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Information on EC 1.14.14.40 - phenylalanine N-monooxygenase

for references in articles please use BRENDA:EC1.14.14.40
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IUBMB Comments
This cytochrome P-450 (heme-thiolate) enzyme, found in plants, catalyses two successive N-hydroxylations of L-phenylalanine, a committed step in the biosynthesis of benzylglucosinolate and the cyanogenic glucosides (R)-prunasin and (R)-amygdalin. The product of the two hydroxylations, N,N-dihydroxy-L-phenylalanine, is labile and undergoes dehydration followed by decarboxylation, producing an oxime. It is still not known whether the decarboxylation is spontaneous or catalysed by the enzyme.
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The enzyme appears in viruses and cellular organisms
Synonyms
CYP79A1, CYP79A2, CYP79D16, cytochrome P450 79D16, more
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
L-phenylalanine + 2 [reduced NADPH-hemoprotein reductase] + 2 O2 = (E)-phenylacetaldoxime + 2 [oxidized NADPH-hemoprotein reductase] + CO2 + 3 H2O
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overall reaction
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L-phenylalanine + [reduced NADPH-hemoprotein reductase] + O2 = N-hydroxy-L-phenylalanine + [oxidized NADPH-hemoprotein reductase] + H2O
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(1a)
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N,N-dihydroxy-L-phenylalanine = (E)-phenylacetaldoxime + CO2 + H2O
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(1c)
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N-hydroxy-L-phenylalanine + [reduced NADPH-hemoprotein reductase] + O2 = N,N-dihydroxy-L-phenylalanine + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(1b)
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