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dTDP-alpha-D-glucose + sinapic acid
dTDP + 1-O-sinapoyl-beta-D-glucose
UDP-alpha-D-glucose + 3,5-dihydroxybenzoic acid
UDP + 1-O-(3,5-dihydroxybenzoyl)-beta-D-glucose
-
5% of activity compared to sinapic acid
-
-
?
UDP-alpha-D-glucose + 4-coumarate
UDP + 1-O-(4-coumaroyl)-beta-D-glucose
UDP-alpha-D-glucose + 4-coumaric acid
UDP + 1-O-(4-coumaroyl)-beta-D-glucose
UDP-alpha-D-glucose + 4-hydroxybenzoic acid
UDP + 1-O-(4-hydroxybenzoyl)-beta-D-glucose
-
31% of activity compared to sinapic acid
-
-
?
UDP-alpha-D-glucose + 5-hydroxyferulic acid
UDP + 1 O-(5-hydroxyferuloyl)-beta-D-glucose
-
39% of the activity with sinapic acid
-
-
?
UDP-alpha-D-glucose + anthranilic acid
UDP + 1-O-anthraniloyl-beta-D-glucose
-
31% of activity compared to sinapic acid
-
-
?
UDP-alpha-D-glucose + benzoic acid
UDP + 1-O-benzoyl-beta-D-glucose
-
39% of activity compared to sinapic acid
-
-
?
UDP-alpha-D-glucose + caffeic acid
UDP + 1-O-caffeoyl-beta-D-glucose
UDP-alpha-D-glucose + cinnamate
UDP + 1-O-cinnamoyl-beta-D-glucose
20% activity compared to sinapate
-
-
?
UDP-alpha-D-glucose + cinnamic acid
UDP + 1-O-cinnamoyl-beta-D-glucose
UDP-alpha-D-glucose + ferulate
UDP + 1-O-feruloyl-beta-D-glucose
UDP-alpha-D-glucose + sinapate
UDP + 1-O-sinapoyl-beta-D-glucose
UDP-alpha-D-glucose + sinapic acid
UDP + 1-O-sinapoyl-beta-D-glucose
UDP-alpha-D-glucose + syringic acid
UDP + 1-O-syringoyl-beta-D-glucose
UDP-alpha-D-glucose + vanillic acid
UDP + 1-O-vanilloyl-beta-D-glucose
-
36% of activity compared to sinapic acid
-
-
?
UDP-glucose + caffeate
UDP + 1-caffeoyl-D-glucose
UDP-glucose + sinapate
UDP + 1-O-(E)-sinapoyl-beta-D-glucose
-
-
-
-
?
UDPalpha-D-glucose + ferulic acid
UDP + 1-O-feruloyl-beta-D-glucose
additional information
?
-
dTDP-alpha-D-glucose + sinapic acid
dTDP + 1-O-sinapoyl-beta-D-glucose
-
96% of the activity with UDPglucose
-
-
r
dTDP-alpha-D-glucose + sinapic acid
dTDP + 1-O-sinapoyl-beta-D-glucose
-
-
-
-
?
UDP-alpha-D-glucose + 4-coumarate
UDP + 1-O-(4-coumaroyl)-beta-D-glucose
13% activity compared to sinapate
-
-
?
UDP-alpha-D-glucose + 4-coumarate
UDP + 1-O-(4-coumaroyl)-beta-D-glucose
recombinant enzyme, 2% efficiency compared to sinapate
-
-
?
UDP-alpha-D-glucose + 4-coumaric acid
UDP + 1-O-(4-coumaroyl)-beta-D-glucose
-
21% of the activity with sinapic acid
-
-
?
UDP-alpha-D-glucose + 4-coumaric acid
UDP + 1-O-(4-coumaroyl)-beta-D-glucose
-
40% of activity compared to sinapic acid
-
-
?
UDP-alpha-D-glucose + caffeic acid
UDP + 1-O-caffeoyl-beta-D-glucose
-
14% of the activity with sinapic acid
-
-
?
UDP-alpha-D-glucose + caffeic acid
UDP + 1-O-caffeoyl-beta-D-glucose
-
38% of activity compared to sinapic acid
-
-
?
UDP-alpha-D-glucose + cinnamic acid
UDP + 1-O-cinnamoyl-beta-D-glucose
-
24% of the activity with sinapic acid
-
-
?
UDP-alpha-D-glucose + cinnamic acid
UDP + 1-O-cinnamoyl-beta-D-glucose
-
16% of activity compared to sinapic acid
-
-
?
UDP-alpha-D-glucose + ferulate
UDP + 1-O-feruloyl-beta-D-glucose
17% activity compared to sinapate
-
-
?
UDP-alpha-D-glucose + ferulate
UDP + 1-O-feruloyl-beta-D-glucose
recombinant enzyme, 4% efficiency compared to sinapate
-
-
?
UDP-alpha-D-glucose + sinapate
UDP + 1-O-sinapoyl-beta-D-glucose
-
-
-
?
UDP-alpha-D-glucose + sinapate
UDP + 1-O-sinapoyl-beta-D-glucose
-
-
-
?
UDP-alpha-D-glucose + sinapate
UDP + 1-O-sinapoyl-beta-D-glucose
-
-
-
-
?
UDP-alpha-D-glucose + sinapate
UDP + 1-O-sinapoyl-beta-D-glucose
-
-
-
?
UDP-alpha-D-glucose + sinapate
UDP + 1-O-sinapoyl-beta-D-glucose
best substrate
-
-
?
UDP-alpha-D-glucose + sinapate
UDP + 1-O-sinapoyl-beta-D-glucose
-
one of the key enzymes in sinapate ester biosynthesis, sinapate ester content and pattern in seeds, overview
-
-
?
UDP-alpha-D-glucose + sinapate
UDP + 1-O-sinapoyl-beta-D-glucose
regulation of the sinapate ester metabolism, enzyme expression is restricted to developing seeds, where it is involved in accumulation kinetics of corresponding metabolites
-
-
?
UDP-alpha-D-glucose + sinapate
UDP + 1-O-sinapoyl-beta-D-glucose
recombinant enzyme, best substrate
-
-
?
UDP-alpha-D-glucose + sinapate
UDP + 1-O-sinapoyl-beta-D-glucose
-
-
-
?
UDP-alpha-D-glucose + sinapate
UDP + 1-O-sinapoyl-beta-D-glucose
-
-
-
-
?
UDP-alpha-D-glucose + sinapate
UDP + 1-O-sinapoyl-beta-D-glucose
-
-
-
-
?
UDP-alpha-D-glucose + sinapic acid
UDP + 1-O-sinapoyl-beta-D-glucose
-
-
-
r
UDP-alpha-D-glucose + sinapic acid
UDP + 1-O-sinapoyl-beta-D-glucose
-
-
-
r
UDP-alpha-D-glucose + sinapic acid
UDP + 1-O-sinapoyl-beta-D-glucose
-
-
-
r
UDP-alpha-D-glucose + sinapic acid
UDP + 1-O-sinapoyl-beta-D-glucose
-
-
-
r
UDP-alpha-D-glucose + sinapic acid
UDP + 1-O-sinapoyl-beta-D-glucose
-
detoxification of sinapic acid and activation of sinapic acid for the subsequent sinapoyltransferase reaction leading to sinapoylmalate
-
-
r
UDP-alpha-D-glucose + syringic acid
UDP + 1-O-syringoyl-beta-D-glucose
-
10% of the activity with sinapic acid
-
-
?
UDP-alpha-D-glucose + syringic acid
UDP + 1-O-syringoyl-beta-D-glucose
-
35% of activity compared to sinapic acid
-
-
?
UDP-glucose + caffeate
UDP + 1-caffeoyl-D-glucose
10% activity compared to sinapate
-
-
?
UDP-glucose + caffeate
UDP + 1-caffeoyl-D-glucose
recombinant enzyme, 1% efficiency compared to sinapate
-
-
?
UDPalpha-D-glucose + ferulic acid
UDP + 1-O-feruloyl-beta-D-glucose
-
77% of the activity with sinapid acid
-
-
?
UDPalpha-D-glucose + ferulic acid
UDP + 1-O-feruloyl-beta-D-glucose
-
38% of activity compared to sinapic acid
-
-
?
additional information
?
-
-
the hyper-fluorescent trichome phenotype of the brt1 mutant of Arabidopsis is the result of a defect in a sinapic acid:UDPG glucosyltransferase
-
-
?
additional information
?
-
recombinant enzyme shows a broad substrate specificity, indole-3-acetate, 4-hydroxybenzoate, and salicylate are no substrates
-
-
?
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UDP-alpha-D-glucose + sinapate
UDP + 1-O-sinapoyl-beta-D-glucose
UDP-alpha-D-glucose + sinapic acid
UDP + 1-O-sinapoyl-beta-D-glucose
additional information
?
-
-
the hyper-fluorescent trichome phenotype of the brt1 mutant of Arabidopsis is the result of a defect in a sinapic acid:UDPG glucosyltransferase
-
-
?
UDP-alpha-D-glucose + sinapate
UDP + 1-O-sinapoyl-beta-D-glucose
-
-
-
?
UDP-alpha-D-glucose + sinapate
UDP + 1-O-sinapoyl-beta-D-glucose
-
-
-
?
UDP-alpha-D-glucose + sinapate
UDP + 1-O-sinapoyl-beta-D-glucose
-
-
-
?
UDP-alpha-D-glucose + sinapate
UDP + 1-O-sinapoyl-beta-D-glucose
-
one of the key enzymes in sinapate ester biosynthesis, sinapate ester content and pattern in seeds, overview
-
-
?
UDP-alpha-D-glucose + sinapate
UDP + 1-O-sinapoyl-beta-D-glucose
regulation of the sinapate ester metabolism, enzyme expression is restricted to developing seeds, where it is involved in accumulation kinetics of corresponding metabolites
-
-
?
UDP-alpha-D-glucose + sinapate
UDP + 1-O-sinapoyl-beta-D-glucose
-
-
-
?
UDP-alpha-D-glucose + sinapate
UDP + 1-O-sinapoyl-beta-D-glucose
-
-
-
-
?
UDP-alpha-D-glucose + sinapate
UDP + 1-O-sinapoyl-beta-D-glucose
-
-
-
-
?
UDP-alpha-D-glucose + sinapic acid
UDP + 1-O-sinapoyl-beta-D-glucose
-
-
-
-
r
UDP-alpha-D-glucose + sinapic acid
UDP + 1-O-sinapoyl-beta-D-glucose
-
detoxification of sinapic acid and activation of sinapic acid for the subsequent sinapoyltransferase reaction leading to sinapoylmalate
-
-
r
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additional information
in-silico structural analysis and molecular docking. Three dimensional structure and binding mode of sinapate with SGT enzyme, overview
evolution
-
the enzyme belongs to the glycosyltransferase-B type superfamily
evolution
-
the enzyme belongs to the glycosyltransferase-B type superfamily
malfunction
-
silencing the gene of UDP-glucose:sinapate glucosyltransferase (UGT84A9) reduces the anti-nutritive properties of the seeds by lowering the content of the major seed component sinapine (sinapoylcholine) and various minor sinapate esters. Silencing of UGT84A9 gene expression disrupt the metabolic flow through sinapoylglucose and alters the amounts and nature of the phenylpropanoid endproducts
malfunction
suppression of the key biosynthetic enzyme UDP-glucose:sinapic acid glucosyltransferase (UGT84A9) inhibits the biosynthesis of sinapine (sinapoylcholine), the major phenolic component of seeds. Suppression of the major sink pathway of sinapic acid impacts the metabolome of developing seeds and seedlings in UGT84A9-suppressing (UGT84A9i) lines, massive alterations become evident in late stages of seed development affecting the accumulation levels of 58 secondary and 7 primary metabolites, e.g. decreased amounts of various hydroxycinnamic acid esters, and increased formation of sinapic and syringic acid glycosides, overview. Suppression of UGT84A9 under control of the seed-specific NAPINC promoter is maintained in cotyledons during the first two weeks of seedling development and associated with a reduced and delayed transformation of sinapine into sinapoylmalate
metabolism
-
in the 1-O-sinapoylglucose biosynthesis pathway, Sinapic acid and UDP-glucose act as potential substrates for the UDP-glucose: sinapic acid glucosyltransferase, which catalyzes the transfer of glucose moiety from UDP-glucose to the 1-O-position of sinapic acid
metabolism
-
in the 1-O-sinapoylglucose biosynthesis pathway, Sinapic acid and UDP-glucose act as potential substrates for the UDP-glucose: sinapic acid glucosyltransferase, which catalyzes the transfer of glucose moiety from UDP-glucose to the 1-O-position of sinapic acid
metabolism
SGT and SCT, encoding enzymes UDP-glucose: sinapate glucosyltransferase and sinapoylglucose: choline sinapoyltransferase, respectively, are involved in the final two steps of sinapine biosynthetic pathway. Comparison of the two enzymes, overview
physiological function
key enzyme for sinapate ester biosynthesis, the glucosyltransferase UGT84A9 catalyzes the formation of 1-O-sinapoyl-D-glucose, which feeds as acyl donor into a broad range of accumulating sinapate esters, including the major antinutritive seed component sinapoylcholine (sinapine)
physiological function
key enzyme for sinapate ester biosynthesis, the glucosyltransferase UGT84A9 catalyzes the formation of 1-O-sinapoyl-D-glucose, which feeds as acyl donor into a broad range of accumulating sinapate esters, including the major antinutritive seed component sinapoylcholine (sinapine)
physiological function
the enzyme is involved in glycosylation and beta-oxidation as metabolic detoxification strategies to bypass intracellular accumulation of sinapic acid. Feedback regulation of hydroxycinnamic acid biosynthesis
physiological function
-
UDP-glucose: sinapic acid glucosyltransferase (USAGT1) from Daucus carota may influence anthocyanin biosynthesis of purple carrot taproots, DcUSAGT1 may play important roles in the stability of anthocyanin accumulation
physiological function
-
UDP-glucose: sinapic acid glucosyltransferase (USAGT1) from Daucus carota may influence anthocyanin biosynthesis of purple carrot taproots, DcUSAGT1 may play important roles in the stability of anthocyanin accumulation
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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 DcUSAGT1, sequence comparisons, the expression levels of DcUSAGT1 gene in the purple carrot taproots may be higher than those in non-purple carrot taproots, quantitative real-time PCR expression analysis, recombinant expression of His-tagged DcUSAGT1 in Escherichia coli strain BL21(DE3)
gene SGT, recombinant expression of full-length enzyme in Brassica juncea via Agrobacterium tumefaciens mediated transformation
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
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)
-
gene DcUSAGT1, sequence comparisons, the expression levels of DcUSAGT1 gene in the purple carrot taproots may be higher than those in non-purple carrot taproots, quantitative real-time PCR expression analysis, recombinant expression of His-tagged DcUSAGT1 in Escherichia coli strain BL21(DE3)
-
gene DcUSAGT1, sequence comparisons, the expression levels of DcUSAGT1 gene in the purple carrot taproots may be higher than those in non-purple carrot taproots, quantitative real-time PCR expression analysis, recombinant expression of His-tagged DcUSAGT1 in Escherichia coli strain BL21(DE3)
-
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Mock, H.P.; Strack, D.
Energetics of the uridine 5'-diphosphoglucose:hydroxycinnamic acid acyl-glucosyltransferase reaction
Phytochemistry
32
575-579
1993
Raphanus sativus
-
brenda
Strack, D.
Enzymatic synthesis of 1-sinapoylglucose from free sinapic acid and UDP-glucose by a cell-free system from Raphanus saticus seedlings
Z. Naturforsch. C
35
204-208
1979
Raphanus sativus
-
brenda
Nurmann, G.; Strack, D.
Formation of 1-sinapoylglucose by UDP-glucose: sinapic acid glucosyltransferase from cotyledons of Raphanus sativus
Z. Pflanzenphysiol.
102
11-17
1981
Raphanus sativus
-
brenda
Wang, S.X.; Ellis, B.E.
Enzymology of UDP-glucose:sinapic acid glucosyltransferase from Brassica napus
Phytochemistry
49
307-318
1998
Brassica napus
-
brenda
Baumert, A.; Milkowski, C.; Schmidt, J.; Nimtz, M.; Wray, V.; Strack, D.
Formation of a complex pattern of sinapate esters in Brassica napus seeds, catalyzed by enzymes of a serine carboxypeptidase-like acyltransferase family?
Phytochemistry
66
1334-1345
2005
Brassica napus
brenda
Milkowski, C.; Baumert, A.; Schmidt, D.; Nehlin, L.; Strack, D.
Molecular regulation of sinapate ester metabolism in Brassica napus: expression of genes, properties of the encoded proteins and correlation of enzyme activities with metabolite accumulation
Plant J.
38
80-92
2004
Brassica napus (Q9FYU7), Brassica napus
brenda
Milkowski, C.; Baumert, A.; Strack, D.
Cloning and heterologous expression of a rape cDNA encoding UDP-glucose:sinapate glucosyltransferase
Planta
211
883-886
2000
Brassica napus (Q9FYU7)
brenda
Huesken, A.; Baumert, A.; Milkowski, C.; Becker, H.C.; Strack, D.; Moellers, C.
Resveratrol glucoside (Piceid) synthesis in seeds of transgenic oilseed rape (Brassica napus L.)
Theor. Appl. Genet.
111
1553-1562
2005
Brassica napus
brenda
Sinlapadech, T.; Stout, J.; Ruegger, M.O.; Deak, M.; Chapple, C.
The hyper-fluorescent trichome phenotype of the brt1 mutant of Arabidopsis is the result of a defect in a sinapic acid:UDPG glucosyltransferase
Plant J.
49
655-668
2007
Arabidopsis thaliana
brenda
Meissner, D.; Albert, A.; Boettcher, C.; Strack, D.; Milkowski, C.
The role of UDP-glucose:hydroxycinnamate glucosyltransferases in phenylpropanoid metabolism and the response to UV-B radiation in Arabidopsis thaliana
Planta
228
663-674
2008
Arabidopsis thaliana (Q9LVF0)
brenda
Mittasch, J.; Mikolajewski, S.; Breuer, F.; Strack, D.; Milkowski, C.
Genomic microstructure and differential expression of the genes encoding UDP-glucose:sinapate glucosyltransferase (UGT84A9) in oilseed rape (Brassica napus)
Theor. Appl. Genet.
120
1485-1500
2010
Brassica napus var. napus (C1L318), Brassica napus var. napus (C1L319), Brassica napus var. napus (C1L320), Brassica napus var. napus (C1L321), Brassica napus var. napus (Q9FYU7)
brenda
Wolfram, K.; Schmidt, J.; Wray, V.; Milkowski, C.; Schliemann, W.; Strack, D.
Profiling of phenylpropanoids in transgenic low-sinapine oilseed rape (Brassica napus)
Phytochemistry
71
1076-1084
2010
Brassica napus
brenda
Hettwer, K.; Boettcher, C.; Frolov, A.; Mittasch, J.; Albert, A.; von Roepenack-Lahaye, E.; Strack, D.; Milkowski, C.
Dynamic metabolic changes in seeds and seedlings of Brassica napus (oilseed rape) suppressing UGT84A9 reveal plasticity and molecular regulation of the phenylpropanoid pathway
Phytochemistry
124
46-57
2016
Brassica napus (Q9FYU7), Brassica napus
brenda
Chen, Y.; Xu, Z.; Xiong, A.
Identification and characterization of DcUSAGT1, a UDP-glucose sinapic acid glucosyltransferase from purple carrot taproots
PLoS ONE
11
e0154938
2016
Daucus carota, Daucus carota subsp. sativus
brenda
Kajla, S.; Mukhopadhyay, A.; Pradhan, A.
Development of transgenic Brassica juncea lines for reduced seed sinapine content by perturbing phenylpropanoid pathway genes
PLoS ONE
12
e0182747
2017
Brassica juncea (A0A0M3PZA4)
brenda