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

S-[(E)-N-hydroxy(indol-3-yl)acetimidoyl]-L-glutathione

+ 2 H2O

Synonyms

At4g31500, CYP83B1, cytochrome P450 83B1, HM347235

ECTree

1 Oxidoreductases

1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen

1.14.14 With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor

1.14.14.45 aromatic aldoxime N-monooxygenase

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2	AA Sequence
5	Cloned(Commentary)
2	Cofactor
10	General Information
3	Inhibitors
3	kcat/KM [mM/s]
7	KM Value [mM]
8	Natural Substrates/ Products (Substrates)
12	Organism
4	Pathway
1	pH Optimum
6	Reaction
12	Reference
3	Source Tissue
22	Substrates and Products (Substrate)
12	Synonyms
1	Systematic Name
9	Turnover Number [1/s]

Natural Substrates Products

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Natural Substrates Products on EC 1.14.14.45 - aromatic aldoxime N-monooxygenase

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(E)-4-hydroxyphenylacetaldoxime + O2 + [reduced NADPH-hemoprotein reductase]

1-aci-nitro-2-(4-hydroxyphenyl)-ethane + H2O + [oxidized NADPH-hemoprotein reductase]

Arabidopsis thaliana

O65782

743473

(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

Arabidopsis thaliana

O65782

741195

overall reaction

(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

Arabidopsis thaliana

O65782

741195

overall reaction

(E)-phenylacetaldehyde oxime + [reduced NADPH-hemoprotein reductase] + glutathione + O2

S-[(Z)-N-hydroxy(phenyl)acetimidoyl]-L-glutathione + [oxidized NADPH-hemoprotein reductase] + 2 H2O

Arabidopsis thaliana

O65782

741195

overall reaction

1-aci-nitro-2-(4-hydroxyphenyl)-ethane + 2-mercaptoethanol

(Z)-2-hydroxyethyl N-hydroxy-2-(4-hydroxyphenyl)ethanimidothioate + H2O

Arabidopsis thaliana

O65782

743473

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]

Arabidopsis thaliana

O65782

743473

indole-3-acetaldoxime + [reduced NADPH-hemoprotein reductase] + O2

1-aci-nitro-2-indolyl-ethane + [oxidized NADPH-hemoprotein reductase] + 2 H2O

Arabidopsis thaliana

O65782

741148

the aci-nitro compound formed reacts non-enzymatically with thiol compounds to produce an N-alkyl-thiohydroximate adduct, the committed precursor of glucosinolates

additional information

Arabidopsis thaliana

O65782

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

743473