Entry Name (methylsulfanyl)alkanaldoxime N-monooxygenase;
Class Oxidoreductases;BRITE hierarchy
Sysname (E)-omega-(methylsulfanyl)alkananal oxime,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (N-hydroxylating)
Reaction(IUBMB) an (E)-omega-(methylsulfanyl)alkanal oxime + [reduced NADPH---hemoprotein reductase] + glutathione + O2 = an S-[(1E)-1-(hydroxyimino)-omega-(methylsulfanyl)alkyl]-L-glutathione + [oxidized NADPH---hemoprotein reductase] + 2 H2O (overall reaction) [RN:
R11650 ];
(1a) an (E)-omega-(methylsulfanyl)alkanal oxime + [reduced NADPH---hemoprotein reductase] + O2 = a 1-(methylsulfanyl)-4-aci-nitroalkane + [oxidized NADPH---hemoprotein reductase] + H2O [RN:
R11651 ];
(1b) a 1-(methylsulfanyl)-4-aci-nitroalkane + glutathione = an S-[(1E)-1-(hydroxyimino)-omega-(methylsulfanyl)alkyl]-L-glutathione + H2O [RN:
R11652 ]
Reaction(KEGG) Substrate (E)-omega-(methylsulfanyl)alkanal oxime [CPD:
C21535 ];
[reduced NADPH---hemoprotein reductase] [CPD:
C03024 ];
glutathione [CPD:
C00051 ];
O2 [CPD:
C00007 ];
1-(methylsulfanyl)-4-aci-nitroalkane [CPD:
C21538 ]
Product S-[(1E)-1-(hydroxyimino)-omega-(methylsulfanyl)alkyl]-L-glutathione [CPD:
C21539 ];
[oxidized NADPH---hemoprotein reductase] [CPD:
C03161 ];
H2O [CPD:
C00001 ];
1-(methylsulfanyl)-4-aci-nitroalkane [CPD:
C21538 ]
Comment This cytochrome P-450 (heme thiolate) enzyme is involved in the biosynthesis of glucosinolates in plants. The enzyme catalyses an N-hydroxylation of the E isomer of omega-(methylsulfanyl)alkanal oximes, forming an aci-nitro intermediate that reacts non-enzymically with glutathione to produce an N-alkyl-thiohydroximate adduct, the committed precursor of glucosinolates. In the absence of a thiol compound, the enzyme is suicidal, probably due to interaction of the reactive aci-nitro intermediate with active site residues.
History EC 1.14.14.43 created 2017
Pathway Orthology K12156 (methylthio)alkanaldoxime N-monooxygenase
Genes CSAT : 104719080 104732331 104772976 104773989
BNA : 106391682 106426995 106430121 106447562
THJ : 104806927 104813171 104822821
Taxonomy Reference Authors Bak S, Tax FE, Feldmann KA, Galbraith DW, Feyereisen R
Title CYP83B1, a cytochrome P450 at the metabolic branch point in auxin and indole glucosinolate biosynthesis in Arabidopsis.
Journal Reference Authors Naur P, Petersen BL, Mikkelsen MD, Bak S, Rasmussen H, Olsen CE, Halkier BA
Title CYP83A1 and CYP83B1, two nonredundant cytochrome P450 enzymes metabolizing oximes in the biosynthesis of glucosinolates in Arabidopsis.
Journal Sequence 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
