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Information on EC 1.14.14.45 - aromatic aldoxime N-monooxygenase

for references in articles please use BRENDA:EC1.14.14.45
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IUBMB Comments
This cytochrome P-450 (heme thiolate) enzyme is involved in the biosynthesis of glucosinolates in plants. The enzyme catalyses the N-hydroxylation of aromatic aldoximes derived from L-tryptophan, L-phenylalanine, and L-tyrosine, 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 glutathione, the enzyme is suicidal, probably due to interaction of the reactive aci-nitro compound with catalytic residues in the active site.
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The enzyme appears in viruses and cellular organisms
Synonyms
At4g31500, CYP83B1, cytochrome P450 83B1, HM347235, more
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(E)-indol-3-ylacetaldehyde oxime + [reduced NADPH-hemoprotein reductase] + glutathione + O2 = S-[(E)-N-hydroxy(indol-3-yl)acetimidoyl]-L-glutathione + [oxidized NADPH-hemoprotein reductase] + 2 H2O
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(1), overall reaction
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(E)-indol-3-ylacetaldehyde oxime + [reduced NADPH-hemoprotein reductase] + O2 = 1-(1H-indol-3-yl)-2-aci-nitroethane + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(1a)
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(E)-phenylacetaldehyde oxime + [reduced NADPH-hemoprotein reductase] + glutathione + O2 = S-[(Z)-N-hydroxy(phenyl)acetimidoyl]-L-glutathione + [oxidized NADPH-hemoprotein reductase] + 2 H2O
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(2), overall reaction
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(E)-phenylacetaldehyde oxime + [reduced NADPH-hemoprotein reductase] + O2 = 1-aci-nitro-2-phenylethane + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
(2a)
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1-(1H-indol-3-yl)-2-aci-nitroethane + glutathione = S-[(E)-N-hydroxy(indol-3-yl)acetimidoyl]-L-glutathione + H2O
show the reaction diagram
(1b), spontaneous
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1-aci-nitro-2-phenylethane + glutathione = S-[(Z)-N-hydroxy(phenyl)acetimidoyl]-L-glutathione + H2O
show the reaction diagram
(2b), spontaneous
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