| Entry |
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| Name |
tyrosine N-monooxygenase;
tyrosine N-hydroxylase;
CYP79A1
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| 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
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| Sysname |
L-tyrosine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (N-hydroxylating)
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| Reaction(IUBMB) |
L-tyrosine + 2 O2 + 2 [reduced NADPH---hemoprotein reductase] = (E)-[4-hydroxyphenylacetaldehyde oxime] + 2 [oxidized NADPH---hemoprotein reductase] + CO2 + 3 H2O (overall reaction) [RN: R10671];
(1a) L-tyrosine + O2 + [reduced NADPH---hemoprotein reductase] = N-hydroxy-L-tyrosine + [oxidized NADPH---hemoprotein reductase] + H2O [RN: R00730];
(1b) N-hydroxy-L-tyrosine + O2 + [reduced NADPH---hemoprotein reductase] = N,N-dihydroxy-L-tyrosine + [oxidized NADPH---hemoprotein reductase] + H2O [RN: R04460];
(1c) N,N-dihydroxy-L-tyrosine = (E)-[4-hydroxyphenylacetaldehyde oxime] + CO2 + H2O [RN: R07190]
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| Reaction(KEGG) |
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| Substrate |
L-tyrosine [CPD: C00082];
O2 [CPD: C00007];
[reduced NADPH---hemoprotein reductase] [CPD: C03024];
N-hydroxy-L-tyrosine [CPD: C03004];
N,N-dihydroxy-L-tyrosine [CPD: C15503]
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| Product |
(E)-[4-hydroxyphenylacetaldehyde oxime] [CPD: C04350];
[oxidized NADPH---hemoprotein reductase] [CPD: C03161];
CO2 [CPD: C00011];
H2O [CPD: C00001];
N-hydroxy-L-tyrosine [CPD: C03004];
N,N-dihydroxy-L-tyrosine [CPD: C15503]
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| Comment |
A cytochrome P-450 (heme-thiolate) protein. The enzyme is involved in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum, along with EC 1.14.14.37, 4-hydroxyphenylacetaldehyde oxime monooxygenase and EC 2.4.1.85, cyanohydrin beta-glucosyltransferase. Some 2-(4-hydroxyphenyl)-1-nitroethane is formed as a side product.
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| History |
EC 1.14.14.36 created 1992 as EC 1.14.13.41, modified 2001, modified 2005, transferred 2016 to EC 1.14.14.36
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| Pathway |
| Cyanoamino acid metabolism | | Glucosinolate biosynthesis | | Biosynthesis of secondary metabolites |
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| Orthology |
| tyrosine N-monooxygenase | | tyrosine N-monooxygenase |
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| Genes |
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| Reference |
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| Authors |
Halkier BA, Moller BL. |
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| Title |
The biosynthesis of cyanogenic glucosides in higher plants. Identification of three hydroxylation steps in the biosynthesis of dhurrin in Sorghum bicolor (L.) Moench and the involvement of 1-ACI-nitro-2-(p-hydroxyphenyl)ethane as an intermediate. |
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| Journal |
J. Biol. Chem. 265 (1990) 21114-21. |
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| Reference |
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| Authors |
Sibbesen O, Koch B, Halkier BA, Moller BL. |
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| Title |
Cytochrome P-450TYR is a multifunctional heme-thiolate enzyme catalyzing the conversion of L-tyrosine to p-hydroxyphenylacetaldehyde oxime in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench. |
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| Journal |
J. Biol. Chem. 270 (1995) 3506-11. |
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| Reference |
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| Authors |
Kahn RA, Fahrendorf T, Halkier BA, Moller BL. |
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| Title |
Substrate specificity of the cytochrome P450 enzymes CYP79A1 and CYP71E1 involved in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench. |
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| Journal |
Arch. Biochem. Biophys. 363 (1999) 9-18. |
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| Reference |
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| Authors |
Bak S, Olsen CE, Halkier BA, Moller BL. |
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| Title |
Transgenic tobacco and Arabidopsis plants expressing the two multifunctional sorghum cytochrome P450 enzymes, CYP79A1 and CYP71E1, are cyanogenic and accumulate metabolites derived from intermediates in Dhurrin biosynthesis. |
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| Journal |
Plant. Physiol. 123 (2000) 1437-48. |
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| Reference |
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| Authors |
Nielsen JS, Moller BL. |
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| Title |
Cloning and expression of cytochrome P450 enzymes catalyzing the conversion of tyrosine to p-hydroxyphenylacetaldoxime in the biosynthesis of cyanogenic glucosides in Triglochin maritima. |
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| Journal |
Plant. Physiol. 122 (2000) 1311-21. |
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| Sequence |
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| Reference |
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| Authors |
Busk PK, Moller BL. |
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| Title |
Dhurrin synthesis in sorghum is regulated at the transcriptional level and induced by nitrogen fertilization in older plants. |
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| Journal |
Plant. Physiol. 129 (2002) 1222-31. |
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| Reference |
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| Authors |
Kristensen C, Morant M, Olsen CE, Ekstrom CT, Galbraith DW, Moller BL, Bak S. |
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| Title |
Metabolic engineering of dhurrin in transgenic Arabidopsis plants with marginal inadvertent effects on the metabolome and transcriptome. |
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| Journal |
Proc. Natl. Acad. Sci. U. S. A. 102 (2005) 1779-84. |
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| Reference |
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| Authors |
Clausen M, Kannangara RM, Olsen CE, Blomstedt CK, Gleadow RM, Jorgensen K, Bak S, Motawie MS, Moller BL |
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| Title |
The bifurcation of the cyanogenic glucoside and glucosinolate biosynthetic pathways. |
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| Journal |
Plant. J. 84 (2015) 558-73. |
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| Other DBs |
ExplorEnz - The Enzyme Database: IUBMB Enzyme Nomenclature: ExPASy - ENZYME nomenclature database: BRENDA, the Enzyme Database: CAS: 159447-19-5 |
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| LinkDB |
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