1.14.14.45: aromatic aldoxime N-monooxygenase
This is an abbreviated version!
For detailed information about aromatic aldoxime N-monooxygenase, go to the full flat file.
Reaction
Synonyms
At4g31500, CYP83B1, cytochrome P450 83B1, HM347235
ECTree
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Substrates Products
Substrates Products on EC 1.14.14.45 - aromatic aldoxime N-monooxygenase
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REACTION DIAGRAM
(E)-4-hydroxyphenylacetaldoxime + O2 + [reduced NADPH-hemoprotein reductase]
1-aci-nitro-2-(4-hydroxyphenyl)-ethane + H2O + [oxidized NADPH-hemoprotein reductase]
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(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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overall reaction
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(E)-p-hydroxyphenylacetaldehyde oxime + [reduced NADPH-hemoprotein reductase] + glutathione + O2
S-[(Z)-N-hydroxy(p-hydroxyphenyl)acetimidoyl]-L-glutathione + [oxidized NADPH-hemoprotein reductase] + 2 H2O
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overall reaction
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(E)-p-hydroxyphenylacetaldoxime + NADPH + H+ + 2-mercaptoethanol
(Z)-2-hydroxyethyl N,4-dihydroxybenzene-1-carboximidothioate + NADP+ + H2O
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CYP83B1 shows absolute specificity towards (E)-p-hydroxyphenylacetaldoxime as a substrate, and the (Z)-S-alkyl-thiohydroximate formed maintains the structural configuration of the oxime function as in the (E)-p-hydroxyphenylacetaldoxime substrate
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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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overall reaction
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(E)-phenylacetaldoxime + O2 + [reduced NADPH-hemoprotein reductase]
1-aci-nitro-2-phenylethane + H2O + [oxidized NADPH-hemoprotein reductase]
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1-aci-nitro-2-(4-hydroxyphenyl)-ethane + 2-mercaptoethanol
(Z)-2-hydroxyethyl N-hydroxy-2-(4-hydroxyphenyl)ethanimidothioate + H2O
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an (E)-omega-(methylthio)alkanal oxime + O2 + glutathione + [reduced NADPH-hemoprotein reductase]
an (E)-1-(glutathione-S-yl)-omega-(methylthio)alkylhydroximate + 2 H2O + [oxidized NADPH-hemoprotein reductase]
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indole-3-acetaldoxime + O2 + glutathione + [reduced NADPH-hemoprotein reductase]
1-aci-nitro-2-indolyl-ethane + H2O + [oxidized NADPH-hemoprotein reductase]
indole-3-acetaldoxime + [reduced NADPH-hemoprotein reductase] + O2
1-aci-nitro-2-indolyl-ethane + [oxidized NADPH-hemoprotein reductase] + 2 H2O
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the aci-nitro compound formed reacts non-enzymatically with thiol compounds to produce an N-alkyl-thiohydroximate adduct, the committed precursor of glucosinolates
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p-hydroxyphenylacetaldoxime + [reduced NADPH-hemoprotein reductase] + cysteine + O2
S-(benzohydroximoyl)-L-cysteine + [oxidized NADPH-hemoprotein reductase] + 2 H2O
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overall reaction
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p-hydroxyphenylacetaldoxime + [reduced NADPH-hemoprotein reductase] + N-acetylcysteine + O2
S-(benzohydroximoyl)-N-acetyl-L-cysteine + [oxidized NADPH-hemoprotein reductase] + 2 H2O
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overall reaction
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1-aci-nitro-2-indolyl-ethane + H2O + [oxidized NADPH-hemoprotein reductase]
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indole-3-acetaldoxime + O2 + glutathione + [reduced NADPH-hemoprotein reductase]
1-aci-nitro-2-indolyl-ethane + H2O + [oxidized NADPH-hemoprotein reductase]
indole-3-acetaldoxime is the physiological substrate for CYP83B1
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CYP83B1 catalyzes the conversion of the (E)-p-hydroxyphenylacetaldoxime into an S-alkyl-thiohydroximate with retention of the configuration of the E-oxime intermediate in the final glucosinolate core structure. CYP83B1 from Arabidopsis thaliana cannot convert the (E)-p-hydroxyphenylacetaldoxime to the (Z)-isomer, which blocks the route towards cyanogenic glucoside synthesis
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additional information
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CYP83B1 cannot convert the (E)-p-hydroxyphenylacetaldoxime to the (Z)-isomer, which blocks the route towards cyanogenic glucoside synthesis. Instead CYP83B1 catalyzes the conversion of the (E)-p-hydroxyphenylacetaldoxime into an S-alkyl-thiohydroximate with retention of the configuration of the E-oxime intermediate in the final glucosinolate core structure
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additional information
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CYP83B1 metabolizes aliphatic oximes with very low efficiency
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additional information
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isoform CYP83A1 catalyzes the initial conversion of aldoximes to thiohydroximates in the synthesis of glucosinolates not derived from tryptophan
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