Entry Name 4-hydroxyphenylacetaldehyde oxime monooxygenase;
Class Oxidoreductases;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 ec01110 Biosynthesis of secondary metabolites
Orthology K13029 4-hydroxyphenylacetaldehyde oxime monooxygenase
Genes OGL : 127757956 127766310 127767304
ATS : 109733661 109735602 109737065 109737957 109747539 109747544 109748981 109750951 109751569 109769118 109769136 109784191 109784631 109787604
TDC : 119273690 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
TAES : 123038753 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
TUA : 125506544 125507185 125507186 125519012 125520908 125521830 125525404 125530820 125534714 125534716 125540626 125546339 125546342 125553160 125554388 125554970 125556349
LPER : 127340064 127344001 127344576
LRD : 124673145 124682163 124691135 124693634
SBI : 8060872 8060873 8062630 8079645 8080170
MFLO : 136509411 136517147 136517747 136517755 136527640 136531364 136537575 136537641
SITA : 101753396 101754601 101756641 101762885 101769877 101772694 101783611 101784688 101785891
SVS : 117837674 117837675 117839019 117839020 117839767 117840283 117844932 117845599 117845682 117850994 117851590
PVIR : 120645955 120649096 120654079 120669347 120685182 120703721
PHAI : 112875832 112875833 112877365 112900397
PAUA : 133913782 133915007 133915008
» show all Taxonomy Reference 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 Authors Shimada M, Conn EE.
Title The enzymatic conversion of p-hydroxyphenylacetaldoxime to p-hydroxymandelonitrile.
Journal Reference 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 Reference 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 Reference 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 Other DBs
