KEGG   ORTHOLOGY: K00495
Entry
K00495            Tight     KO                                     
Symbol
CYP71AN24
Name
phenylacetaldehyde oxime monooxygenase [EC:1.14.14.44]
Pathway
map00460  Cyanoamino acid metabolism
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Reaction
R07638  (Z)-phenylacetaldehyde-oxime hydro-lyase
R10041  
R11733  phenylacetonitrile,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase [(R)-mandelonitrile-forming]
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09106 Metabolism of other amino acids
   00460 Cyanoamino acid metabolism
    K00495  CYP71AN24; phenylacetaldehyde oxime monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K00495  CYP71AN24; phenylacetaldehyde oxime 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
    1.14.14.44  phenylacetaldehyde oxime monooxygenase
     K00495  CYP71AN24; phenylacetaldehyde oxime monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP71 family
   K00495  CYP71AN24; phenylacetaldehyde oxime monooxygenase
Genes
PPER: 18776644
PMUM: 103337951
PAVI: 110745870
PDUL: 117627354 117628317 117628484
Reference
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:103337951]
LinkDB

KEGG   ENZYME: 1.14.14.44
Entry
EC 1.14.14.44               Enzyme                                 
Name
phenylacetaldehyde oxime monooxygenase;
CYP71AN24 (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
(E)-phenylacetaldehyde oxime,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase
Reaction(IUBMB)
(E)-phenylacetaldehyde oxime + [reduced NADPH---hemoprotein reductase] + O2 = (R)-mandelonitrile + [oxidized NADPH---hemoprotein reductase] + 2 H2O (overall reaction) [RN:R11732];
(1a) (E)-phenylacetaldehyde oxime = (Z)-phenylacetaldehyde oxime [RN:R10041];
(1b) (Z)-phenylacetaldehyde oxime = phenylacetonitrile + H2O [RN:R07638];
(1c) phenylacetonitrile + [reduced NADPH---hemoprotein reductase] + O2 = (R)-mandelonitrile + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R11733]
Reaction(KEGG)
R07638 R10041 R11732 R11733
Substrate
(E)-phenylacetaldehyde oxime [CPD:C19714];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007];
(Z)-phenylacetaldehyde oxime [CPD:C16075];
phenylacetonitrile [CPD:C16074]
Product
(R)-mandelonitrile [CPD:C00561];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001];
(Z)-phenylacetaldehyde oxime [CPD:C16075];
phenylacetonitrile [CPD:C16074]
Comment
This cytochrome P-450 (heme-thiolate) enzyme is involved in the biosynthesis of the cyanogenic glucosides (R)-prunasin and (R)-amygdalin. It catalyses three different activities - isomerization of the (E) isomer to the (Z) isomer, dehydration, and C-hydroxylation.
History
EC 1.14.14.44 created 2017
Pathway
ec00460  Cyanoamino acid metabolism
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K00495  phenylacetaldehyde oxime monooxygenase
Genes
PPER: 18776644
PMUM: 103337951
PAVI: 110745870
PDUL: 117627354 117628317 117628484
Reference
1  [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:103337951]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.44
IUBMB Enzyme Nomenclature: 1.14.14.44
ExPASy - ENZYME nomenclature database: 1.14.14.44
BRENDA, the Enzyme Database: 1.14.14.44
LinkDB

KEGG   REACTION: R11733
Entry
R11733                      Reaction                               
Name
phenylacetonitrile,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase [(R)-mandelonitrile-forming]
Definition
Phenylacetonitrile + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> Mandelonitrile + [Oxidized NADPH---hemoprotein reductase] + H2O
Equation
C16074 + C03024 + C00007 <=> C00561 + C03161 + C00001
Comment
the last step of three-step reaction (see R11732, R10041+R07638+R11733)
Reaction class
RC02540  C00561_C16074
Enzyme
1.14.14.44      1.14.14.77
Pathway
rn00460  Cyanoamino acid metabolism
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Brite
Enzymatic reactions [BR:br08201]
 1. Oxidoreductase reactions
  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
    1.14.14.44
     R11733  Phenylacetonitrile + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> Mandelonitrile + [Oxidized NADPH---hemoprotein reductase] + H2O
    1.14.14.77
     R11733  Phenylacetonitrile + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> Mandelonitrile + [Oxidized NADPH---hemoprotein reductase] + H2O
Orthology
K00495  phenylacetaldehyde oxime monooxygenase [EC:1.14.14.44]
Other DBs
RHEA: 52167
LinkDB

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