KEGG ORTHOLOGY: K13027

ORTHOLOGY: K13027

Entry

K13027                      KO

Symbol

CYP79A1

Name

tyrosine N-monooxygenase [EC:1.14.14.36]

Pathway

map00460

Cyanoamino acid metabolism

map00966

Glucosinolate biosynthesis

map01100

Metabolic pathways

map01110

Biosynthesis of secondary metabolites

map01210

2-Oxocarboxylic acid metabolism

Module

M00369

Cyanogenic glycoside biosynthesis, tyrosine => dhurrin

Reaction

R00730

L-tyrosine,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (N-hydroxylating)

R04460

N-hydroxy-L-tyrosine,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (N-hydroxylating)

R07190

R10671

L-tyrosine,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (N-hydroxylating)

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

GO:

0050370

Genes

CPAP:

110808696

RARG:

115733146

CSAV:

115700392 115700877

MOF:	131159634 131159913 131160740 131160782 131160786

MING:

122082619

BDI:	100844404 100844710

ATS:	109735617 109735773 109761069 109761668 109761669 109761674 109762566 109773788 109784188 109784348

TUA:	125516067 125516660 125518600 125524712 125525533 125525885 125548685 125554390

LPER:

127306207 127309770 127338618 127338620 127344010 127344055 127344577

LRD:	124662858 124681626 124689323 124690145 124693633

SBI:	8061413 8061994

ZMA:

103638611

MFLO:

136517999 136518043 136522148 136522421 136523023 136537578 136537639

SITA:

101771875 101781613

SVS:	117851946 117853679

PVIR:

120668766 120669225 120671567

PHAI:

112889966

PAUA:

133915009

ZOF:	121977720 122011939 122013738 122017325

ACAK:

137966491

» show all

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]

All links

Ontology (1)   
   GO (1)   
Gene (1)   
   OC (1)   
All databases (2)   

Download RDF

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)

R00730 R04460 R07190 R10671

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

CPAP:

110808696

RARG:

115733146

CSAV:

115700392 115700877

MOF:	131159634 131159913 131160740 131160782 131160786

MING:

122082619

BDI:	100844404 100844710

ATS:	109735617 109735773 109761069 109761668 109761669 109761674 109762566 109773788 109784188 109784348

TDC:	119283854 119310652 119310656 119315677 119315988 119322151 119322220 119322360 119322455 119322484 119323745 119323781 119325453 119325576 119326042 119326092 119328753 119333344 119334570 119339130 119346579 119346580 119346581 119346582 119346584 119347383 119349993 119359139 119367488

TAES:

123039366 123040956 123048979 123058645 123074835 123082655 123115314 123115317 123121204 123126171 123129465 123129689 123130256 123133566 123133567 123133663 123138575 123138576 123141446 123153217 123153556 123153558 123158178 123167847 123170371 123171291 123184966

TUA:	125516067 125516660 125518600 125524712 125525533 125525885 125548685 125554390

LPER:

127306207 127309770 127338618 127338620 127344010 127344055 127344577

LRD:	124662858 124681626 124689323 124690145 124693633

SBI:	8061413 8061994

ZMA:

103638611

MFLO:

136517999 136518043 136522148 136522421 136523023 136537578 136537639

SITA:

101771875 101781613

SVS:	117851946 117853679

PVIR:

120668766 120669225 120671567

PHAI:

112889966

PAUA:

133915009

ZOF:	121977720 122011939 122013738 122017325

ACAK:

137966491

» show all

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

[ag:AAF66543 AAF66544]

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

All links

Protein sequence (6)   
   UniProt (4)   
   SWISS-PROT (1)   
   RefSeq(pep) (1)   
DNA sequence (3)   
   RefSeq(nuc) (1)   
   GenBank (1)   
   EMBL (1)   
Protein domain (4)   
   InterPro (4)   
All databases (13)   

Download RDF

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

C03004 + C00007 + C03024 <=> C15503 + C03161 + C00001

Comment

the first step of two-step reaction (R04460+R07190 or R06585), subsequently R07190
the second step of three-step reaction (see R10671, R00730+R04460+R07190)

Reaction class

RC00001

C00005_C00006

RC01918

C03004_C15503

Enzyme

1.14.14.36

Pathway

rn00460

Cyanoamino acid metabolism

rn01100

Metabolic pathways

rn01110

Biosynthesis of secondary metabolites

Module

M00369

Cyanogenic glycoside biosynthesis, tyrosine => dhurrin

Brite

Enzymatic reactions [BR:br08201]
1. Oxidoreductase reactions
  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
     R04460  N-Hydroxy-L-tyrosine + Oxygen + [Reduced NADPH---hemoprotein reductase] <=> N,N-Dihydroxy-L-tyrosine + [Oxidized NADPH---hemoprotein reductase] + H2O

Orthology

K13027

tyrosine N-monooxygenase [EC:1.14.14.36]

Other DBs

RHEA:

24063

All links

No link information was found.

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