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
PPER: 18776644
PMUM: 103337951
PAVI: 110745870
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

DBGET integrated database retrieval system