KEGG   ENZYME: 1.14.14.40Help
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
BRITE hierarchy
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)
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
Cyanoamino acid metabolism
Glucosinolate biosynthesis
Biosynthesis of secondary metabolites
Orthology
K12153  
phenylalanine N-monooxygenase
Genes
ATH: 
AT5G05260(CYP79A2)
ALY: 
CRB: 
EUS: 
BRP: 
103846879 103850577(CYP79A2-1)
BNA: 
THJ: 
CIT: 
CIC: 
TCC: 
GRA: 
105764693 105770855 105778382 105803050
GHI: 
107889976 107892099 107902522 107906304 107915648 107954985 107956795 107956797 107958525
EGR: 
104420177
GMX: 
100779934 100785254 100786887 100787378 100809902
PVU: 
PHAVU_006G002300g PHAVU_006G0788000 PHAVU_006G078900g PHAVU_006G079100g PHAVU_006G0792000 PHAVU_010G076800g
VRA: 
106774698 106774787 106774788 106774789 106774790 106774791 106775278 106778952 106779949 106779950 106779957
VAR: 
108319396 108341438 108341520 108341521 108341522 108342345 108342438
CCAJ: 
109792068 109813922 109815538 109816881 109816892 109816894 109816895
MTR: 
MTR_3g465300 MTR_3g467200 MTR_3g467220 MTR_3g467290 MTR_8g073950 MTR_8g076372 MTR_8g076390
CAM: 
101513975 101514837 101515486
ADU: 
107463188 107473984 107474843 107474849 107475187 107478497 107486438
AIP: 
107612299 107634313 107637425 107638189 107640405 107644259 107644267
LJA: 
Lj0g3v0058079.1(Lj0g3v0058079.1) Lj0g3v0066989.1(Lj0g3v0066989.1) Lj0g3v0066989.2(Lj0g3v0066989.2) Lj0g3v0086169.1(Lj0g3v0086169.1) Lj0g3v0323829.1(Lj0g3v0323829.1) Lj0g3v0323839.1(Lj0g3v0323839.1) Lj3g3v0744710.1(Lj3g3v0744710.1) Lj3g3v0744720.1(Lj3g3v0744720.1) Lj6g3v0326370.1(Lj6g3v0326370.1)
LANG: 
109329009 109329069
FVE: 
101302920
PPER: 
18769536 18770648 18775172
PMUM: 
103330459 103339830
MDM: 
103412907 103429934 103447598 108171946
PXB: 
103945226 103945228 103958933
ZJU: 
107410640 107410645 107410648 107410651 107410670
CSV: 
101215668 101215911 101216155 101216819 101217397
CMO: 
103491937 103492071
RCU: 
107261602 8275042 8282194 8282195 8282449
JCU: 
105638772 105638782 105638807 105640577 105640586
POP: 
POPTR_0013s15310g POPTR_0013s15320g(POPTRDRAFT_571904) POPTR_1061s00200g
VVI: 
100241541 100246526 100249616 100253513 100255415 100260154 100263812 100265709 109122751
SLY: 
101244179 101253063 101257394 101257953
SPEN: 
107006880 107016389 107016571 107017521 107028238
SOT: 
102593505 102597216 102599701 102605273 102605603
INI: 
109158645 109158646 109158773 109158774 109158776 109158778 109158852 109158863 109181069 109181142 109181143 109181364 109182061
SIND: 
105156979 105157077 105157078 105157080 105160146 105166505 105177046 105177047
NNU: 
104594490
ATS: 
F775_19739 F775_25726
ZMA: 
103626061 103626086 103644042
PDA: 
103720455
EGU: 
105032989
 » 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]
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 (2014) 215-23.
  Sequence
[pmum:103330459]
Other DBs
ExplorEnz - The Enzyme Database: 
IUBMB Enzyme Nomenclature: 
ExPASy - ENZYME nomenclature database: 
BRENDA, the Enzyme Database: 
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