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

for references in articles please use BRENDA:EC1.14.13.36
Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Select one or more organisms in this record:


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
chlorogenic acid biosynthesis I
-
-
chlorogenic acid biosynthesis II
-
-
phaselate biosynthesis
-
-
phenylpropanoid biosynthesis
suberin monomers biosynthesis
-
-
Phenylpropanoid biosynthesis
-
-
Flavonoid biosynthesis
-
-
Stilbenoid, diarylheptanoid and gingerol biosynthesis
-
-
Metabolic pathways
-
-
Biosynthesis of secondary metabolites
-
-
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
Eucalyptus urophylla × Eucalyptus grandis
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
Eucalyptus urophylla × Eucalyptus grandis
-
Eucalyptus trees with down-regulated p-coumaroyl quinate/shikimate 3'-hydroxylase expression display lowered overall lignin content
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
-
2fold activation at 1-10 mM
light exposure
-
4fold activation after 20 h irradiation at 350 nm
-
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
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
biofuel production
Eucalyptus urophylla × Eucalyptus grandis
-
lignocellulosic materials provide an attractive replacement for food-based crops used to produce ethanol. Understanding the interactions within the cell wall is vital to overcome the highly recalcitrant nature of biomass. One factor imparting plant cell wall recalcitrance is lignin, which can be manipulated by making changes in the lignin biosynthetic pathway. Eucalyptus trees with down-regulated cinnamate 4-hydroxylase (C4H) or p-coumaroyl quinate/shikimate 3'-hydroxylase (C3'H) expression display lowered overall lignin content. Lowering lignin content rather than altering sinapyl alcohol/coniferyl alcohol/4-coumaryl alcohol ratios is found to have the largest impact on reducing recalcitrance of the transgenic eucalyptus variants. The development of lower recalcitrance trees opens up the possibility of using alternative pretreatment strategies in biomass conversion processes that can reduce processing costs