Information on EC 1.14.13.140 - 2-hydroxy-1,4-benzoxazin-3-one monooxygenase

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The expected taxonomic range for this enzyme is: Zea mays

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EC NUMBER
COMMENTARY hide
1.14.13.140
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RECOMMENDED NAME
GeneOntology No.
2-hydroxy-1,4-benzoxazin-3-one monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
2-hydroxy-2H-1,4-benzoxazin-3(4H)-one + NAD(P)H + H+ + O2 = 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one + NAD(P)+ + H2O
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Benzoxazinoid biosynthesis
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Biosynthesis of secondary metabolites
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DIBOA-glucoside biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
2-hydroxy-2H-1,4-benzoxazin-3(4H)-one,NAD(P)H:oxygen oxidoreductase (N-hydroxylating)
The enzyme is involved in the biosynthesis of protective and allelophatic benzoxazinoids in some plants, most commonly from the family of Poaceae (grasses). It is a member of the cytochrome P-450 dependent monooxygenases.
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2-hydroxy-2H-1,4-benzoxazin-3(4H)-one + NADPH + H+ + O2
2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one + NADP+ + H2O
show the reaction diagram
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?
additional information
?
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no activity with NADH and FAD
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P-450
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dependent on
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cytochrome P450
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NADPH
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2,2'-dipyridyl
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5 mM inhibits activity by 57%
Ca2+
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5 mM Ca2+ inhibits activity by 69%
carbon monoxide
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the effect of carbon monoxide can be reversed by exposing the enzyme to 450 nanometer light during the incubation period
cytochrome c
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Fe2+
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5 mM Fe2+ inhibits activity by 64%
Hg2+
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complete inhibition at 5 mM
Mg2+
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5 mM Mg2+ inhibits activity by 45%
Mn2+
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complete inhibition at 5 mM
N-ethylmaleimide
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5 mM inhibits activity by 97%
N2
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the effect of nitrogen can be reversed by exposing the enzyme to air
NADP+
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NaN3
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5 mM NaN3 inhibits activity by 16%
p-chloromercuribenzoate
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5 mM inhibits activity by 58%
Zn2+
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complete inhibition at 5 mM
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
EDTA
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49% enhancement of activity at 5 mM
additional information
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not affected by 5 mM diethyldithiocarbamate
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.005 - 0.013
2-hydroxy-2H-1,4-benzoxazin-3(4H)-one
0.005
NADPH
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in 50 mM HEPES, pH 8.5, at 35°C
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00016
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recombinant enzyme, using 2-hydroxy-2H-1,4-benzoxazin-3(4H)-one as substrate, at pH 7.5 and 25°C
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5
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-
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
35
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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Manually annotated by BRENDA team
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
100
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heating the enzyme for 10 min at 100°C in a boiling water bath results in a total loss of activity
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
extraction of microsomes in the absence of dithioerythritol results in total loss of activity, but exclusion of dithioerythritol from the assay buffer has no effect on enzyme activity
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Saccharomyces cerevisiae strain WAT11 and in Escherichia coli strain BL21 (DE3)
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
CYP71C3 is 2.8fold induced in 2.5 day old naphthalic anhydride-treated seedling shoots, 2fold induced in 6.5 day old naphthalic anhydride-treated seedling shoots, and 5fold induced in 2.5 day old naphthalic anhydride/triasulfuron-treated seedling shoots. The pathogens Erwinia stuartii and Acidovorax avenae induce CYP71C3 transcript 1.9 and 2.7fold, respectively
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CYP71C3 transcripts are not induced in root tissues by either naphthalic anhydride or naphthalic anhydride/triasulfuron treatment
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.140)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
SYSTERS
Protein Mutant Database
InterPro (database of protein families, domains and functional sites)