Information on EC 1.14.13.124 - phenylalanine N-monooxygenase

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The expected taxonomic range for this enzyme is: Arabidopsis thaliana

EC NUMBER
COMMENTARY hide
1.14.13.124
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RECOMMENDED NAME
GeneOntology No.
phenylalanine N-monooxygenase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
L-phenylalanine + 2 O2 + 2 NADPH + 2 H+ = (E)-phenylacetaldoxime + 2 NADP+ + CO2 + 3 H2O
show the reaction diagram
overall reaction
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L-phenylalanine + O2 + NADPH + H+ = N-hydroxy-L-phenylalanine + NADP+ + H2O
show the reaction diagram
(1a)
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N,N-dihydroxy-L-phenylalanine = (E)-phenylacetaldoxime + CO2 + H2O
show the reaction diagram
(1c)
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N-hydroxy-L-phenylalanine + O2 + NADPH + H+ = N,N-dihydroxy-L-phenylalanine + NADP+ + H2O
show the reaction diagram
(1b)
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
phenylethanol biosynthesis
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Cyanoamino acid metabolism
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Glucosinolate biosynthesis
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
L-phenylalanine,NADPH:oxygen oxidoreductase (N-hydroxylating)
A heme-thiolate protein (P-450). This enzyme catalyses two successive N-hydroxylations of L-phenylalanine, the first committed steps in the biosynthesis of benzylglucosinolate. The product of the two hydroxylations, N,N-dihydroxy-L-phenylalanine, is extremely labile and dehydrates spontaneously.The dehydrated product is then subject to a decarboxylation that produces the oxime. It is still not known whether the decarboxylation is spontaneous or catalysed by the enzyme. The product, (E)-phenylacetaldoxime, undergoes a spontaneous isomerization to the (Z) form.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
CYP79A2 is involved in the biosynthesis of benzylglucosinolate
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
L-phenylalanine + O2 + NADPH + H+
(E)-phenylacetaldoxime + NADP+ + CO2 + H2O
show the reaction diagram
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additional information
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
reduced glutathione
addition of reduced glutathione to a final concentration of 3 mM stimulates aldoxime production
Tween 80
addition of Tween 80 to a final concentration of 0.083% (v/v) results in a 1.5fold increase in aldoxime production
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 7.9
compared with the activity at pH 7.5, the activity of chimeric CYP79A2 is 25% at pH 6.0, 50% at pH 6.5, 80% at pH 7.0, and 70% at pH 7.9
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli JM109 cells