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
TWL119986676 119989269
OSA4334792 4352333
DOSAOs12t0512800-01(Os12g0512800)
OBR102706930 102707538
BDI100827324 100827625
ATS109733661 109735602 109737065 109737957 109747539 109747544 109748981 109750951 109751569 109769118 109769136 109784191 109784631 109787604
TDC119273690 119273691 119278445 119282693 119282694 119283868 119287414 119287832 119288133 119288225 119289407 119289633 119289634 119297597 119298367 119298587 119299744 119306758 119306779 119306780 119309824 119311021 119313052 119321498 119321842 119327509 119330245 119331956 119332114 119342010 119345327 119348333 119352727 119357388
TAES123038753 123059668 123059669 123059674 123067011 123067012 123067013 123072304 123072836 123075944 123080996 123082651 123082653 123082972 123082976 123083482 123084101 123088332 123089797 123100767 123107354 123108289 123108572 123116504 123116505 123117746 123117747 123117905 123117907 123122081 123125104 123126173 123126174 123133090 123133091 123146871 123150242 123150768 123154237 123154461 123154818 123156805 123159224 123159304 123166640 123169325 123170071 123170477 123170554 123172579 123175968 123176249 123176531 123184245 123186759 123191301
TUA125506544 125507185 125507186 125519012 125520908 125521830 125525404 125530820 125534714 125534716 125540626 125546339 125546342 125553160 125554388 125554970 125556349
SBI8060872 8060873 8062630 8079645 8080170
ZMA100194166
SITA101753396 101754601 101756641 101762885 101769877 101772694 101783611 101784688 101785891
SVS117837674 117837675 117839019 117839020 117839767 117840283 117844932 117845599 117845682 117850994 117851590
PVIR120645955 120649096 120654079 120669347 120685182 120703721
PHAI112875832 112875833 112877365 112900397
 » show all
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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