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)
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
PPER18776644
PMUM103337951
PAVI110745870
PDUL117627354 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

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