Information on EC 1.14.14.45 - aromatic aldoxime N-monooxygenase

for references in articles please use BRENDA:EC1.14.14.45
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Select one or more organisms in this record:

The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.14.14.45
-
RECOMMENDED NAME
GeneOntology No.
aromatic aldoxime N-monooxygenase
-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(E)-indol-3-ylacetaldehyde oxime + [reduced NADPH-hemoprotein reductase] + glutathione + O2 = S-[(E)-N-hydroxy(indol-3-yl)acetimidoyl]-L-glutathione + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
(1), overall reaction
-
-
-
(E)-indol-3-ylacetaldehyde oxime + [reduced NADPH-hemoprotein reductase] + O2 = 1-(1H-indol-3-yl)-2-aci-nitroethane + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(1a)
-
-
-
(E)-phenylacetaldehyde oxime + [reduced NADPH-hemoprotein reductase] + glutathione + O2 = S-[(Z)-N-hydroxy(phenyl)acetimidoyl]-L-glutathione + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
(2), overall reaction
-
-
-
(E)-phenylacetaldehyde oxime + [reduced NADPH-hemoprotein reductase] + O2 = 1-aci-nitro-2-phenylethane + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(2a)
-
-
-
1-(1H-indol-3-yl)-2-aci-nitroethane + glutathione = S-[(E)-N-hydroxy(indol-3-yl)acetimidoyl]-L-glutathione + H2O
show the reaction diagram
(1b), spontaneous
-
-
-
1-aci-nitro-2-phenylethane + glutathione = S-[(Z)-N-hydroxy(phenyl)acetimidoyl]-L-glutathione + H2O
show the reaction diagram
(2b), spontaneous
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Tryptophan metabolism
-
-
Glucosinolate biosynthesis
-
-
Biosynthesis of secondary metabolites
-
-
SYSTEMATIC NAME
IUBMB Comments
(E)-indol-3-ylacetaldoxime,[reduced NADPH—hemoprotein reductase],glutathione:oxygen oxidoreductase (oxime-hydroxylating)
This cytochrome P-450 (heme thiolate) enzyme is involved in the biosynthesis of glucosinolates in plants. The enzyme catalyses the N-hydroxylation of aromatic aldoximes derived from L-tryptophan, L-phenylalanine, and L-tyrosine, forming an aci-nitro intermediate that reacts non-enzymically with glutathione to produce an N-alkyl-thiohydroximate adduct, the committed precursor of glucosinolates. In the absence of glutathione, the enzyme is suicidal, probably due to interaction of the reactive aci-nitro compound with catalytic residues in the active site.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
B6VC79
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(E)-4-hydroxyphenylacetaldoxime + O2 + [reduced NADPH-hemoprotein reductase]
1-aci-nitro-2-(4-hydroxyphenyl)-ethane + H2O + [oxidized NADPH-hemoprotein reductase]
show the reaction diagram
-
-
-
-
?
(E)-indol-3-ylacetaldehyde oxime + [reduced NADPH-hemoprotein reductase] + glutathione + O2
S-[(E)-N-hydroxy(indol-3-yl)acetimidoyl]-L-glutathione + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
-
-
overall reaction
-
?
(E)-p-hydroxyphenylacetaldehyde oxime + [reduced NADPH-hemoprotein reductase] + glutathione + O2
S-[(Z)-N-hydroxy(p-hydroxyphenyl)acetimidoyl]-L-glutathione + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
-
-
overall reaction
-
?
(E)-p-hydroxyphenylacetaldoxime + NADPH + H+ + 2-mercaptoethanol
(Z)-2-hydroxyethyl N,4-dihydroxybenzene-1-carboximidothioate + NADP+ + H2O
show the reaction diagram
-
CYP83B1 shows absolute specificity towards (E)-p-hydroxyphenylacetaldoxime as a substrate, and the (Z)-S-alkyl-thiohydroximate formed maintains the structural configuration of the oxime function as in the (E)-p-hydroxyphenylacetaldoxime substrate
-
?
(E)-phenylacetaldehyde oxime + [reduced NADPH-hemoprotein reductase] + glutathione + O2
S-[(Z)-N-hydroxy(phenyl)acetimidoyl]-L-glutathione + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
-
-
overall reaction
-
?
(E)-phenylacetaldoxime + O2 + [reduced NADPH-hemoprotein reductase]
1-aci-nitro-2-phenylethane + H2O + [oxidized NADPH-hemoprotein reductase]
show the reaction diagram
-
-
-
-
?
1-aci-nitro-2-(4-hydroxyphenyl)-ethane + 2-mercaptoethanol
(Z)-2-hydroxyethyl N-hydroxy-2-(4-hydroxyphenyl)ethanimidothioate + H2O
show the reaction diagram
-
-
-
-
?
an (E)-omega-(methylthio)alkanal oxime + O2 + glutathione + [reduced NADPH-hemoprotein reductase]
an (E)-1-(glutathione-S-yl)-omega-(methylthio)alkylhydroximate + 2 H2O + [oxidized NADPH-hemoprotein reductase]
show the reaction diagram
-
-
-
-
?
indole-3-acetaldoxime + O2 + glutathione + [reduced NADPH-hemoprotein reductase]
1-aci-nitro-2-indolyl-ethane + H2O + [oxidized NADPH-hemoprotein reductase]
show the reaction diagram
indole-3-acetaldoxime + [reduced NADPH-hemoprotein reductase] + O2
1-aci-nitro-2-indolyl-ethane + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
-
-
the aci-nitro compound formed reacts non-enzymatically with thiol compounds to produce an N-alkyl-thiohydroximate adduct, the committed precursor of glucosinolates
-
?
p-hydroxyphenylacetaldoxime + [reduced NADPH-hemoprotein reductase] + cysteine + O2
S-(benzohydroximoyl)-L-cysteine + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
-
-
overall reaction
-
?
p-hydroxyphenylacetaldoxime + [reduced NADPH-hemoprotein reductase] + N-acetylcysteine + O2
S-(benzohydroximoyl)-N-acetyl-L-cysteine + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
-
-
overall reaction
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
(E)-4-hydroxyphenylacetaldoxime + O2 + [reduced NADPH-hemoprotein reductase]
1-aci-nitro-2-(4-hydroxyphenyl)-ethane + H2O + [oxidized NADPH-hemoprotein reductase]
show the reaction diagram
-
-
-
-
?
(E)-indol-3-ylacetaldehyde oxime + [reduced NADPH-hemoprotein reductase] + glutathione + O2
S-[(E)-N-hydroxy(indol-3-yl)acetimidoyl]-L-glutathione + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
-
-
overall reaction
-
?
(E)-p-hydroxyphenylacetaldehyde oxime + [reduced NADPH-hemoprotein reductase] + glutathione + O2
S-[(Z)-N-hydroxy(p-hydroxyphenyl)acetimidoyl]-L-glutathione + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
-
-
overall reaction
-
?
(E)-phenylacetaldehyde oxime + [reduced NADPH-hemoprotein reductase] + glutathione + O2
S-[(Z)-N-hydroxy(phenyl)acetimidoyl]-L-glutathione + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
-
-
overall reaction
-
?
1-aci-nitro-2-(4-hydroxyphenyl)-ethane + 2-mercaptoethanol
(Z)-2-hydroxyethyl N-hydroxy-2-(4-hydroxyphenyl)ethanimidothioate + H2O
show the reaction diagram
-
-
-
-
?
an (E)-omega-(methylthio)alkanal oxime + O2 + glutathione + [reduced NADPH-hemoprotein reductase]
an (E)-1-(glutathione-S-yl)-omega-(methylthio)alkylhydroximate + 2 H2O + [oxidized NADPH-hemoprotein reductase]
show the reaction diagram
-
-
-
-
?
indole-3-acetaldoxime + [reduced NADPH-hemoprotein reductase] + O2
1-aci-nitro-2-indolyl-ethane + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
-
-
the aci-nitro compound formed reacts non-enzymatically with thiol compounds to produce an N-alkyl-thiohydroximate adduct, the committed precursor of glucosinolates
-
?
additional information
?
-
-
CYP83B1 catalyzes the conversion of the (E)-p-hydroxyphenylacetaldoxime into an S-alkyl-thiohydroximate with retention of the configuration of the E-oxime intermediate in the final glucosinolate core structure. CYP83B1 from Arabidopsis thaliana cannot convert the (E)-p-hydroxyphenylacetaldoxime to the (Z)-isomer, which blocks the route towards cyanogenic glucoside synthesis
-
-
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
-
-
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
tryptamine
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0031
(E)-indol-3-ylacetaldehyde oxime
-
pH 8.1, 29°C
-
0.065
(E)-p-hydroxyphenylacetaldehyde oxime
-
pH 8.1, 29°C
-
0.188
(E)-phenylacetaldehyde oxime
-
pH 8.1, 29°C
0.003
indole-3-acetaldoxime
-
pH 7.6, 28°C
0.068
p-hydroxyphenylacetaldoxime
-
pH 81, 29°C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.43 - 0.87
(E)-indol-3-ylacetaldehyde oxime
-
0.16 - 0.23
(E)-p-hydroxyphenylacetaldehyde oxime
-
0.25 - 0.78
(E)-phenylacetaldehyde oxime
0.88 - 53
indole-3-acetaldoxime
0.27
p-hydroxyphenylacetaldoxime
-
pH 8.1, 29°C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
267
(E)-indol-3-ylacetaldehyde oxime
-
pH 8.1, 29°C
-
3.7
(E)-p-hydroxyphenylacetaldehyde oxime
-
pH 8.1, 29°C
-
4.2
(E)-phenylacetaldehyde oxime
-
pH 8.1, 29°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
B6VC79
high abundance in root
Manually annotated by BRENDA team
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
-
expression in Saccharomyces cerevisiae
-