KEGG   ENZYME: 1.14.14.37Help
Entry
EC 1.14.14.37               Enzyme                                 

Name
4-hydroxyphenylacetaldehyde oxime monooxygenase;
4-hydroxybenzeneacetaldehyde oxime monooxygenase;
cytochrome P450II-dependent monooxygenase;
NADPH-cytochrome P450 reductase (CYP71E1);
CYP71E1;
4-hydroxyphenylacetaldehyde oxime,NADPH:oxygen oxidoreductase
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
BRITE hierarchy
Sysname
(E)-4-hydroxyphenylacetaldehyde oxime,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase
Reaction(IUBMB)
(E)-4-hydroxyphenylacetaldehyde oxime + [reduced NADPH---hemoprotein reductase] + O2 = (S)-4-hydroxymandelonitrile + [oxidized NADPH---hemoprotein reductase] + 2 H2O (overall reaction) [RN:R05728];
(1a) (E)-4-hydroxyphenylacetaldehyde oxime = (Z)-4-hydroxyphenylacetaldehyde oxime [RN:R11442];
(1b) (Z)-4-hydroxyphenylacetaldehyde oxime = 4-hydroxyphenylacetonitrile + H2O [RN:R04306];
(1c) 4-hydroxyphenylacetonitrile + [reduced NADPH---hemoprotein reductase] + O2 = (S)-4-hydroxymandelonitrile + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R02708]
Reaction(KEGG)
Substrate
(E)-4-hydroxyphenylacetaldehyde oxime [CPD:C04350];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007];
(Z)-4-hydroxyphenylacetaldehyde oxime [CPD:C04353];
4-hydroxyphenylacetonitrile [CPD:C03766]
Product
(S)-4-hydroxymandelonitrile [CPD:C03742];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001];
(Z)-4-hydroxyphenylacetaldehyde oxime [CPD:C04353];
4-hydroxyphenylacetonitrile [CPD:C03766]
Comment
This cytochrome P-450 (heme thiolate) enzyme is involved in the biosynthesis of the cyanogenic glucoside dhurrin in sorghum. It catalyses three different activities - isomerization of the (E) isomer to the (Z) isomer, dehydration, and C-hydroxylation.
History
EC 1.14.14.37 created 2000 as EC 1.14.13.68, modified 2005, transferred 2016 to EC 1.14.14.37
Pathway
ec00460  Cyanoamino acid metabolism
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K13029  4-hydroxyphenylacetaldehyde oxime monooxygenase
Genes
OSA: 4334792
DOSA: Os12t0512800-01(Os12g0512800)
OBR: 102707538
BDI: 100827324 100827625
ATS: 109784191(LOC109784191)
SBI: 8060872 8060873
ZMA: 100194166
SITA: 101769877 101783611 101784688 101785891
Taxonomy
Reference
1  [PMID:237909]
  Authors
MacFarlane IJ, Lees EM, Conn EE.
  Title
The in vitro biosynthesis of dhurrin, the cyanogenic glycoside of Sorghum bicolor.
  Journal
J Biol Chem 250:4708-13 (1975)
Reference
2  [PMID:193443]
  Authors
Shimada M, Conn EE.
  Title
The enzymatic conversion of p-hydroxyphenylacetaldoxime to p-hydroxymandelonitrile.
  Journal
Arch Biochem Biophys 180:199-207 (1977)
DOI:10.1016/0003-9861(77)90026-1
Reference
3  [PMID:12114576]
  Authors
Busk PK, Moller BL.
  Title
Dhurrin synthesis in sorghum is regulated at the transcriptional level and induced by nitrogen fertilization in older plants.
  Journal
Plant Physiol 129:1222-31 (2002)
DOI:10.1104/pp.000687
Reference
4  [PMID:15665094]
  Authors
Kristensen C, Morant M, Olsen CE, Ekstrom CT, Galbraith DW, Moller BL, Bak S.
  Title
Metabolic engineering of dhurrin in transgenic Arabidopsis plants with marginal inadvertent effects on the metabolome and transcriptome.
  Journal
Proc Natl Acad Sci U S A 102:1779-84 (2005)
DOI:10.1073/pnas.0409233102
Reference
5  [PMID:26361733]
  Authors
Clausen M, Kannangara RM, Olsen CE, Blomstedt CK, Gleadow RM, Jorgensen K, Bak S, Motawie MS, Moller BL
  Title
The bifurcation of the cyanogenic glucoside and glucosinolate biosynthetic pathways.
  Journal
Plant J 84:558-73 (2015)
DOI:10.1111/tpj.13023
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.37
IUBMB Enzyme Nomenclature: 1.14.14.37
ExPASy - ENZYME nomenclature database: 1.14.14.37
BRENDA, the Enzyme Database: 1.14.14.37

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