KEGG   ORTHOLOGY: K12153
Entry
K12153                      KO                                     

Name
CYP79A2
Definition
phenylalanine N-monooxygenase [EC:1.14.14.40]
Pathway
ko00460  Cyanoamino acid metabolism
ko00966  Glucosinolate biosynthesis
ko01100  Metabolic pathways
ko01110  Biosynthesis of secondary metabolites
ko01210  2-Oxocarboxylic acid metabolism
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09106 Metabolism of other amino acids
   00460 Cyanoamino acid metabolism
    K12153  CYP79A2; phenylalanine N-monooxygenase
  09110 Biosynthesis of other secondary metabolites
   00966 Glucosinolate biosynthesis
    K12153  CYP79A2; phenylalanine N-monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K12153  CYP79A2; phenylalanine N-monooxygenase
Enzymes [BR:ko01000]
 1. Oxidoreductases
  1.14  Acting on paired donors, with incorporation or reduction of molecular oxygen
   1.14.14  With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
    1.14.14.40  phenylalanine N-monooxygenase
     K12153  CYP79A2; phenylalanine N-monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP79 family
   K12153  CYP79A2; phenylalanine N-monooxygenase
Other DBs
RN: R08652 R09578 R09579 R09580 R09581
Genes
ATH: AT5G05260(CYP79A2)
ALY: 9309270 9324309
CRB: 17881204 17888733 17894076 17894418
CSAT: 104737845 104754030 104768722 104785191 104789417 104793102 109128315
EUS: EUTSA_v10015246mg EUTSA_v10017915mg
BRP: 103846879 103850577 103854360 103857228 103865913 103867719 117132118
BNA: 106359381 106378673 106391752 106392762 106419211 106422714 106424858 106441284 106441615 106444566 106450307
BOE: 106316016 106321702 106324352 106325663 106333603 106338032 106342122
RSZ: 108807966 108807967 108808749 108810018 108815254 108817168 108831493 108831495 108838807 108838815 108839086
THJ: 104806386 104808358 104808359 104813305 104816511
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
  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]

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: 9309270 9324309
CRB: 17881204 17888733 17894076 17894418
CSAT: 104737845 104754030 104768722 104785191 104789417 104793102 109128315
EUS: EUTSA_v10015246mg EUTSA_v10017915mg
BRP: 103846879 103850577 103854360 103857228 103865913 103867719 117132118
BNA: 106359381 106378673 106391752 106392762 106419211 106422714 106424858 106441284 106441615 106444566 106450307
BOE: 106316016 106321702 106324352 106325663 106333603 106338032 106342122
RSZ: 108807966 108807967 108808749 108810018 108815254 108817168 108831493 108831495 108838807 108838815 108839086
THJ: 104806386 104808358 104808359 104813305 104816511
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

KEGG   REACTION: R09581
Entry
R09581                      Reaction                               

Definition
N,N-Dihydroxy-L-phenylalanine <=> (E)-Phenylacetaldoxime + CO2 + H2O
Equation
Comment
the last step of three-step reaction (see R09578, R09579+R09580+R09581)
Reaction class
RC01936  C19714_C19715
Enzyme
Pathway
rn00460  Cyanoamino acid metabolism
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Orthology
K12153  phenylalanine N-monooxygenase [EC:1.14.14.40]
Other DBs
RHEA: 25003

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