Information on EC 2.4.1.120 - sinapate 1-glucosyltransferase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.4.1.120
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RECOMMENDED NAME
GeneOntology No.
sinapate 1-glucosyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
UDP-alpha-glucose + sinapate = UDP + 1-O-sinapoyl-beta-D-glucose
show the reaction diagram
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
Phenylpropanoid biosynthesis
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-
sinapate ester biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
UDP-glucose:sinapate D-glucosyltransferase
Some other hydroxycinnamates, including 4-coumarate, ferulate and caffeate, can act as acceptors, but more slowly. Only glucose esters, not glucosides, are formed (cf. EC 2.4.1.126 hydroxycinnamate 4-beta-glucosyltransferase).
CAS REGISTRY NUMBER
COMMENTARY hide
74082-53-4
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
dTDP-alpha-D-glucose + sinapic acid
dTDP + 1-O-sinapoyl-beta-D-glucose
show the reaction diagram
UDP-alpha-D-glucose + 3,5-dihydroxybenzoic acid
UDP + 1-O-(3,5-dihydroxybenzoyl)-beta-D-glucose
show the reaction diagram
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5% of activity compared to sinapic acid
-
-
?
UDP-alpha-D-glucose + 4-coumarate
UDP + 1-O-(4-coumaroyl)-beta-D-glucose
show the reaction diagram
UDP-alpha-D-glucose + 4-coumaric acid
UDP + 1-O-(4-coumaroyl)-beta-D-glucose
show the reaction diagram
UDP-alpha-D-glucose + 4-hydroxybenzoic acid
UDP + 1-O-(4-hydroxybenzoyl)-beta-D-glucose
show the reaction diagram
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31% of activity compared to sinapic acid
-
-
?
UDP-alpha-D-glucose + 5-hydroxyferulic acid
UDP + 1 O-(5-hydroxyferuloyl)-beta-D-glucose
show the reaction diagram
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39% of the activity with sinapic acid
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-
?
UDP-alpha-D-glucose + anthranilic acid
UDP + 1-O-anthraniloyl-beta-D-glucose
show the reaction diagram
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31% of activity compared to sinapic acid
-
-
?
UDP-alpha-D-glucose + benzoic acid
UDP + 1-O-benzoyl-beta-D-glucose
show the reaction diagram
-
39% of activity compared to sinapic acid
-
-
?
UDP-alpha-D-glucose + caffeic acid
UDP + 1-O-caffeoyl-beta-D-glucose
show the reaction diagram
UDP-alpha-D-glucose + cinnamate
UDP + 1-O-cinnamoyl-beta-D-glucose
show the reaction diagram
20% activity compared to sinapate
-
-
?
UDP-alpha-D-glucose + cinnamic acid
UDP + 1-O-cinnamoyl-beta-D-glucose
show the reaction diagram
UDP-alpha-D-glucose + ferulate
UDP + 1-O-feruloyl-beta-D-glucose
show the reaction diagram
UDP-alpha-D-glucose + sinapate
UDP + 1-O-sinapoyl-beta-D-glucose
show the reaction diagram
UDP-alpha-D-glucose + sinapic acid
UDP + 1-O-sinapoyl-beta-D-glucose
show the reaction diagram
UDP-alpha-D-glucose + syringic acid
UDP + 1-O-syringoyl-beta-D-glucose
show the reaction diagram
UDP-alpha-D-glucose + vanillic acid
UDP + 1-O-vanilloyl-beta-D-glucose
show the reaction diagram
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36% of activity compared to sinapic acid
-
-
?
UDP-glucose + caffeate
UDP + 1-caffeoyl-D-glucose
show the reaction diagram
UDP-glucose + sinapate
UDP + 1-O-(E)-sinapoyl-beta-D-glucose
show the reaction diagram
-
-
-
-
?
UDPalpha-D-glucose + ferulic acid
UDP + 1-O-feruloyl-beta-D-glucose
show the reaction diagram
additional information
?
-
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 + sinapate
UDP + 1-O-sinapoyl-beta-D-glucose
show the reaction diagram
UDP-alpha-D-glucose + sinapic acid
UDP + 1-O-sinapoyl-beta-D-glucose
show the reaction diagram
additional information
?
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the hyper-fluorescent trichome phenotype of the brt1 mutant of Arabidopsis is the result of a defect in a sinapic acid:UDPG glucosyltransferase
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mg2+
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modest stimulation
Mn2+
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modest stimulation
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
p-hydroxymercuribenzoate
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-
PCMB
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100% inhibition at 1 mM, activity can be restored up to 50% by addition of 10 mM dithiothreitol, 24% inhibition at 0.1 mM, activity can be completely restored by 10 mM dithiothreitol
UDPmannose
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weak inhibition
UDPxylose
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weak inhibition
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-mercaptoethanol
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stimulation
dithiothreitol
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10 mM, 3fold stimulation
additional information
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SH-group required
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3.6
4-coumarate
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2.3
caffeate
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1.7
ferulate
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0.72
sinapate
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0.03 - 0.16
Sinapic acid
1
UDP-glucose
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0.055 - 2.4
UDPglucose
additional information
additional information
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0094
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reaction with sinapic acid
0.018
recombinant enzyme, substrate sinapate
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.8
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potassium phosphate buffer
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.5 - 8.5
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no activity detected below pH 4.5 and above pH 8.5
5 - 7
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pH 5.0: 85% of maximal activity, pH 7.0: 63% of maximal activity
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25 - 45
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25°C: 50% of maximal activity, 45°C: 80% of maximal activity
32 - 50
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32°C: maximal activity, 50°C: no activity above
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.1
sequence calculation
6.6
sequence calculation, mature protein
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
42000
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gel filtration
50270
x * 55970, unmodified enzyme, amino acid sequence calculation, x * 50270, mature enzyme, amino acid sequence calculation
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycoprotein
enzyme is putatively N-glycosylated in the Golgi apparatus
proteolytic modification
enzyme contains a signal peptide, cleavage probably after residue D19
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4
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2 d, less than 10% loss of activity
25
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24 h more than 90% loss of activity
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, litte loss of activity after 1 month
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4°C, 8 days, 23% loss of activity
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4°C, less than 10% loss of activity after 2 d, more than 90% loss of activity after 1 month
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enzyme is less stable at -20°C than at 4°C
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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
construction of a cDNA library, DNA and amino acid sequence determination and analysis, functional expression in Escherichia coli strain M15 as soluble protein
gene UGT84A9, semi-quantitative RT-PCR, enzyme expression analysis
genomic organization analysis, expression of C-terminally His-tagged enzyme in Escherichia coli strain BL21(DE3)
heterologous expression in Escherichia coli strain BL21; heterologous expression in Escherichia coli strain BL21; heterologous expression in Escherichia coli strain BL21; heterologous expression in Escherichia coli strain BL21; heterologous expression in Escherichia coli strain BL21
stilbene synthase gene isolated from Vitis vinifera L. is cloned under control of the seed-specific napin promotor and introduced into Brassica napus L. by Agrobacterium-mediated co-transformation together with a ds-RNA-interference construct deduced from the sequence of UDP-glucose:sinapate glucosyltransferase (BnSGT1)
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
Brassicus napus harbors 2 distinguishable sequence types of the UGT84A9 gene designated as UGT84A9-1 and UGT84A9-2, UGT84A9-1 is the predominantly expressed variant, which is significantly up-regulated during the seed filling phase, when sinapate ester biosynthesis exhibits strongest activity; Brassicus napus harbors 2 distinguishable sequence types of the UGT84A9 gene designated as UGT84A9-1 and UGT84A9-2, UGT84A9-1 is the predominantly expressed variant, which is significantly up-regulated during the seed filling phase, when sinapate ester biosynthesis exhibits strongest activity; Brassicus napus harbors 2 distinguishable sequence types of the UGT84A9 gene designated as UGT84A9-1 and UGT84A9-2, UGT84A9-1 is the predominantly expressed variant, which is significantly up-regulated during the seed filling phase, when sinapate ester biosynthesis exhibits strongest activity; Brassicus napus harbors 2 distinguishable sequence types of the UGT84A9 gene designated as UGT84A9-1 and UGT84A9-2, UGT84A9-1 is the predominantly expressed variant, which is significantly up-regulated during the seed filling phase, when sinapate ester biosynthesis exhibits strongest activity; Brassicus napus harbors 2 distinguishable sequence types of the UGT84A9 gene designated as UGT84A9-1 and UGT84A9-2, UGT84A9-1 is the predominantly expressed variant, which is significantly up-regulated during the seed filling phase, when sinapate ester biosynthesis exhibits strongest activity
the genomic microstructures reveal the presence of several transposon-derived sequence elements at all 4 UGT84A9 loci which underlie increased reorganization, weakly expressed sequence type 2 orthologs UGT84A9c and d in the Brassica genomes might indicate that these gene copies are necessary for genetic robustness; the genomic microstructures reveal the presence of several transposon-derived sequence elements at all 4 UGT84A9 loci which underlie increased reorganization, weakly expressed sequence type 2 orthologs UGT84A9c and d in the Brassica genomes might indicate that these gene copies are necessary for genetic robustness; the genomic microstructures reveal the presence of several transposon-derived sequence elements at all 4 UGT84A9 loci which underlie increased reorganization, weakly expressed sequence type 2 orthologs UGT84A9c and d in the Brassica genomes might indicate that these gene copies are necessary for genetic robustness; the genomic microstructures reveal the presence of several transposon-derived sequence elements at all 4 UGT84A9 loci which underlie increased reorganization, weakly expressed sequence type 2 orthologs UGT84A9c and d in the Brassica genomes might indicate that these gene copies are necessary for genetic robustness; the genomic microstructures reveal the presence of several transposon-derived sequence elements at all 4 UGT84A9 loci which underlie increased reorganization, weakly expressed sequence type 2 orthologs UGT84A9c and d in the Brassica genomes might indicate that these gene copies are necessary for genetic robustness
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
agriculture
the genes encoding this enzyme are considered as potential targets for molecular breeding of low sinapine oilseed rape; the genes encoding this enzyme are considered as potential targets for molecular breeding of low sinapine oilseed rape; the genes encoding this enzyme are considered as potential targets for molecular breeding of low sinapine oilseed rape; the genes encoding this enzyme are considered as potential targets for molecular breeding of low sinapine oilseed rape; the genes encoding this enzyme are considered as potential targets for molecular breeding of low sinapine oilseed rape