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)
ALY: 9324309
CRB: 17888733 17894418
CSAT: 104737845 104754030 104785191 104793102 109128315
BRP: 103846879 103854360 103857228 103865913 103867719
BNA: 106359381 106391752 106392762 106419211 106424858 106441284 106441615 106444566 106450307
BOE: 106316016 106321702 106333603 106338032 106342122
RSZ: 108807966 108807967 108808749 108817168 108831493 108831495 108838807 108838815 108839086
THJ: 104808358 104808359 104813305 104816511
CIT: 102609684 102612895 102613196 102614859 102618319 102624911 102625186 102626076 112498657
LJA: Lj0g3v0058079.1(Lj0g3v0058079.1) Lj0g3v0066989.1(Lj0g3v0066989.1) Lj0g3v0137329.1(Lj0g3v0137329.1) Lj3g3v0744710.1(Lj3g3v0744710.1) Lj3g3v0744720.1(Lj3g3v0744720.1) Lj6g3v0326370.1(Lj6g3v0326370.1)
FVE: 101302920
CMAX: 111485430
NNU: 104594490
OSA: 4335062
DOSA: Os04t0171600-01(Os04g0171600) Os04t0171800-01(Os04g0171800)
OBR: 102721537
ATS: 109734623(LOC109734623) 109739830(LOC109739830) 109756299(LOC109756299) 109759062(LOC109759062) 109759066(LOC109759066) 109768717(LOC109768717) 109773762(LOC109773762) 109773764(LOC109773764) 109773765(LOC109773765) 109787578(LOC109787578)
SITA: 101761087
PDA: 103720455
 » 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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