Entry
Name
(methylsulfanyl)alkanaldoxime N-monooxygenase;
CYP83A1 (gene name);
(methylthio)alkanaldoxime N-monooxygenase;
(E)-omega-(methylthio)alkananaldoxime,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (N-hydroxylating)
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)-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
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