KEGG   ORTHOLOGY: K13029
Entry
K13029                      KO                                     

Name
CYP71E1
Definition
4-hydroxyphenylacetaldehyde oxime monooxygenase [EC:1.14.14.37]
Pathway
ko00460  Cyanoamino acid metabolism
ko01100  Metabolic pathways
ko01110  Biosynthesis of secondary metabolites
Module
M00369  Cyanogenic glycoside biosynthesis, tyrosine => dhurrin
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09106 Metabolism of other amino acids
   00460 Cyanoamino acid metabolism
    K13029  CYP71E1; 4-hydroxyphenylacetaldehyde oxime monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K13029  CYP71E1; 4-hydroxyphenylacetaldehyde 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
    1.14.14.37  4-hydroxyphenylacetaldehyde oxime monooxygenase
     K13029  CYP71E1; 4-hydroxyphenylacetaldehyde oxime monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP71 family
   K13029  CYP71E1; 4-hydroxyphenylacetaldehyde oxime monooxygenase
Other DBs
RN: R02708 R04306 R05728 R11442
GO: 0050592
Genes
OSA: 4334792
DOSA: Os12t0512800-01(Os12g0512800)
OBR: 102707538
BDI: 100827324 100827625
ATS: 109735602(LOC109735602) 109784191(LOC109784191)
SBI: 8060872 8060873
ZMA: 100194166
SITA: 101769877 101783611 101784688 101785891
Reference
PMID:9484480
  Authors
Bak S, Kahn RA, Nielsen HL, Moller BL, Halkier BA
  Title
Cloning of three A-type cytochromes P450, CYP71E1, CYP98, and CYP99 from Sorghum bicolor (L.) Moench by a PCR approach and identification by expression in Escherichia coli of CYP71E1 as a multifunctional cytochrome P450 in the biosynthesis of the cyanogenic glucoside dhurrin.
  Journal
Plant Mol Biol 36:393-405 (1998)
DOI:10.1023/A:1005915507497
  Sequence
[sbi:8060873]

KEGG   ENZYME: 1.14.14.37
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
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: 109735602(LOC109735602) 109784191(LOC109784191)
SBI: 8060872 8060873
ZMA: 100194166
SITA: 101769877 101783611 101784688 101785891
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

KEGG   REACTION: R05728
Entry
R05728                      Reaction                               

Name
(E)-4-hydroxyphenylacetaldehyde oxime,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase
Definition
(E)-4-Hydroxyphenylacetaldehyde oxime + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> (S)-4-Hydroxymandelonitrile + [Oxidized NADPH---hemoprotein reductase] + 2 H2O
Equation
Comment
three-step reaction (R11442+R04306+R02708)
Enzyme
Pathway
rn00460  Cyanoamino acid metabolism
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00369  Cyanogenic glycoside biosynthesis, tyrosine => dhurrin
Orthology
K13029  4-hydroxyphenylacetaldehyde oxime monooxygenase [EC:1.14.14.37]
Other DBs
RHEA: 18404

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