KEGG   ENZYME: 1.14.14.40
Entry
EC 1.14.14.40               Enzyme                                 

Name
phenylalanine N-monooxygenase;
phenylalanine N-hydroxylase;
CYP79A2 (gene name);
CYP79D16 (gene name)
Class
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
Sysname
L-phenylalanine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (N-hydroxylating)
Reaction(IUBMB)
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]
Reaction(KEGG)
R09578 R09579 R09580 R09581;
(other) R08652
Substrate
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]
Product
(E)-phenylacetaldoxime [CPD:C19714];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
CO2 [CPD:C00011];
H2O [CPD:C00001];
N-hydroxy-L-phenylalanine [CPD:C19712];
N,N-dihydroxy-L-phenylalanine [CPD:C19715]
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
EC 1.14.14.40 created 2011 as EC 1.14.13.124, transferred 2017 to EC 1.14.14.40
Pathway
ec00460  Cyanoamino acid metabolism
ec00966  Glucosinolate biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K12153  phenylalanine N-monooxygenase
Genes
ATH: AT5G05260(CYP79A2) AT5G35917(CYP79A3P)
ALY: 9309270
CRB: 17881204
CSAT: 104768722 109128315
EUS: EUTSA_v10015246mg
BRP: 103846879 103850577
BNA: 106419211 106422714 106444566
BOE: 106316016 106325663
RSZ: 108815254 108817168
THJ: 104816511
GRA: 105778382
FVE: 101302920
RCN: 112181561
PMUM: 103339830
CSV: 101215668
CMO: 103492071
QSU: 112000129
ITR: 116030760
NNU: 104594490
NCOL: 116263110
 » show all
Reference
1  [PMID:10799553]
  Authors
Wittstock U, Halkier BA
  Title
Cytochrome P450 CYP79A2 from Arabidopsis thaliana L. Catalyzes the conversion of L-phenylalanine to phenylacetaldoxime in the biosynthesis of benzylglucosinolate.
  Journal
J Biol Chem 275:14659-66 (2000)
DOI:10.1074/jbc.275.19.14659
  Sequence
[ath:AT5G05260]
Reference
2  [PMID:25015725]
  Authors
Yamaguchi T, Yamamoto K, Asano Y
  Title
Identification and characterization of CYP79D16 and CYP71AN24 catalyzing the first and second steps in L-phenylalanine-derived cyanogenic glycoside biosynthesis in the Japanese apricot, Prunus mume Sieb. et Zucc.
  Journal
Plant Mol Biol 86:215-23 (2014)
DOI:10.1007/s11103-014-0225-6
  Sequence
[pmum:103330459]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.40
IUBMB Enzyme Nomenclature: 1.14.14.40
ExPASy - ENZYME nomenclature database: 1.14.14.40
BRENDA, the Enzyme Database: 1.14.14.40
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