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
ATHAT5G05260(CYP79A2) AT5G35917(CYP79A3P)
ALY9309270
CRB17881204
CSAT104768722 109128315
EUSEUTSA_v10015246mg
BRP103846879 103850577
BNA106419211 106422714 106444566
BOE106316016 106325663
RSZ108815254 108817168
THJ104816511
CIT102609684 102612895 102614859 102624911 102625186 102626076 112498657
CICCICLE_v10004690mg CICLE_v10013842mg CICLE_v10025237mg CICLE_v10025240mg CICLE_v10031099mg CICLE_v10031307mg CICLE_v10031309mg CICLE_v10031311mg CICLE_v10033385mg
TCC108663677 18507087 18587457 18587459 18587467
GRA105778382
GHI107902522 107916288
GAB108451448 108488256
DZI111296525 111296568 111296751 111309678 111309679
FVE101302920
RCN112181561
PPER18769536 18770648
PMUM103339830
PAVI110756169 110765955 110766314
PDUL117634481 117635145
PXB103945226 103945228
ZJU107410645 107410670
MNT21387266 21387267 21388226
CSV101215668
CMO103492071
BHJ120069839 120071707
JRE108985109 108985183
QSU112000129
QLO115976056 115994657 115994668
VVI100241541 100249616 100253513 100255415 100260154 100263812 100265709
VRI117916857 117916953 117927469 117927736 117927737 117927992 117928002 117928012
ITR116030760
NNU104594490
MING122059902 122075084 122081088 122081317
TSS122644564 122646897
PSOM113283672 113329421 113338899 113353323 113357858 113361912
NCOL116263110
 » 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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