KEGG   ORTHOLOGY: K09754
Entry
K09754                      KO                                     

Name
CYP98A, C3'H
Definition
5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase [EC:1.14.14.96]
Pathway
ko00940  Phenylpropanoid biosynthesis
ko00941  Flavonoid biosynthesis
ko00945  Stilbenoid, diarylheptanoid and gingerol biosynthesis
ko01100  Metabolic pathways
ko01110  Biosynthesis of secondary metabolites
Module
M00039  Monolignol biosynthesis, phenylalanine/tyrosine => monolignol
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00940 Phenylpropanoid biosynthesis
    K09754  CYP98A, C3'H; 5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase
   00945 Stilbenoid, diarylheptanoid and gingerol biosynthesis
    K09754  CYP98A, C3'H; 5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase
   00941 Flavonoid biosynthesis
    K09754  CYP98A, C3'H; 5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase
 09180 Brite Hierarchies
  09181 Protein families: metabolism
   00199 Cytochrome P450
    K09754  CYP98A, C3'H; 5-O-(4-coumaroyl)-D-quinate 3'-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
    1.14.14.96  5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase
     K09754  CYP98A, C3'H; 5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase
Cytochrome P450 [BR:ko00199]
 Cytochrome P450, plant type
  CYP98 family
   K09754  CYP98A, C3'H; 5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase
Other DBs
RN: R04342 R06582
GO: 0047083
Genes
ATH: AT2G40890(CYP98A3)
ALY: 9315964
CRB: 17887658
CSAT: 104782574 104785308 104792955
EUS: EUTSA_v10016538mg
BRP: 103857960 103865848 103866522
BNA: 106352767 106386334 106391625 106395719 106431114 106438010 106454525
BOE: 106335822 106340718 106342398
RSZ: 108847330 108848401 108857959 108858042 108860679
THJ: 104803227
CPAP: 110811301
CIT: 102624231
TCC: 18598608
DZI: 111293639
GMX: 100811080 606506(CYP98A2)
VRA: 106753926
VAR: 108346061
VUN: 114186352
CCAJ: 109802555
CAM: 101502624
LJA: Lj1g3v4081860.1(Lj1g3v4081860.1)
ADU: 107494128
AIP: 107604697
LANG: 109326958
FVE: 101310387
RCN: 112191575
ZJU: 107431535
CSV: 101217257
CMO: 103486874
CMAX: 111482281
CMOS: 111441713
CPEP: 111790179
JCU: 105636120
HBR: 110668477
MESC: 110621178
VVI: 100263633
INI: 109159148
NNU: 104588272
OSA: 4339188
DOSA: Os05t0494000-01(Os05g0494000)
OBR: 102712257
BDI: 100835531
ATS: 109731922(LOC109731922) 109752053(LOC109752053) 109757203(LOC109757203) 109771149(LOC109771149) 109775586(LOC109775586)
SITA: 101771055
MUS: 103995155
DCT: 110101632
PEQ: 110024997
AOF: 109819911
SMO: SELMODRAFT_450942(C3'H1-1) SELMODRAFT_450943(C3'H1-2)
PPP: 112275074
AG: AAL99200(CYP98A13v1) AAL99201(CYP98A13v2) CAE47490(CYP98A11)
 » show all
Reference
PMID:9484480 (CYP98A1)
  Authors
Bak S, Kahn RA, Nielsen HL, Moller BL, Halkier BA
  Title
Cloning of three A-type cytochromes P450, CYP71E1, CYP98, and CYP99 from Sorghum bicolor (L.) Moench by a PCR approach and identification by expression in Escherichia coli of CYP71E1 as a multifunctional cytochrome P450 in the biosynthesis of the cyanogenic glucoside dhurrin.
  Journal
Plant Mol Biol 36:393-405 (1998)
DOI:10.1023/A:1005915507497
  Sequence
[sbi:8077042]
Reference
PMID:17160453 (CYP98A11)
  Authors
Morant M, Schoch GA, Ullmann P, Ertunc T, Little D, Olsen CE, Petersen M, Negrel J, Werck-Reichhart D
  Title
Catalytic activity, duplication and evolution of the CYP98 cytochrome P450 family in wheat.
  Journal
Plant Mol Biol 63:1-19 (2007)
DOI:10.1007/s11103-006-9028-8
  Sequence
Reference
PMID:12428018 (CYP98A13)
  Authors
Gang DR, Beuerle T, Ullmann P, Werck-Reichhart D, Pichersky E
  Title
Differential production of meta hydroxylated phenylpropanoids in sweet basil peltate glandular trichomes and leaves is controlled by the activities of specific acyltransferases and hydroxylases.
  Journal
Plant Physiol 130:1536-44 (2002)
DOI:10.1104/pp.007146
  Sequence
Reference
  Authors
Costa MA, Collins RE, Anterola AM, Cochrane FC, Davin LB, Lewis NG.
  Title
An in silico assessment of gene function and organization of the phenylpropanoid pathway metabolic networks in Arabidopsis thaliana and limitations thereof.
  Journal
Phytochemistry 64:1097-112 (2003)
DOI:10.1016/S0031-9422(03)00517-X

KEGG   ENZYME: 1.14.14.96
Entry
EC 1.14.14.96               Enzyme                                 

Name
5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase;
5-O-(4-coumaroyl)-D-quinate/shikimate 3'-hydroxylase;
coumaroylquinate(coumaroylshikimate) 3'-monooxygenase;
CYP98A3 (gene name)
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
trans-5-O-(4-coumaroyl)-D-quinate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)
Reaction(IUBMB)
trans-5-O-(4-coumaroyl)-D-quinate + [reduced NADPH---hemoprotein reductase] + O2 = trans-5-O-caffeoyl-D-quinate + [oxidized NADPH---hemoprotein reductase] + H2O [RN:R04342]
Reaction(KEGG)
R04342;
(other) R06582
Substrate
trans-5-O-(4-coumaroyl)-D-quinate [CPD:C12208];
[reduced NADPH---hemoprotein reductase] [CPD:C03024];
O2 [CPD:C00007]
Product
trans-5-O-caffeoyl-D-quinate [CPD:C00852];
[oxidized NADPH---hemoprotein reductase] [CPD:C03161];
H2O [CPD:C00001]
Comment
A cytochrome P-450 (heme-thiolate) protein, found in plants. It also acts on trans-5-O-(4-coumaroyl)shikimate.
History
EC 1.14.14.96 created 1990 as EC 1.14.13.36, transferred 2018 to EC 1.14.14.96
Pathway
ec00940  Phenylpropanoid biosynthesis
ec00941  Flavonoid biosynthesis
ec00945  Stilbenoid, diarylheptanoid and gingerol biosynthesis
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K09754  5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase
Genes
ATH: AT2G40890(CYP98A3)
ALY: 9315964
CRB: 17887658
CSAT: 104782574 104785308 104792955
EUS: EUTSA_v10016538mg
BRP: 103857960 103865848 103866522
BNA: 106352767 106386334 106391625 106395719 106431114 106438010 106454525
BOE: 106335822 106340718 106342398
RSZ: 108847330 108848401 108857959 108858042 108860679
THJ: 104803227
CPAP: 110811301
CIT: 102624231
TCC: 18598608
DZI: 111293639
GMX: 100811080 606506(CYP98A2)
VRA: 106753926
VAR: 108346061
VUN: 114186352
CCAJ: 109802555
CAM: 101502624
LJA: Lj1g3v4081860.1(Lj1g3v4081860.1)
ADU: 107494128
AIP: 107604697
LANG: 109326958
FVE: 101310387
RCN: 112191575
ZJU: 107431535
CSV: 101217257
CMO: 103486874
CMAX: 111482281
CMOS: 111441713
CPEP: 111790179
JCU: 105636120
HBR: 110668477
MESC: 110621178
VVI: 100263633
INI: 109159148
NNU: 104588272
OSA: 4339188
DOSA: Os05t0494000-01(Os05g0494000)
OBR: 102712257
BDI: 100835531
ATS: 109731922(LOC109731922) 109752053(LOC109752053) 109757203(LOC109757203) 109771149(LOC109771149) 109775586(LOC109775586)
SITA: 101771055
MUS: 103995155
DCT: 110101632
PEQ: 110024997
AOF: 109819911
SMO: SELMODRAFT_450942(C3'H1-1) SELMODRAFT_450943(C3'H1-2)
PPP: 112275074
 » show all
Reference
1  [PMID:2821918]
  Authors
Kuhnl T, Koch U, Heller W, Wellmann E.
  Title
Chlorogenic acid biosynthesis: characterization of a light-induced microsomal 5-O-(4-coumaroyl)-D-quinate/shikimate 3'-hydroxylase from carrot (Daucus carota L.) cell suspension cultures.
  Journal
Arch Biochem Biophys 258:226-32 (1987)
DOI:10.1016/0003-9861(87)90339-0
Reference
2  [PMID:11429408]
  Authors
Schoch G, Goepfert S, Morant M, Hehn A, Meyer D, Ullmann P, Werck-Reichhart D
  Title
CYP98A3 from Arabidopsis thaliana is a 3'-hydroxylase of phenolic esters, a missing link in the phenylpropanoid pathway.
  Journal
J Biol Chem 276:36566-74 (2001)
DOI:10.1074/jbc.M104047200
  Sequence
[ath:AT2G40890]
Reference
3  [PMID:11967091]
  Authors
Franke R, Humphreys JM, Hemm MR, Denault JW, Ruegger MO, Cusumano JC, Chapple C
  Title
The Arabidopsis REF8 gene encodes the 3-hydroxylase of phenylpropanoid metabolism.
  Journal
Plant J 30:33-45 (2002)
DOI:10.1046/j.1365-313X.2002.01266.x
  Sequence
[ath:AT2G40890]
Reference
4  [PMID:19779199]
  Authors
Matsuno M, Compagnon V, Schoch GA, Schmitt M, Debayle D, Bassard JE, Pollet B, Hehn A, Heintz D, Ullmann P, Lapierre C, Bernier F, Ehlting J, Werck-Reichhart D
  Title
Evolution of a novel phenolic pathway for pollen development.
  Journal
Science 325:1688-92 (2009)
DOI:10.1126/science.1174095
  Sequence
[ath:AT2G40890]
Other DBs
ExplorEnz - The Enzyme Database: 1.14.14.96
IUBMB Enzyme Nomenclature: 1.14.14.96
ExPASy - ENZYME nomenclature database: 1.14.14.96
BRENDA, the Enzyme Database: 1.14.14.96
CAS: 112131-08-5

KEGG   REACTION: R06582
Entry
R06582                      Reaction                               

Name
trans-5-O-(4-coumaroyl)-D-shikimate,[reduced NADPH---hemoprotein reductase]:oxygen oxidoreductase (3'-hydroxylating)
Definition
4-Coumaroylshikimate + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> 5-O-Caffeoylshikimic acid + [Oxidized NADPH---hemoprotein reductase] + H2O
Equation
Reaction class
RC00046  C02947_C10434
Enzyme
Pathway
rn00940  Phenylpropanoid biosynthesis
rn00941  Flavonoid biosynthesis
rn00945  Stilbenoid, diarylheptanoid and gingerol biosynthesis
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00039  Monolignol biosynthesis, phenylalanine/tyrosine => monolignol
Orthology
K09754  5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase [EC:1.14.14.96]

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