Information on EC 2.4.1.126 - hydroxycinnamate 4-beta-glucosyltransferase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.4.1.126
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RECOMMENDED NAME
GeneOntology No.
hydroxycinnamate 4-beta-glucosyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
UDP-glucose + trans-4-hydroxycinnamate = UDP + 4-O-beta-D-glucosyl-4-hydroxycinnamate
show the reaction diagram
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-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hexosyl group transfer
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-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
daphnetin modification
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esculetin modification
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SYSTEMATIC NAME
IUBMB Comments
UDP-glucose:trans-4-hydroxycinnamate 4-O-beta-D-glucosyltransferase
Acts on 4-coumarate, ferulate, caffeate and sinapate, forming a mixture of 4-glucosides and glucose esters (cf. EC 2.4.1.120 sinapate 1-glucosyltransferase).
CAS REGISTRY NUMBER
COMMENTARY hide
77848-85-2
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
var. cerasiforme
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-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
phenylpropanoid metabolism; phenylpropanoid metabolism; phenylpropanoid metabolism; phenylpropanoid metabolism
physiological function
specific role for UGT84A3 in the accumulation of cell wall-bound 4-coumarate
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
UDP-alpha-D-glucose + 4-hydroxycinnamate
UDP + 4-O-(beta-D-glucopyranosyl)-4-hydroxycinnamate
show the reaction diagram
UDP-alpha-D-glucose + sinapate
UDP + 4-O-(beta-D-glucopyranosyl)-4-hydroxycinnamate
show the reaction diagram
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-
-
-
-
?
UDP-alpha-D-glucose + sinapic acid
UDP + 4-O-beta-D-glucosyl-sinapic acid + 1-O-sinapoyl-beta-D-glucose
show the reaction diagram
-
-
a mixture of the glucoside and the glucose ester is formed
?
UDPglucose + aesculin
UDP + 4-O-beta-D-glucosyl-aesculin
show the reaction diagram
-
-
-
-
?
UDPglucose + caffeic acid
UDP + 4-O-glucosyl-caffeic acid
show the reaction diagram
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-
no glucose ester is formed
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UDPglucose + daphnetin
UDP + 4-O-beta-D-glucosyl-daphnetin
show the reaction diagram
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-
-
-
?
UDPglucose + ferulic acid
UDP + feruloyl-beta-D-glucose + 4-O-glucosyl-ferulic acid
show the reaction diagram
-
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a mixture of the glucoside and the glucose ester is formed
?
UDPglucose + kaempferol
UDP + 4-O-beta-D-glucosyl-kaempferol
show the reaction diagram
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-
-
-
?
UDPglucose + p-coumaric acid
UDP + p-coumaroyl-beta-D-glucose + 4-O-glucosyl-p-coumaric acid
show the reaction diagram
-
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a mixture of the glucoside and the glucose ester is formed
?
UDPglucose + quercetin
UDP + 4-O-beta-D-glucosyl-quercetin
show the reaction diagram
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-
-
-
?
UDPglucose + scopoletin
UDP + 4-O-beta-D-glucosyl-scopoletin
show the reaction diagram
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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
UDP-alpha-D-glucose + 4-hydroxycinnamate
UDP + 4-O-(beta-D-glucopyranosyl)-4-hydroxycinnamate
show the reaction diagram
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
MnCl2
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0.006-0.01 mM: stimulation of about 10%
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Ca2+
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0.1-10 mM: 20-50% inhibition
EDTA
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0.001 mM: 30% inhibition, 0.01 mM: complete inactivation
iodoacetate
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0.001-0.01 mM: 50-70% inhibition
Mg2+
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0.1-10 mM: 20-50% inhibition
Mn2+
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0.1-10 mM: 20-80% inhibition
PCMB
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0.001-0.01 mM: 50-70% inhibition
UDP
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1 mM, 70% inhibition after 60 min
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0015
caffeic acid
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0.0014
ferulic acid
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0.0008
p-coumaric acid
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0.0025
Sinapic acid
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0.01
UDPglucose
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reaction with ferulic acid
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00112
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reaction with ferulic acid
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7
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formation of glucose ester of p-coumaric acid
8
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formation of glucoside of p-coumaric acid
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
beta-mercaptoethanol, 10 mM, stabilizes, 80% restorage of activity by its addition after treatment with p-chloromercuribenzoate
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, purified enzyme, complete loss of activity after 12-24 h
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0-4°C, purified enzyme, 40% loss of activity after 24 h, 70% loss of activity after 48 h
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
binary plasmid constructs for transformation of Arabidopsis are introduced into Agrobacterium tumefaciens by electroporation, plants are transformed by the floral dip method, for selection of transgenic plants T1 seeds are surface-sterilized in 70% ethanol for 2 min followed by a mixture of Tween 20 and sodium hypochloride for 10 min, seeds are rinsed thoroughly with sterile water and after swelling over night at 4°C plated on modified MS medium supplemented with carbenicillin and kanamycin, after scoring the development of antibiotic damage symptoms for 14 days post treatment, kanamycin resistant plants are transferred; binary plasmid constructs for transformation of Arabidopsis are introduced into Agrobacterium tumefaciens by electroporation, plants are transformed by the floral dip method, for selection of transgenic plants T1 seeds are surface-sterilized in 70% ethanol for 2 min followed by a mixture of Tween 20 and sodium hypochloride for 10 min, seeds are rinsed thoroughly with sterile water and after swelling over night at 4°C plated on modified MS medium supplemented with carbenicillin and kanamycin, after scoring the development of antibiotic damage symptoms for 14 days post treatment, kanamycin resistant plants are transferred; binary plasmid constructs for transformation of Arabidopsis are introduced into Agrobacterium tumefaciens by electroporation, plants are transformed by the floral dip method, for selection of transgenic plants T1 seeds are surface-sterilized in 70% ethanol for 2 min followed by a mixture of Tween 20 and sodium hypochloride for 10 min, seeds are rinsed thoroughly with sterile water and after swelling over night at 4°C plated on modified MS medium supplemented with carbenicillin and kanamycin, after scoring the development of antibiotic damage symptoms for 14 days post treatment, kanamycin resistant plants are transferred; binary plasmid constructs for transformation of Arabidopsis are introduced into Agrobacterium tumefaciens by electroporation, plants are transformed by the floral dip method, for selection of transgenic plants T1 seeds are surface-sterilized in 70% ethanol for 2 min followed by a mixture of Tween 20 and sodium hypochloride for 10 min, seeds are rinsed thoroughly with sterile water and after swelling over night at 4°C plated on modified MS medium supplemented with carbenicillin and kanamycin, after scoring the development of antibiotic damage symptoms for 14 days post treatment, kanamycin resistant plants are transferred
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
exposure of plants to enhanced UV-B radiation induced the UGT84A-encoding genes and leads to a transient increase in sinapoylglucose and sinapoylmalate concentrations, compared to the wild type, crude protein extracts from leaves of UGT84A1 overexpression plants displayed increased activity toward 4-coumarate and ferulate, the preferred in vitro substrates, the overexpressing line UGT84A1 exhibits increased levels of sinapoylglucose in seeds and seedlings, the seed sinapine content is slightly increased in UGT84A1, overexpression of UGT84A1 results in a significant increase of cell wall-bound sinapate; exposure of plants to enhanced UV-B radiation induced the UGT84A-encoding genes and leads to a transient increase in sinapoylglucose and sinapoylmalate concentrations, leaves of UGT84A3 overexpression displayed a significantly higher capacity to synthesize feruloylglucose, the overexpressing line UGT84A3 exhibits increased levels of sinapoylglucose in seeds and seedlings, the seed sinapine content is slightly increased in UGT84A3, analysis of liberated from cell walls reveals for UGT84A3 a significant increase in cell wall-associated 4-coumarate, ferulate and sinapate; exposure of plants to enhanced UV-B radiation induced the UGT84A-encoding genes and leads to a transient increase in sinapoylglucose and sinapoylmalate concentrations, overexpression plants did not display changes in UGT specificity of leave extracts, the overexpressing line UGT84A4 exhibits increased levels of sinapoylglucose in seeds and seedlings, the seed sinapine content is slightly increased; exposure of plants to enhanced UV-B radiation induced the UGT84A-encoding genes and leads to a transient increase in sinapoylglucose and sinapoylmalate concentrations, UGT84A2 overexpression caused increasing activity toward sinapate, the overexpressing line UGT84A2 exhibits increased levels of sinapoylglucose in seeds and seedlings, the seed sinapine content is slightly increased in UGT84A2, mature leaves of UGT84A2 show a slight increase in the sinapoylmalate content, overexpression of UGT84A2 results in a significant increase of cell wall-bound sinapate
given the impact of UGT84A3 overexpression on the amount of cell wall-associated hydroxycinnamates, analysis of the cell wall fraction of the insertion knock-out mutant UGT84A3 shows a significant decrease of the 4-coumarate content in cell walls of null mutant whereas the levels of ferulate and sinapate are not changed compared to the wild type