Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
BRITE hierarchy

L-phenylalanine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (N-hydroxylating)

L-phenylalanine + 2 [reduced NADPH---hemoprotein reductase] + 2 O2 = (E)-phenylacetaldoxime + 2 [oxidized NADPH---hemoprotein reductase] + CO2 + 3 H2O (overall reaction) [RN:R09578];
(1a) L-phenylalanine + [reduced NADPH---hemoprotein reductase] + O2 = N-hydroxy-L-phenylalanine + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R09579];
(1b) N-hydroxy-L-phenylalanine + [reduced NADPH---hemoprotein reductase] + O2 = N,N-dihydroxy-L-phenylalanine + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R09580];
(1c) N,N-dihydroxy-L-phenylalanine = (E)-phenylacetaldoxime + CO2 + H2O [RN:R09581]

R09578 R09579 R09580 R09581;
(other) R08652
Reaction

L-phenylalanine [CPD:C00079];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007];
N-hydroxy-L-phenylalanine [CPD:C19712];
N,N-dihydroxy-L-phenylalanine [CPD:C19715]

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.

EC 1.14.14.40 created 2011 as EC 1.14.13.124, transferred 2017 to EC 1.14.14.40

1  [PMID:10799553]

2  [PMID:25015725]