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Information on EC 2.4.1.81 - flavone 7-O-beta-glucosyltransferase Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
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flavone 7-O-beta-glucosyltransferase
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UDP-glucose + 5,7,3',4'-tetrahydroxyflavone = UDP + 7-O-beta-D-glucosyl-5,7,3',4'-tetrahydroxyflavone
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hexosyl group transfer
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apigenin glycosides biosynthesis
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luteolin glycosides biosynthesis
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Flavone and flavonol biosynthesis
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UDP-glucose:5,7,3',4'-tetrahydroxyflavone 7-O-beta-D-glucosyltransferase
A number of flavones, flavanones and flavonols can function as acceptors. Different from EC 2.4.1.91 (flavonol 3-O-glucosyltransferase).
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glucosyltransferase, uridine diphosphoglucose-apigenin 7-O-
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glucosyltransferase, uridine diphosphoglucose-luteolin
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UDP-glucose-apigenin beta-glucosyltransferase
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UDP-glucosyltransferase
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UDPglucose-luteolin beta-D-glucosyltransferase
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uridine diphosphoglucose-apigenin 7-O-glucosyltransferase
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YjiC
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Swissprot
brenda
gene yjiC
UniProt
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gene yjiC
UniProt
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brenda
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TDP-glucose + luteolin
TDP + 7-O-beta-D-glucosylluteolin
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UDP-alpha-D-glucose + kaempferol
UDP + kaempferol 7-O-beta-D-glucoside
78.9% of the activity with eriodictyol
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UDP-alpha-D-glucose + quercetin
UDP + quercetin 7-O-beta-D-glucoside
64.1% of the activity with eriodictyol
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UDP-glucose + 3',4',5,7-tetrahydroxyflavone
UDP + 7-O-beta-D-glucosyl-3',4',5,7-tetrahydroxyflavone
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involved in biosynthesis of flavone glucosides
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UDP-glucose + apigenin
UDP + 4',7-O-beta-D-diglucosyl-apigenin
UDP-glucose + apigenin
UDP + 4'-O-beta-D-glucosyl-apigenin
UDP-glucose + apigenin
UDP + 7-O-beta-D-glucosyl-apigenin
UDP-glucose + eriodictyol
UDP + 7-O-beta-D-glucosyl-eriodictyol
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UDP-glucose + luteolin
UDP + 7-O-beta-D-glucosyl-luteolin
92.1% of the activity with eriodictyol
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UDP-glucose + naringenin
UDP + 7-O-beta-D-glucosyl-naringenin
71.6% of the activity with eriodictyol
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UDPglucose + 3,7,4'-trihydroxyflavone
UDP + 7-O-beta-D-glucosyl-3,7,4'trihydroxyflavone
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9% of the activity with apigenin
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UDPglucose + 5,7-dihydroxyflavanone
UDP + 7-O-beta-D-glucosyl-5,7-dihydroxyflavanone
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15% of the activity with apigenin
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UDPglucose + 7,4'-dihydroxyflavone
UDP + 7-O-beta-D-glucosyl-7,4'-dihydroxyflavone
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20% of the activity with apigenin
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UDPglucose + acacetin
UDP + 7-O-beta-D-glucosylacacetin
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24% of the activity with apigenin
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UDPglucose + apigenin
UDP + 7-O-beta-D-glucosyl-apigenin
29.6% of the activity with eriodictyol
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UDPglucose + apigenin
UDP + 7-O-beta-D-glucosylluteolin
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UDPglucose + chrysoeriol
UDP + 7-O-beta-D-glucosylchrysoeriol
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63% of the activity with apigenin
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UDPglucose + datiscetin
UDP + 7-O-beta-D-glucosyldatiscetin
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9% of the activity with apigenin
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UDPglucose + fisetin
UDP + 7-O-beta-D-glucosylfisetin
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14% of the activity with apigenin
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UDPglucose + galangin
UDP + 7-O-beta-D-glucosylgalangin
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9% of the activity with apigenin
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UDPglucose + kaempferid
UDP + 7-O-beta-D-glucosylkaempferid
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16% of the activity with apigenin
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UDPglucose + kaempferol
UDP + 7-O-beta-D-glucosylkaempferol
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11% of the activity with apigenin
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UDPglucose + luteolin
UDP + 7-O-beta-D-glucosylluteolin
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210% of the activity with apigenin
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UDPglucose + naringenin
UDP + 7-O-beta-D-glucosylnaringenin
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45% of the activity with apigenin
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UDPglucose + quercetin
UDP + 7-O-beta-D-glucosylquercetin
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16% of the activity with apigenin
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additional information
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UDP-glucose + apigenin
UDP + 4',7-O-beta-D-diglucosyl-apigenin
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UDP-glucose + apigenin
UDP + 4',7-O-beta-D-diglucosyl-apigenin
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UDP-glucose + apigenin
UDP + 4'-O-beta-D-glucosyl-apigenin
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UDP-glucose + apigenin
UDP + 4'-O-beta-D-glucosyl-apigenin
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UDP-glucose + apigenin
UDP + 7-O-beta-D-glucosyl-apigenin
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UDP-glucose + apigenin
UDP + 7-O-beta-D-glucosyl-apigenin
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additional information
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glucosylation at the phenolic groups of C-4' and C-7 positions ensuing apigenin 4'-O-glucoside, apigenin 7-O-glucoside and apigenin 4',7-O-diglucoside as the products leaving the C-5 position unglucosylated. Position of glucosylation and the chemical structures of glucosides are elucidated by liquid chromatography/mass spectroscopy and nuclear magnetic resonance spectroscopy. The UDP-glucose concentration and the pH value influence the synthesis of particular glucosides, i.e. the site of glucosylation. Formation of 7-O-beta-D-glucosyl-apigenin is higher in more alkaline conditions, whereas 4',7-O-beta-D-diglucosyl-apigenin prefers a pH range of pH 7.5-8.8. The formation of 4'-O-beta-D-glucosyl-apigenin is highest at a 3 mM concentration of UDP-glucose, while formation of 7-O-beta-D-glucosyl-apigenin is highest with a 6 mM concentration of UDP-glucose, but it decreases slightly at 9 mM concentration. Similarly, 4',7-O-beta-D-diglucosyl-apigenin formation is highest with 9 mM UDP-glucose and lowest with 3 mM UDP-glucose. Not much difference is observed in the amount of 4',7-O-beta-D-diglucosyl-apigenin between the two reactions with 6 mM and 9 mM UDP-glucose
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additional information
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glucosylation at the phenolic groups of C-4' and C-7 positions ensuing apigenin 4'-O-glucoside, apigenin 7-O-glucoside and apigenin 4',7-O-diglucoside as the products leaving the C-5 position unglucosylated. Position of glucosylation and the chemical structures of glucosides are elucidated by liquid chromatography/mass spectroscopy and nuclear magnetic resonance spectroscopy. The UDP-glucose concentration and the pH value influence the synthesis of particular glucosides, i.e. the site of glucosylation. Formation of 7-O-beta-D-glucosyl-apigenin is higher in more alkaline conditions, whereas 4',7-O-beta-D-diglucosyl-apigenin prefers a pH range of pH 7.5-8.8. The formation of 4'-O-beta-D-glucosyl-apigenin is highest at a 3 mM concentration of UDP-glucose, while formation of 7-O-beta-D-glucosyl-apigenin is highest with a 6 mM concentration of UDP-glucose, but it decreases slightly at 9 mM concentration. Similarly, 4',7-O-beta-D-diglucosyl-apigenin formation is highest with 9 mM UDP-glucose and lowest with 3 mM UDP-glucose. Not much difference is observed in the amount of 4',7-O-beta-D-diglucosyl-apigenin between the two reactions with 6 mM and 9 mM UDP-glucose
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UDP-glucose + 3',4',5,7-tetrahydroxyflavone
UDP + 7-O-beta-D-glucosyl-3',4',5,7-tetrahydroxyflavone
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involved in biosynthesis of flavone glucosides
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ethylene monomethylether
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Tris-HCl
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in 1 M Tris-HCl buffer the reaction rate is 70% of that observed in 0.1 M buffer
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bovine serum albumin
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stimulates
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0.0018
eriodictyol
pH 7.0
0.26
TDPglucose
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reaction with apigenin
0.12
UDPglucose
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reaction with apigenin
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6 - 9
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pH 6.0: about 35% of maximal activity, pH 9.0: about 50% of maximal activity
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extractable activity is drastically increased by illuminating the cells with white light and the maximum activity is reached 24 h after the onset of illumination
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high expression
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high expression
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54800
x * 54800, calculated from sequence
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x * 54800, calculated from sequence
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6.5
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rapid loss of activity below
489425
7.5 - 8.5
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most stable
489425
9.5
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above, rapid loss of activity above
489425
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3°C, t1/2: 1 month in 0.05 M Tris-HCl buffer, pH 7.5, 7 mM 2-mercaptoethanol
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recombinant His-tagged enzyme from Escherichia coli strain BL21(DE3) by nickel affinity chromatography and dialysis
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expression in Escherichia coli as a glutathione S-transferase fusion protein
gene yjiC, cloned from genomic DNA, recombinant expression of His-tagged enzyme in Escherichia coli strain BL21(DE3)
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synthesis
biotransformation of eriodictyol using Escherichi coli expressing AtGT-2
synthesis
the enzyme is used for the synthesis of apigenin glucosides, that have higher water solubility, increased chemical stability, and enhanced biological activities compared to the aglycon apigenin
synthesis
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the enzyme is used for the synthesis of apigenin glucosides, that have higher water solubility, increased chemical stability, and enhanced biological activities compared to the aglycon apigenin
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Q65JC2_BACLD
Bacillus licheniformis (strain ATCC 14580 / DSM 13 / JCM 2505 / NBRC 12200 / NCIMB 9375 / NRRL NRS-1264 / Gibson 46)
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44659
TrEMBL
U73B1_ARATH
488
54836
Swiss-Prot
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Sutter, A.; Ortmann, R.; Grisebach, H.
Purification and properties of an enzyme from cell suspension cultures of parsley catalyzing the transfer of D-glucose from UDP-D-glucose to flavonoids
Biochim. Biophys. Acta
258
71-87
1972
Petroselinum crispum
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Kim, J.H.; Kim, B.G.; Park, Y.; Ko, J.H.; Lim, C.E.; Lim, J.; Lim, Y.; Ahn, J.
Characterization of flavonoid 7-O-glucosyltransferase from Arabidopsis thaliana
Biosci. Biotechnol. Biochem.
70
1471-1477
2006
Arabidopsis thaliana (Q8VZE9)
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Gurung, R.B.; Kim, E.H.; Oh, T.J.; Sohng, J.K.
Enzymatic synthesis of apigenin glucosides by glucosyltransferase (YjiC) from Bacillus licheniformis DSM 13
Mol. Cells
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355-361
2013
Bacillus licheniformis (Q65JC2), Bacillus licheniformis DSM 13 (Q65JC2)
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