Information on EC 1.14.14.44 - phenylacetaldehyde oxime monooxygenase

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The expected taxonomic range for this enzyme is: Prunus mume

EC NUMBER
COMMENTARY hide
1.14.14.44
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RECOMMENDED NAME
GeneOntology No.
phenylacetaldehyde oxime monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(E)-phenylacetaldehyde oxime + [reduced NADPH-hemoprotein reductase] + O2 = (R)-mandelonitrile + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
overall reaction
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(E)-phenylacetaldehyde oxime = (Z)-phenylacetaldehyde oxime
show the reaction diagram
(1a)
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(Z)-phenylacetaldehyde oxime = phenylacetonitrile + H2O
show the reaction diagram
(1b)
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phenylacetonitrile + [reduced NADPH-hemoprotein reductase] + O2 = (R)-mandelonitrile + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(1c)
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Cyanoamino acid metabolism
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
(E)-phenylacetaldehyde oxime,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase
This cytochrome P-450 (heme-thiolate) enzyme is involved in the biosynthesis of the cyanogenic glucosides (R)-prunasin and (R)-amygdalin. It catalyses three different activities - isomerization of the (E) isomer to the (Z) isomer, dehydration, and C-hydroxylation.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
var. Sieb. et Zucc.
UniProt
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(E)-phenylacetaldehyde oxime
(Z)-phenylacetaldehyde oxime
show the reaction diagram
-
-
-
?
(E)-phenylacetaldehyde oxime + [reduced NADPH-hemoprotein reductase] + O2
(R)-mandelonitrile + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
-
overall reaction
-
?
(Z)-phenylacetaldehyde oxime
phenylacetonitrile + H2O
show the reaction diagram
-
-
-
?
4-hydroxyphenylacetaldoxime + [reduced NADPH-hemoprotein reductase] + O2
hydroxy(4-hydroxyphenyl)acetonitrile + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
-
overall reaction
-
?
4-hydroxyphenylacetonitrile + [reduced NADPH-hemoprotein reductase] + O2
hydroxy(4-hydroxyphenyl)acetonitrile + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
-
-
-
?
indole-3-acetaldoxime + [reduced NADPH-hemoprotein reductase] + O2
hydroxy(1H-indol-3-yl)acetonitrile + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
reaction of EC 1.14.14.45
overall reaction
-
?
indole-3-acetonitrile + [reduced NADPH-hemoprotein reductase] + O2
hydroxy(1H-indol-3-yl)acetonitrile + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
reaction of EC 1.14.14.45
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-
?
phenylacetonitrile + [reduced NADPH-hemoprotein reductase] + O2
(R)-mandelonitrile + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
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-
?
additional information
?
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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)-phenylacetaldehyde oxime
(Z)-phenylacetaldehyde oxime
show the reaction diagram
A0A068Q609
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-
-
?
(E)-phenylacetaldehyde oxime + [reduced NADPH-hemoprotein reductase] + O2
(R)-mandelonitrile + [oxidized NADPH-hemoprotein reductase] + 2 H2O
show the reaction diagram
A0A068Q609
-
overall reaction
-
?
(Z)-phenylacetaldehyde oxime
phenylacetonitrile + H2O
show the reaction diagram
A0A068Q609
-
-
-
?
phenylacetonitrile + [reduced NADPH-hemoprotein reductase] + O2
(R)-mandelonitrile + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
A0A068Q609
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-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0039
(E)-phenylacetaldehyde oxime
pH 7.6, 30°C
0.007
4-hydroxyphenylacetaldoxime
pH 7.6, 30°C
0.195
4-Hydroxyphenylacetonitrile
pH 7.6, 30°C
0.0082
indole-3-acetaldoxime
pH 7.6, 30°C
0.751
indole-3-acetonitrile
pH 7.6, 30°C
0.0185
phenylacetonitrile
pH 7.6, 30°C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.77
(E)-phenylacetaldehyde oxime
pH 7.6, 30°C
0.62
4-hydroxyphenylacetaldoxime
pH 7.6, 30°C
0.57
4-Hydroxyphenylacetonitrile
pH 7.6, 30°C
0.028
indole-3-acetaldoxime
pH 7.6, 30°C
0.1
indole-3-acetonitrile
pH 7.6, 30°C
0.4
phenylacetonitrile
pH 7.6, 30°C
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE