information
?
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DWF4 is down-regulated by jasmonate and is located downstream of COI1 in the jasmonate-signaling pathway
-
-
?
additional information
?
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only 22alpha-hydroxylated brassinosteroids rescue the dwf4 phenotype, confirming that DWF4 acts as a 22alpha-hydroxylase
-
-
?
additional information
?
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the 22-hydroxylation step is one of the rate-limiting steps in brassinosteroid biosynthesis
-
-
?
additional information
?
-
the regulation of DWARF4 expression is likely a critical mechanism in maintaining the homeostasis of bioactive brassinosteroids in Arabidopsis
-
-
?
additional information
?
-
CYP724B2 function in the early steps of C-22 hydroxylation of brassinosteroid biosynthesis
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-
?
additional information
?
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CYP724B2 function in the early steps of C-22 hydroxylation of brassinosteroid biosynthesis
-
-
?
additional information
?
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CYP724B2 function in the early steps of C-22 hydroxylation of brassinosteroid biosynthesis
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?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(2RS,4RS)-1-[4-propyl-2-(4-trifluoromethylphenyl)-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole
DWF4 is the target site of Brz220 in Arabidopsis. Arabidopsis thaliana treated with 2RS,4RS-1-[4-propyl-2-(4-trifluoromethylphenyl)-1,3-dioxane-2-ylmethyl]-1H-1,2,4-triazole shows a dwarf phenotype
bitertanol
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i.e. 2,3,3-trimethyl-1-biphenyl4-yloxy-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, Kd value is 0.0467 mM
brassinazole
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addition of brassinazole to the DWF4 protein induces a type II absorbance shift of the heme Soret band from 416 to 421 nm indicative of direct coordination of the triazole group of the brassinazole to the heme iron of DWF4. Kd value for brassinazole is 0.000001 M
Brz117
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i.e. 4-(3-methoxyphenyl)-2-phenyl-3-(1H-1,2,4-triazol-1-yl)butan-2-ol, Kd value is 0.0117 mM
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Dwarfism
Arabidopsis NAC transcription factor JUB1 regulates GA/BR metabolism and signalling.
Dwarfism
Arabidopsis thaliana RALF1 opposes brassinosteroid effects on root cell elongation and lateral root formation.
Infertility, Male
Arabidopsis NAC transcription factor JUB1 regulates GA/BR metabolism and signalling.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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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
DWF4 expression is highest in apical shoots, and high in siliques. The expression of DWF4 in roots is comparable with that in shoots
brenda
transcript in mature fruit and in immature fruit
brenda
transcript in mature fruit, no transcript detected in immature fruit
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DWF4 transcripts accumulate in the actively growing tissues, such as root, shoot apices with floral clusters, joint tissues of root and shoot, and dark-grown seedlings
brenda
DWF4 expression is highest in apical shoots, and high in siliques. The expression of DWF4 in roots is comparable with that in shoots
brenda
DWF4 transcripts accumulate in the actively growing tissues, such as root, shoot apices with floral clusters, joint tissues of root and shoot, and dark-grown seedlings
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
the expression of DWARF4, which encodes a C-22 hydroxylase, is crucial for brassinosteroid biosynthesis and for the feedback control of endogenous brassinosteroid levels. The amount of the DWF4 mRNA precursor either decreases or increases, similarly with its mature form, in response to an exogenously applied bioactive brassinosteroid, brassinolide, and a brassinosteroid biosynthesis inhibitor, brassinazole, respectively. Brassinosteroids act positively on root elongation under the control of auxin
physiological function
the expression of DWARF4, which encodes a C-22 hydroxylase, is crucial for brassinosteroid biosynthesis and for the feedback control of endogenous brassinosteroid levels. DWF4 transcription plays an important role in the brassinosteroid-auxin crosstalk associated with root elongation, in addition to its role in brassinosteroid homeostasis
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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). Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
construction of DWF4::GUS plants, enzyme expression patterns in response to brassinazole and brassinolide in roots, overview
additional information
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construction of DWF4::GUS plants, enzyme expression patterns in response to brassinazole and brassinolide in roots, overview
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
Arabidopsis plants ectopically overexpressing DWF4 (AOD4) are generated, using the cauliflower mosaic virus 35S promoter, and their phenotypes are characterized. The hypocotyl length of both light and dark-grown AOD4 seedlings is increased dramatically as compared to wild type. At maturity, inflorescence height increases >35% in AOD4 lines and >14% in tobacco DWF4 overexpressing lines (TOD4), relative to controls. The total number of branches and siliques increased more than twofold in AOD4 plants, leading to a 59% increase in the number of seeds produced
expression in insect cell using a baculovirus expression system
gene DWF4, semi-quantitative reverse-transcriptase PCR expression analysis
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
downregulation of enzyme expression by brassinosteroid biosynthesis inhibitor brassinazole
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
agriculture
it will be possible to control plant growth by engineering DWF4 transcription in plants
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Ohnishi, T.; Watanabe, B.; Sakata, K.; Mizutani, M.
CYP724B2 and CYP90B3 function in the early C-22 hydroxylation steps of brassinosteroid biosynthetic pathway in tomato
Biosci. Biotechnol. Biochem.
70
2071-2080
2006
Solanum lycopersicum (A0ZS62), Solanum lycopersicum (A0ZS63), Solanum lycopersicum
brenda
Asami, T.; Mizutani, M.; Fujioka, S.; Goda, H.; Min, Y.K.; Shimada, Y.; Nakano, T.; Takatsuto, S.; Matsuyama, T.; Nagata, N.; Sakata, K.; Yoshida, S.
Selective interaction of triazole derivatives with DWF4, a cytochrome P450 monooxygenase of the brassinosteroid biosynthetic pathway, correlates with brassinosteroid deficiency in planta
J. Biol. Chem.
276
25687-25691
2001
Arabidopsis thaliana
brenda
Kappler, C.; Kabbouh, M.; Hetru, C.; Durst, F.; Hoffmann, J.A.
Characterization of three hydroxylases involved in the final steps of biosynthesis of the steroid hormone ecdysone in Locusta migratoria (Insecta, Orthoptera)
J. Steroid Biochem.
31
891-898
1988
Locusta migratoria
brenda
Fujita, S.; Ohnishi, T.; Watanabe, B.; Yokota, T.; Takatsuto, S.; Fujioka, S.; Yoshida, S.; Sakata, K.; Mizutani, M.
Arabidopsis CYP90B1 catalyses the early C-22 hydroxylation of C27, C28 and C29 sterols
Plant J.
45
765-774
2006
Arabidopsis thaliana
brenda
Sekimata, K.; Ohnishi, T.; Mizutani, M.; Todoroki, Y.; Han, S.Y.; Uzawa, J.; Fujioka, S.; Yoneyama, K.; Takeuchi, Y.; Takatsuto, S.; Sakata, K.; Yoshida, S.; Asami, T.
Brz220 interacts with DWF4, a cytochrome P450 monooxygenase in brassinosteroid biosynthesis, and exerts biological activity
Biosci. Biotechnol. Biochem.
72
7-12
2008
Arabidopsis thaliana (O64989), Arabidopsis thaliana
brenda
Choe, S.; Dilkes, B.P.; Fujioka, S.; Takatsuto, S.; Sakurai, A.; Feldmann, K.A.
The DWF4 gene of Arabidopsis encodes a cytochrome P450 that mediates multiple 22alpha-hydroxylation steps in brassinosteroid biosynthesis
Plant Cell
10
231-243
1998
Arabidopsis thaliana (O64989)
brenda
Choe, S.; Fujioka, S.; Noguchi, T.; Takatsuto, S.; Yoshida, S.; Feldmann, K.A.
Overexpression of DWARF4 in the brassinosteroid biosynthetic pathway results in increased vegetative growth and seed yield in Arabidopsis
Plant J.
26
573-582
2001
Arabidopsis thaliana (O64989)
brenda
Shimada, Y.; Goda, H.; Nakamura, A.; Takatsuto, S.; Fujioka, S.; Yoshida, S.
Organ-specific expression of brassinosteroid-biosynthetic genes and distribution of endogenous brassinosteroids in Arabidopsis
Plant Physiol.
131
287-297
2003
Arabidopsis thaliana (O64989)
brenda
Kim, H.B.; Kwon, M.; Ryu, H.; Fujioka. S.; Takatsuto, S.; Yoshida, S.; An, C.S.; Lee, I.; Hwang, I.; Choe, S.
The regulation of DWARF4 expression is likely a critical mechanism in maintaining the homeostasis of bioactive brassinosteroids in Arabidopsis
Plant Physiol.
140
548-557
2006
Arabidopsis thaliana (O64989)
brenda
Ren, C.; Han, C.; Peng, W.; Huang, Y.; Peng, Z.; Xiong, X.; Zhu, Q.; Gao, B.; Xie, D.
A leaky mutation in DWARF4 reveals an antagonistic role of brassinosteroid in the inhibition of root growth by jasmonate in Arabidopsis
Plant Physiol.
151
1412-1420
2009
Arabidopsis thaliana (O64989)
brenda
Yoshimitsu, Y.; Tanaka, K.; Fukuda, W.; Asami, T.; Yoshida, S.; Hayashi, K.; Kamiya, Y.; Jikumaru, Y.; Shigeta, T.; Nakamura, Y.; Matsuo, T.; Okamoto, S.
Transcription of DWARF4 plays a crucial role in auxin-regulated root elongation in addition to brassinosteroid homeostasis in Arabidopsis thaliana
PLoS ONE
6
e23851
2011
Arabidopsis thaliana (O64989), Arabidopsis thaliana
brenda
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