1.14.14.36: tyrosine N-monooxygenase
This is an abbreviated version!
For detailed information about tyrosine N-monooxygenase, go to the full flat file.
Word Map on EC 1.14.14.36
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1.14.14.36
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sorghum
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glucoside
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dhurrin
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bicolor
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cyp71e1
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glucosinolate
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oxime
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moench
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nitril
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aldoximes
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p-hydroxyphenylacetaldoxime
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p-hydroxymandelonitrile
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leucine-derived
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ugt85b1
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udp-glucosyltransferase
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c-hydroxylation
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phenylacetaldoxime
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tyrosine-derived
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linamarin
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n-hydroxytyrosine
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agriculture
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p-hydroxyphenylacetaldehyde
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biotechnology
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indole-3-acetaldoxime
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lotaustralin
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analysis
- 1.14.14.36
- sorghum
- glucoside
- dhurrin
- bicolor
- cyp71e1
- glucosinolate
- oxime
- moench
-
nitril
- aldoximes
- p-hydroxyphenylacetaldoxime
- p-hydroxymandelonitrile
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leucine-derived
- ugt85b1
- udp-glucosyltransferase
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c-hydroxylation
- phenylacetaldoxime
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tyrosine-derived
- linamarin
- n-hydroxytyrosine
- agriculture
- p-hydroxyphenylacetaldehyde
- biotechnology
- indole-3-acetaldoxime
- lotaustralin
- analysis
Reaction
+ 2 O2 + 2 [reduced NADPH-hemoprotein reductase] = + 2 [oxidized NADPH-hemoprotein reductase] + + 3 H2O
Synonyms
CYP79, CYP79A1, cytochrome P-450tyr, cytochrome P450 CYP79E1, cytochrome P450 CYP79E2, Cytochrome P450Tyr, EC 1.14.13.41, P450Tyr, tyrosine N-hydroxylase, Tyrosine N-monooxygenase
ECTree
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Substrates Products
Substrates Products on EC 1.14.14.36 - tyrosine N-monooxygenase
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REACTION DIAGRAM
1-nitro-2-(4-hydroxyphenyl)ethane + O2 + [reduced NADPH-hemoprotein reductase]
N,N-dihydroxy-L-tyrosine + [oxidized NADPH-hemoprotein reductase] + H2O
involvement of 1-nitro-2-(4-hydroxyphenyl)ethane or more likely its aci-nitro tautomer as an intermediate between N-hydroxytyrosine and 4-hydroxyphenylacetaldehyde oxime
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-
?
L-tyrosine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
(E)-[4-hydroxyphenylacetaldehyde oxime] + 2 [oxidized NADPH-hemoprotein reductase] + CO2 + 3 H2O
L-tyrosine + O2 + NADPH + H+
N-hydroxy-L-tyrosine + NADP+ + H2O
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r
L-tyrosine + O2 + [reduced NADPH-hemoprotein reductase]
N-hydroxy-L-tyrosine + [oxidized NADPH-hemoprotein reductase] + H2O
N,N-dihydroxy-L-tyrosine
(E)-[4-hydroxyphenylacetaldehyde oxime] + CO2 + H2O
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?
N-hydroxy-L-tyrosine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
N,N-dihydroxy-L-tyrosine + [oxidized NADPH-hemoprotein reductase] + H2O
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?
N-hydroxy-L-tyrosine + O2 + [reduced NADPH-hemoprotein reductase]
N,N-dihydroxy-L-tyrosine + [oxidized NADPH-hemoprotein reductase] + H2O
(E)-[4-hydroxyphenylacetaldehyde oxime] + 2 [oxidized NADPH-hemoprotein reductase] + CO2 + 3 H2O
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?
L-tyrosine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
(E)-[4-hydroxyphenylacetaldehyde oxime] + 2 [oxidized NADPH-hemoprotein reductase] + CO2 + 3 H2O
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?
L-tyrosine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
(E)-[4-hydroxyphenylacetaldehyde oxime] + 2 [oxidized NADPH-hemoprotein reductase] + CO2 + 3 H2O
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overall reaction
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?
L-tyrosine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
(E)-[4-hydroxyphenylacetaldehyde oxime] + 2 [oxidized NADPH-hemoprotein reductase] + CO2 + 3 H2O
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overall reaction. NADPH is a much better cofactor for NADPH-hemoprotein reductase than NADH although NADH does support the entire catalytic cycle
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?
L-tyrosine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
(E)-[4-hydroxyphenylacetaldehyde oxime] + 2 [oxidized NADPH-hemoprotein reductase] + CO2 + 3 H2O
intermediate products: N-hydroxytyrosine, N,N-dihydroxytyrosine, (E)-p-hydroxyphenylacetaldoxime
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?
L-tyrosine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
(E)-[4-hydroxyphenylacetaldehyde oxime] + 2 [oxidized NADPH-hemoprotein reductase] + CO2 + 3 H2O
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overall reaction, P450Tyr is a multifunctional tyrosine N-hydroxylase catalyzing the double N-hydroxylation of L-tyrosine to N,N-dihydroxy-L-tyrosine which dehydrates and decarboxylates to 4-hydroxyphenylacetaldoxime
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?
L-tyrosine + 2 O2 + 2 [reduced NADPH-hemoprotein reductase]
(E)-[4-hydroxyphenylacetaldehyde oxime] + 2 [oxidized NADPH-hemoprotein reductase] + CO2 + 3 H2O
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?
N-hydroxy-L-tyrosine + [oxidized NADPH-hemoprotein reductase] + H2O
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?
L-tyrosine + O2 + [reduced NADPH-hemoprotein reductase]
N-hydroxy-L-tyrosine + [oxidized NADPH-hemoprotein reductase] + H2O
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?
L-tyrosine + O2 + [reduced NADPH-hemoprotein reductase]
N-hydroxy-L-tyrosine + [oxidized NADPH-hemoprotein reductase] + H2O
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-
?
L-tyrosine + O2 + [reduced NADPH-hemoprotein reductase]
N-hydroxy-L-tyrosine + [oxidized NADPH-hemoprotein reductase] + H2O
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?
L-tyrosine + O2 + [reduced NADPH-hemoprotein reductase]
N-hydroxy-L-tyrosine + [oxidized NADPH-hemoprotein reductase] + H2O
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high substrate specificity
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?
L-tyrosine + O2 + [reduced NADPH-hemoprotein reductase]
N-hydroxy-L-tyrosine + [oxidized NADPH-hemoprotein reductase] + H2O
enzyme in biosynthesis of cyanogenic glucosides
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?
L-tyrosine + O2 + [reduced NADPH-hemoprotein reductase]
N-hydroxy-L-tyrosine + [oxidized NADPH-hemoprotein reductase] + H2O
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enzyme in biosynthesis of cyanogenic glucosides
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?
L-tyrosine + O2 + [reduced NADPH-hemoprotein reductase]
N-hydroxy-L-tyrosine + [oxidized NADPH-hemoprotein reductase] + H2O
enzyme in biosynthesis of cyanogenic glucosides
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?
L-tyrosine + O2 + [reduced NADPH-hemoprotein reductase]
N-hydroxy-L-tyrosine + [oxidized NADPH-hemoprotein reductase] + H2O
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enzyme in biosynthesis of cyanogenic glucosides
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-
?
N,N-dihydroxy-L-tyrosine + [oxidized NADPH-hemoprotein reductase] + H2O
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?
N-hydroxy-L-tyrosine + O2 + [reduced NADPH-hemoprotein reductase]
N,N-dihydroxy-L-tyrosine + [oxidized NADPH-hemoprotein reductase] + H2O
involvement of 1-nitro-2-(4-hydroxyphenyl)ethane or more likely its aci-nitro tautomer as an intermediate between N-hydroxytyrosine and 4-hydroxyphenylacetaldehyde oxime
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?
?
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P450Tyr does not metabolize L-phenylalanine
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?
additional information
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CYP79A1 has a very high substrate specificity, tyrosine being the only substrate found. Analogs 1-nitro-2-p-(hydroxyphenyl)ethane, N-hydroxytyrosine and phenylalanine are able to bind to the enzyme, without being metabolized
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additional information
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CYP79A1 has a very high substrate specificity, tyrosine being the only substrate found. Analogs 1-nitro-2-p-(hydroxyphenyl)ethane, N-hydroxytyrosine and phenylalanine are able to bind to the enzyme, without being metabolized
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?
additional information
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product of the second N-hydroxylation reaction is N,N-dihydroxytyrosine. N,N-dihydroxytyrosine is dehydrated to 2-nitroso-3-(4-hydroxyphenyl) propionic acid which decarboxylates to p-hydroxyphenylacetaldehyde oxime. The dehydration and decarboxylation reactions may proceed non-enzymatically. The E/Z ratio of the p-hydroxyphenylacetaldehyde oxime produced by reconstituted cytochrome P450Tyr is 69:31. Binding of L-tyrosine or N-hydroxytyrosine mutually excludes binding of the other substrate
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additional information
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product of the second N-hydroxylation reaction is N,N-dihydroxytyrosine. N,N-dihydroxytyrosine is dehydrated to 2-nitroso-3-(4-hydroxyphenyl) propionic acid which decarboxylates to p-hydroxyphenylacetaldehyde oxime. The dehydration and decarboxylation reactions may proceed non-enzymatically. The E/Z ratio of the p-hydroxyphenylacetaldehyde oxime produced by reconstituted cytochrome P450Tyr is 69:31. Binding of L-tyrosine or N-hydroxytyrosine mutually excludes binding of the other substrate
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additional information
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no substrate: L-3,4-Dihydroxyphenyl-alanine, i.e. DOPA
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additional information
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no substrate: L-3,4-Dihydroxyphenyl-alanine, i.e. DOPA
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additional information
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no substrate: L-3,4-Dihydroxyphenyl-alanine, i.e. DOPA
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