KEGG   ENZYME: 1.14.13.124Help
Entry
EC 1.14.13.124              Enzyme                                 

Name
phenylalanine N-monooxygenase;
phenylalanine N-hydroxylase;
CYP79A2
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With NADH or NADPH as one donor, and incorporation of one atom of oxygen into the other donor
BRITE hierarchy
Sysname
L-phenylalanine,NADPH:oxygen oxidoreductase (N-hydroxylating)
Reaction(IUBMB)
L-phenylalanine + 2 O2 + 2 NADPH + 2 H+ = (E)-phenylacetaldoxime + 2 NADP+ + CO2 + 3 H2O (overall reaction) [RN:R09578];
(1a) L-phenylalanine + O2 + NADPH + H+ = N-hydroxy-L-phenylalanine + NADP+ + H2O [RN:R09579];
(1b) N-hydroxy-L-phenylalanine + O2 + NADPH + H+ = N,N-dihydroxy-L-phenylalanine + NADP+ + H2O [RN:R09580];
(1c) N,N-dihydroxy-L-phenylalanine = (E)-phenylacetaldoxime + CO2 + H2O [RN:R09581]
Reaction(KEGG)
Substrate
L-phenylalanine [CPD:C00079];
O2 [CPD:C00007];
NADPH [CPD:C00005];
H+ [CPD:C00080];
N-hydroxy-L-phenylalanine [CPD:C19712];
N,N-dihydroxy-L-phenylalanine [CPD:C19715]
Product
(E)-phenylacetaldoxime [CPD:C19714];
NADP+ [CPD:C00006];
CO2 [CPD:C00011];
H2O [CPD:C00001];
N-hydroxy-L-phenylalanine [CPD:C19712];
N,N-dihydroxy-L-phenylalanine [CPD:C19715]
Comment
A heme-thiolate protein (P-450). This enzyme catalyses two successive N-hydroxylations of L-phenylalanine, the first committed steps in the biosynthesis of benzylglucosinolate. The product of the two hydroxylations, N,N-dihydroxy-L-phenylalanine, is extremely labile and dehydrates spontaneously.The dehydrated product is then subject to a decarboxylation that produces the oxime. It is still not known whether the decarboxylation is spontaneous or catalysed by the enzyme. The product, (E)-phenylacetaldoxime, undergoes a spontaneous isomerization to the (Z) form.
History
EC 1.14.13.124 created 2011
Pathway
Cyanoamino acid metabolism
Glucosinolate biosynthesis
Biosynthesis of secondary metabolites
Orthology
K12153  
phenylalanine N-monooxygenase
Genes
ATH: 
AT5G05260(CYP79A2)
ALY: 
CRB: 
EUS: 
BRP: 
CIT: 
CIC: 
TCC: 
GMX: 
PVU: 
MTR: 
CAM: 
FVE: 
PPER: 
PMUM: 
MDM: 
PXB: 
CSV: 
CMO: 
RCU: 
POP: 
VVI: 
SLY: 
SOT: 
SBI: 
SORBI_01g016150(SORBIDRAFT_01g016150) SORBI_01g016480(SORBIDRAFT_01g016480)
ZMA: 
PDA: 
 » show all
Taxonomy
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 (2000) 14659-66.
  Sequence
[ath:AT5G05260]
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 

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