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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.

The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

Synonyms
cyp79a2, cyp79d16, 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
show the reaction diagram
overall reaction
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L-phenylalanine + [reduced NADPH-hemoprotein reductase] + O2 = N-hydroxy-L-phenylalanine + [oxidized NADPH-hemoprotein reductase] + 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 + [reduced NADPH-hemoprotein reductase] + O2 = N,N-dihydroxy-L-phenylalanine + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(1b)
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