Information on EC 1.14.13.36 - 5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase

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The expected taxonomic range for this enzyme is: Daucus carota

EC NUMBER
COMMENTARY hide
1.14.13.36
-
RECOMMENDED NAME
GeneOntology No.
5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
trans-5-O-(4-coumaroyl)-D-quinate + NADPH + H+ + O2 = trans-5-O-caffeoyl-D-quinate + NADP+ + H2O
show the reaction diagram
Also acts on trans-5-O-(4-coumaroyl)shikimate
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
-
chlorogenic acid biosynthesis I
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-
chlorogenic acid biosynthesis II
-
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Flavonoid biosynthesis
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Metabolic pathways
-
-
phaselate biosynthesis
-
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phenylpropanoid biosynthesis
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Phenylpropanoid biosynthesis
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Stilbenoid, diarylheptanoid and gingerol biosynthesis
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phenylpropanoid biosynthesis
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suberin monomers biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
trans-5-O-(4-coumaroyl)-D-quinate,NADPH:oxygen oxidoreductase (3'-hydroxylating)
Also acts on trans-5-O-(4-coumaroyl)shikimate.
CAS REGISTRY NUMBER
COMMENTARY hide
112131-08-5
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
trans-5-O-(4-coumaroyl)-D-quinate + NADPH + O2
trans-5-O-caffeoyl-D-quinate + NADP+ + H2O
show the reaction diagram
-
specific for the trans isomer, final step in the chlorogenic acid pathway, reaction is greatly enhanced by irradiation with blue/uv light
-
?
trans-5-O-(4-coumaroyl)shikimate + NADPH + O2
trans-5-O-caffeoylshikimate + NADP+ + H2O
show the reaction diagram
-
70% of the activity compared to trans-5-O-(4-coumaroyl)-D-quinate, specific for the trans isomer
-
?
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
trans-5-O-(4-coumaroyl)-D-quinate + NADPH + O2
trans-5-O-caffeoyl-D-quinate + NADP+ + H2O
show the reaction diagram
-
specific for the trans isomer, final step in the chlorogenic acid pathway, reaction is greatly enhanced by irradiation with blue/uv light
-
?
trans-5-O-(4-coumaroyl)shikimate + NADPH + O2
trans-5-O-caffeoylshikimate + NADP+ + H2O
show the reaction diagram
-
70% of the activity compared to trans-5-O-(4-coumaroyl)-D-quinate, specific for the trans isomer
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
-
strictly specific
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome c
-
76% inhibition at 0.1 mM
diethyldicarbonate
-
31% inhibition at 2 mM
p-chloromercuribenzoate
-
32% inhibition at 0.5 mM
Tetcyclacis
-
38% inhibition at 0.01 mM
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
diethyldithiocarbonate
-
2fold activation at 0.2-2 mM
KCN
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2fold activation at 1-10 mM
light exposure
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4fold activation after 20 h irradiation at 350 nm
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.3
-
half-maximal activity
395989
8.6
-
half-maximal activity
395989
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
-
half-life: 10 min
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-70°C, stable for several months
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