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EC 1.14.14.40 Details
show Brenda entryEC number
1.14.14.40
Accepted name
phenylalanine N-monooxygenase
Reaction
L-phenylalanine + 2 [reduced NADPH—hemoprotein reductase] + 2 O2 = (E)-phenylacetaldoxime + 2 [oxidized NADPH—hemoprotein reductase] + CO2 + 3 H2O (overall reaction);;(1a) L-phenylalanine + [reduced NADPH—hemoprotein reductase] + O2 = N-hydroxy-L-phenylalanine + [oxidized NADPH—hemoprotein reductase] + H2O;;(1b) N-hydroxy-L-phenylalanine + [reduced NADPH—hemoprotein reductase] + O2 = N,N-dihydroxy-L-phenylalanine + [oxidized NADPH—hemoprotein reductase] + H2O;;(1c) N,N-dihydroxy-L-phenylalanine = (E)-phenylacetaldoxime + CO2 + H2O
Other name(s)
phenylalanine N-hydroxylase,
CYP79A2 (gene name),
CYP79D16 (gene name)
Systematic name
L-phenylalanine,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (N-hydroxylating)
Comment
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.
History
created 2011 as EC 1.14.13.124, transferred 2017 to EC 1.14.14.40
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1 Oxidoreductases
1.1 Acting on the CH-OH group of donors
1.14.14.2 created 1972, deleted 1976 1.14.14.4 created 2000, deleted 2002
