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

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EC NUMBER
COMMENTARY hide
1.14.13.36
-
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RECOMMENDED NAME
GeneOntology No.
5-O-(4-coumaroyl)-D-quinate 3'-monooxygenase
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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
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
-
chlorogenic acid biosynthesis I
-
-
chlorogenic acid biosynthesis II
-
-
Flavonoid biosynthesis
-
-
Metabolic pathways
-
-
phaselate biosynthesis
-
-
phenylpropanoid biosynthesis
-
-
Phenylpropanoid biosynthesis
-
-
Stilbenoid, diarylheptanoid and gingerol biosynthesis
-
-
phenylpropanoid biosynthesis
-
-
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.
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CAS REGISTRY NUMBER
COMMENTARY hide
112131-08-5
-
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
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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
-
?
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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
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
-
strictly specific
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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
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
diethyldithiocarbonate
-
2fold activation at 0.2-2 mM
KCN
-
2fold activation at 1-10 mM
light exposure
-
4fold activation after 20 h irradiation at 350 nm
-
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.3
-
half-maximal activity
395989
8.6
-
half-maximal activity
395989
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
-
half-life: 10 min
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-70�C, stable for several months
-
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.13.36)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
SYSTERS
Protein Mutant Database
InterPro (database of protein families, domains and functional sites)