KEGG   ORTHOLOGY: K13027
Entry
K13027                      KO                                     

Name
CYP79A1
Definition
tyrosine N-monooxygenase [EC:1.14.14.36]
Pathway
ko00460  Cyanoamino acid metabolism
ko00966  Glucosinolate biosynthesis
ko01100  Metabolic pathways
ko01110  Biosynthesis of secondary metabolites
ko01210  2-Oxocarboxylic acid metabolism
Module
M00369  Cyanogenic glycoside biosynthesis, tyrosine => dhurrin
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09106 Metabolism of other amino acids
   00460 Cyanoamino acid metabolism
    K13027  CYP79A1; tyrosine N-monooxygenase
  09110 Biosynthesis of other secondary metabolites
   00966 Glucosinolate biosynthesis
    K13027  CYP79A1; tyrosine N-monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K13027  CYP79A1; tyrosine N-monooxygenase
Enzymes [BR:ko01000]
 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
    1.14.14.36  tyrosine N-monooxygenase
     K13027  CYP79A1; tyrosine N-monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP79 family
   K13027  CYP79A1; tyrosine N-monooxygenase
Other DBs
RN: R00730 R04460 R07190 R10671
GO: 0050370
Genes
BDI: 100844710
ATS: 109784188(LOC109784188)
SBI: 8061413 8061994
ZMA: 103638611
SITA: 101771875 101781613
Reference
PMID:7487064
  Authors
Koch BM, Sibbesen O, Halkier BA, Svendsen I, Moller BL
  Title
The primary sequence of cytochrome P450tyr, the multifunctional N-hydroxylase catalyzing the conversion of L-tyrosine to p-hydroxyphenylacetaldehyde oxime in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench.
  Journal
Arch Biochem Biophys 323:177-86 (1995)
DOI:10.1006/abbi.1995.0024
  Sequence
[sbi:8061413]

KEGG   ENZYME: 1.14.14.36
Entry
EC 1.14.14.36               Enzyme                                 

Name
tyrosine N-monooxygenase;
tyrosine N-hydroxylase;
CYP79A1
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
Sysname
L-tyrosine,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (N-hydroxylating)
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]
Reaction(KEGG)
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]
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]
Comment
A cytochrome P-450 (heme-thiolate) protein. The enzyme from Sorghum is involved in the biosynthesis of the cyanogenic glucoside dhurrin. In Sinapis alba (white mustard) the enzyme is involved in the biosynthesis of the glucosinolate sinalbin.
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
Pathway
ec00460  Cyanoamino acid metabolism
ec00966  Glucosinolate biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K13027  tyrosine N-monooxygenase
K20785  tyrosine N-monooxygenase
Genes
BDI: 100844710
ATS: 109784188(LOC109784188)
SBI: 8061413 8061994
ZMA: 103638611
SITA: 101771875 101781613
Reference
1  [PMID:2250015]
  Authors
Halkier BA, Moller BL.
  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.
  Journal
J Biol Chem 265:21114-21 (1990)
Reference
2  [PMID:7876084]
  Authors
Sibbesen O, Koch B, Halkier BA, Moller BL.
  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.
  Journal
J Biol Chem 270:3506-11 (1995)
DOI:10.1074/jbc.270.8.3506
Reference
3  [PMID:12223771]
  Authors
Bennett RN, Kiddle G, Wallsgrove RM.
  Title
Involvement of Cytochrome P450 in Glucosinolate Biosynthesis in White Mustard (A Biochemical Anomaly).
  Journal
Plant Physiol 114:1283-1291 (1997)
DOI:10.1104/pp.114.4.1283
Reference
4  [PMID:10049494]
  Authors
Kahn RA, Fahrendorf T, Halkier BA, Moller BL.
  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.
  Journal
Arch Biochem Biophys 363:9-18 (1999)
DOI:10.1006/abbi.1998.1068
Reference
5  [PMID:10938360]
  Authors
Bak S, Olsen CE, Halkier BA, Moller BL.
  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.
  Journal
Plant Physiol 123:1437-48 (2000)
DOI:10.1104/pp.123.4.1437
Reference
6  [PMID:10759528]
  Authors
Nielsen JS, Moller BL.
  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.
  Journal
Plant Physiol 122:1311-21 (2000)
DOI:10.1104/pp.122.4.1311
  Sequence
Reference
7  [PMID:12114576]
  Authors
Busk PK, Moller BL.
  Title
Dhurrin synthesis in sorghum is regulated at the transcriptional level and induced by nitrogen fertilization in older plants.
  Journal
Plant Physiol 129:1222-31 (2002)
DOI:10.1104/pp.000687
Reference
8  [PMID:15665094]
  Authors
Kristensen C, Morant M, Olsen CE, Ekstrom CT, Galbraith DW, Moller BL, Bak S.
  Title
Metabolic engineering of dhurrin in transgenic Arabidopsis plants with marginal inadvertent effects on the metabolome and transcriptome.
  Journal
Proc Natl Acad Sci U S A 102:1779-84 (2005)
DOI:10.1073/pnas.0409233102
Reference
9  [PMID:26361733]
  Authors
Clausen M, Kannangara RM, Olsen CE, Blomstedt CK, Gleadow RM, Jorgensen K, Bak S, Motawie MS, Moller BL
  Title
The bifurcation of the cyanogenic glucoside and glucosinolate biosynthetic pathways.
  Journal
Plant J 84:558-73 (2015)
DOI:10.1111/tpj.13023
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.36
IUBMB Enzyme Nomenclature: 1.14.14.36
ExPASy - ENZYME nomenclature database: 1.14.14.36
BRENDA, the Enzyme Database: 1.14.14.36
CAS: 159447-19-5

KEGG   REACTION: R04460
Entry
R04460                      Reaction                               

Name
N-hydroxy-L-tyrosine,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (N-hydroxylating)
Definition
N-Hydroxy-L-tyrosine + Oxygen + [Reduced NADPH---hemoprotein reductase] <=> N,N-Dihydroxy-L-tyrosine + [Oxidized NADPH---hemoprotein reductase] + H2O
Equation
Comment
first step of two-step reaction (R04460+R07190 or R06585), subsequently R07190
and second step of three-step reaction (see R10671, R00730+R04460+R07190)
Reaction class
RC00001  C00005_C00006
RC01918  C03004_C15503
Enzyme
Pathway
rn00460  Cyanoamino acid metabolism
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00369  Cyanogenic glycoside biosynthesis, tyrosine => dhurrin
Orthology
K13027  tyrosine N-monooxygenase [EC:1.14.14.36]
Other DBs
RHEA: 24063

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