KEGG ORTHOLOGY: K11812

ORTHOLOGY: K11812

Entry

K11812                      KO

Symbol

CYP79B1_2

Name

tryptophan N-monooxygenase [EC:1.14.14.156]

Pathway

map00380

Tryptophan metabolism

map00966

Glucosinolate biosynthesis

map01100

Metabolic pathways

map01110

Biosynthesis of secondary metabolites

map01210

2-Oxocarboxylic acid metabolism

Module

M00370

Glucosinolate biosynthesis, tryptophan => glucobrassicin

Reaction

R08160

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

Brite

KEGG Orthology (KO) [BR:ko00001]
09100 Metabolism
  09105 Amino acid metabolism
   00380 Tryptophan metabolism
    K11812  CYP79B1_2; tryptophan N-monooxygenase
  09110 Biosynthesis of other secondary metabolites
   00966 Glucosinolate biosynthesis
    K11812  CYP79B1_2; tryptophan N-monooxygenase
09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K11812  CYP79B1_2; tryptophan 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
    1.14.14.156  tryptophan N-monooxygenase
     K11812  CYP79B1_2; tryptophan N-monooxygenase
Cytochrome P450 [BR:ko00199]
Cytochrome P450, plant type
  CYP79 family
   K11812  CYP79B1_2; tryptophan N-monooxygenase

Genes

ATH:	AT4G39950(CYP79B2)

ALY:

9302968

CRB:

17879334

CSAT:

104716281 104720922 104729322 104729349

EUS:	EUTSA_v10000278mg EUTSA_v10024861mg

BRP:	103835554 103853878 103862605

BNA:	106361376 106382592 106410467 106439341 106441279 125580497 125584456

BOE:	106301717 106302779 106330945

RSZ:	108818790 108819835 108830725 108855674 130507033 130507293 130507697 130511890

THJ:	104804164 104807687

TDC:

119320796

» show all

Reference

PMID:10922360 (CYP79B2)

Authors

Mikkelsen MD, Hansen CH, Wittstock U, Halkier BA

Title

Cytochrome P450 CYP79B2 from Arabidopsis catalyzes the conversion of tryptophan to indole-3-acetaldoxime, a precursor of indole glucosinolates and indole-3-acetic acid.

Journal

J Biol Chem 275:33712-7 (2000)
DOI:10.1074/jbc.M001667200

Sequence

[ath:AT4G39950]

Reference

PMID:12464264 (CYP79B5)

Authors

Naur P, Hansen CH, Bak S, Hansen BG, Jensen NB, Nielsen HL, Halkier BA

Title

CYP79B1 from Sinapis alba converts tryptophan to indole-3-acetaldoxime.

Journal

Arch Biochem Biophys 409:235-41 (2003)
DOI:10.1016/S0003-9861(02)00567-2

Sequence

[brp:103853878]

LinkDB

ORTHOLOGY: K11813

Entry

K11813                      KO

Symbol

CYP79B3

Name

tryptophan N-monooxygenase [EC:1.14.14.156]

Pathway

map00380

Tryptophan metabolism

map00966

Glucosinolate biosynthesis

map01100

Metabolic pathways

map01110

Biosynthesis of secondary metabolites

map01210

2-Oxocarboxylic acid metabolism

Module

M00370

Glucosinolate biosynthesis, tryptophan => glucobrassicin

Reaction

R08160

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

Brite

KEGG Orthology (KO) [BR:ko00001]
09100 Metabolism
  09105 Amino acid metabolism
   00380 Tryptophan metabolism
    K11813  CYP79B3; tryptophan N-monooxygenase
  09110 Biosynthesis of other secondary metabolites
   00966 Glucosinolate biosynthesis
    K11813  CYP79B3; tryptophan N-monooxygenase
09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K11813  CYP79B3; tryptophan 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
    1.14.14.156  tryptophan N-monooxygenase
     K11813  CYP79B3; tryptophan N-monooxygenase
Cytochrome P450 [BR:ko00199]
Cytochrome P450, plant type
  CYP79 family
   K11813  CYP79B3; tryptophan N-monooxygenase

Genes

ATH:	AT2G22330(CYP79B3)

ALY:

9314677

CRB:

17889834

CSAT:

104702772 104713678 104751874

EUS:	EUTSA_v10000114mg

BRP:

BNA:

BOE:

RSZ:

THJ:

TDC:

Reference

PMID:10681464

Authors

Hull AK, Vij R, Celenza JL

Title

Arabidopsis cytochrome P450s that catalyze the first step of tryptophan-dependent indole-3-acetic acid biosynthesis.

Journal

Proc Natl Acad Sci U S A 97:2379-84 (2000)
DOI:10.1073/pnas.040569997

Sequence

[ath:AT2G22330]

LinkDB

ENZYME: 1.14.14.156

Entry

EC 1.14.14.156              Enzyme

Name

tryptophan N-monooxygenase;
tryptophan N-hydroxylase;
CYP79B1;
CYP79B2;
CYP79B3

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

Reaction(IUBMB)

L-tryptophan + 2 [reduced NADPH---hemoprotein reductase] + 2 O2 = (E)-indol-3-ylacetaldoxime + 2 [oxidized NADPH---hemoprotein reductase] + CO2 + 3 H2O (overall reaction) [RN:R08160];
(1a) L-tryptophan + [reduced NADPH---hemoprotein reductase] + O2 = N-hydroxy-L-tryptophan + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R09583];
(1b) N-hydroxy-L-tryptophan + [reduced NADPH---hemoprotein reductase] + O2 = N,N-dihydroxy-L-tryptophan + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R09584];
(1c) N,N-dihydroxy-L-tryptophan = (E)-indol-3-ylacetaldoxime + CO2 + H2O [RN:R09585]

Reaction(KEGG)

R08160 R09583 R09584 R09585

Substrate

L-tryptophan [CPD:C00078];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007];
N-hydroxy-L-tryptophan [CPD:C19716];
N,N-dihydroxy-L-tryptophan [CPD:C19717]

Product

(E)-indol-3-ylacetaldoxime [CPD:C02937];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
CO2 [CPD:C00011];
H2O [CPD:C00001];
N-hydroxy-L-tryptophan [CPD:C19716];
N,N-dihydroxy-L-tryptophan [CPD:C19717]

Comment

A cytochrome P-450 (heme-thiolate) protein from the plant Arabidopsis thaliana. This enzyme catalyses two successive N-hydroxylations of L-tryptophan, the first steps in the biosynthesis of both auxin and the indole alkaloid phytoalexin camalexin. The product of the two hydroxylations, N,N-dihydroxy-L-tryptophan, is extremely labile and dehydrates spontaneously. The dehydrated product is then subject to a decarboxylation that produces an oxime. It is still not known whether the decarboxylation is spontaneous or catalysed by the enzyme.

History

EC 1.14.14.156 created 2011 as EC 1.14.13.125, transferred 2018 to EC 1.14.14.156

Pathway

ec00380

Tryptophan metabolism

ec00966

Glucosinolate biosynthesis

ec01100

Metabolic pathways

ec01110

Biosynthesis of secondary metabolites

Orthology

K11812

tryptophan N-monooxygenase

K11813

tryptophan N-monooxygenase

Genes

ATH:	AT2G22330(CYP79B3) AT4G39950(CYP79B2)

ALY:	9302968 9314677

CRB:	17879334 17889834

CSAT:

104702772 104713678 104716281 104720922 104729322 104729349 104751874

EUS:	EUTSA_v10000114mg EUTSA_v10000278mg EUTSA_v10024861mg

BRP:	103835554 103853878 103862605 103864341

BNA:	106361376 106382592 106410467 106439341 106441279 106446405 125580497 125584456

BOE:	106301717 106302779 106330945 106337668

RSZ:	108818790 108819835 108830725 108854183 108855674 130507033 130507293 130507697 130511890

THJ:	104804164 104807687 104824879

TDC:	119320796 119348157

» show all

Reference

1 [PMID:10922360]

Authors

Mikkelsen MD, Hansen CH, Wittstock U, Halkier BA

Title

Cytochrome P450 CYP79B2 from Arabidopsis catalyzes the conversion of tryptophan to indole-3-acetaldoxime, a precursor of indole glucosinolates and indole-3-acetic acid.

Journal

J Biol Chem 275:33712-7 (2000)
DOI:10.1074/jbc.M001667200

Sequence

[ath:AT4G39950]

Reference

2 [PMID:10681464]

Authors

Hull AK, Vij R, Celenza JL

Title

Arabidopsis cytochrome P450s that catalyze the first step of tryptophan-dependent indole-3-acetic acid biosynthesis.

Journal

Proc Natl Acad Sci U S A 97:2379-84 (2000)
DOI:10.1073/pnas.040569997

Sequence

[ath:AT4G39950 AT2G22330]

Reference

3 [PMID:12464638]

Authors

Zhao Y, Hull AK, Gupta NR, Goss KA, Alonso J, Ecker JR, Normanly J, Chory J, Celenza JL

Title

Trp-dependent auxin biosynthesis in Arabidopsis: involvement of cytochrome P450s CYP79B2 and CYP79B3.

Journal

Genes Dev 16:3100-12 (2002)
DOI:10.1101/gad.1035402

Reference

4 [PMID:12464264]

Authors

Naur P, Hansen CH, Bak S, Hansen BG, Jensen NB, Nielsen HL, Halkier BA

Title

CYP79B1 from Sinapis alba converts tryptophan to indole-3-acetaldoxime.

Journal

Arch Biochem Biophys 409:235-41 (2003)
DOI:10.1016/S0003-9861(02)00567-2

Sequence

[brp:103853878]

Other DBs

ExplorEnz - The Enzyme Database:

1.14.14.156

IUBMB Enzyme Nomenclature:

1.14.14.156

ExPASy - ENZYME nomenclature database:

1.14.14.156

BRENDA, the Enzyme Database:

1.14.14.156

LinkDB

REACTION: R08160

Entry

R08160                      Reaction

Name

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

Definition

L-Tryptophan + 2 [Reduced NADPH---hemoprotein reductase] + 2 Oxygen <=> Indole-3-acetaldehyde oxime + 2 [Oxidized NADPH---hemoprotein reductase] + CO2 + 3 H2O

Equation

C00078 + 2 C03024 + 2 C00007 <=> C02937 + 2 C03161 + C00011 + 3 C00001

Comment

three-step reaction (see R09583+R09584+R09585)

Reaction class

RC02295

C00078_C02937

Enzyme

1.14.14.156

Pathway

rn00380

Tryptophan metabolism

rn00966

Glucosinolate biosynthesis

rn01100

Metabolic pathways

rn01110

Biosynthesis of secondary metabolites

rn01210

2-Oxocarboxylic acid metabolism

Module

M00370

Glucosinolate biosynthesis, tryptophan => glucobrassicin

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
    1.14.14.156
     R08160  L-Tryptophan + 2 [Reduced NADPH---hemoprotein reductase] + 2 Oxygen <=> Indole-3-acetaldehyde oxime + 2 [Oxidized NADPH---hemoprotein reductase] + CO2 + 3 H2O

Orthology

K11812

tryptophan N-monooxygenase [EC:1.14.14.156]

K11813

tryptophan N-monooxygenase [EC:1.14.14.156]

Other DBs

RHEA:

33282

LinkDB

DBGET integrated database retrieval system