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Enzyme Nomenclature
Information on EC 1.14.99.B1 - campesterol 22-hydroxylase
for references in articles please use BRENDA:EC1.14.99.B1
Word Map on EC 1.14.99.B1
- 1.14.99.B1
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brassinosteroids
- brassinolide
- brassinazole
- auxin
- hypocotyls
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br-deficient
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phytohormone
- dwarfism
- campestanol
- agriculture
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
1.14.99.B1
preliminary BRENDA-supplied EC number
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RECOMMENDED NAME
GeneOntology No.
campesterol 22-hydroxylase
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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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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
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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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 SUBSTRATES
NATURAL PRODUCTS
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
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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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O64989
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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A0ZS62
CYP724B2 function in the early steps of C-22 hydroxylation of brassinosteroid biosynthesis
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additional information
?
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A0ZS63
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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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITORS
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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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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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
transcript in mature fruit and in immature fruit; transcript in mature fruit, no transcript detected in immature fruit
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DWF4 expression is highest in apical shoots, and high in siliques. The expression of DWF4 in roots is comparable with that in shoots
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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
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DWF4 expression is highest in apical shoots, and high in siliques. The expression of DWF4 in roots is comparable with that in shoots
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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
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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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
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expression in insect cell using a baculovirus expression system; 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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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
construction of DWF4::GUS plants, enzyme expression patterns in response to brassinazole and brassinolide in roots, overview
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
agriculture
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it will be possible to control plant growth by engineering DWF4 transcription in plants
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.99.B1)
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