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IUBMB Comments Ternatins are a group of polyacetylated delphinidin glucosides that confer
blue color to the petals of Clitoria ternatea (butterfly pea).
This enzyme catalyses two reactions in the biosynthesis of ternatin C5: the conversion of delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside to delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3'-O-beta-D-glucoside, followed by the conversion of the later to ternatin C5, by transferring two glucosyl groups in a stepwise manner .
The expected taxonomic range for this enzyme is: Clitoria ternatea
Synonyms
3',5'-o-glucosyltransferase, ua3'5'gt, a3'5'gt,
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3',5'-O-glucosyltransferase
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UDP-glucose:anthocyanin 3',5'-glucosyltransferase
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UDP-glucose:anthocyanin 3',5'-O-glucosyltransferase
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uridine diphosphate-glucose:anthocyanin 3',5'-glucosyltransferase
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UDP-glucose + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside = UDP + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3'-O-beta-D-glucoside
UDP-glucose + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3'-O-beta-D-glucoside = UDP + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3',5'-di-O-beta-D-glucoside
UDP-glucose + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside = UDP + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3'-O-beta-D-glucoside
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UDP-glucose + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside = UDP + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3'-O-beta-D-glucoside
UDP-glucose:anthocyanin 3',5'-O-glucosyltransferase has both, UA3'GT and UA5'GT activities, highly regioselective to the 3' and 5' OH groups
UDP-glucose + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3'-O-beta-D-glucoside = UDP + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3',5'-di-O-beta-D-glucoside
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UDP-glucose + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3'-O-beta-D-glucoside = UDP + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3',5'-di-O-beta-D-glucoside
UDP-glucose:anthocyanin 3',5'-O-glucosyltransferase has both, UA3'GT and UA5'GT activities, highly regioselective to the 3' and 5' OH groups
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UDP-glucose:delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside 3'-O-glucosyltransferase
Ternatins are a group of polyacetylated delphinidin glucosides that confer
blue color to the petals of Clitoria ternatea (butterfly pea).
This enzyme catalyses two reactions in the biosynthesis of ternatin C5: the conversion of delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside to delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3'-O-beta-D-glucoside, followed by the conversion of the later to ternatin C5, by transferring two glucosyl groups in a stepwise manner [1].
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2 UDP-glucose + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside
2 UDP + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3',5'-di-O-beta-D-glucoside
UDP-D-glucose + cyanidin 3-O-(6-O-malonyl)-beta-D-glucoside
UDP + cyanidin 3-O-(6-O-malonyl)-beta-D-glucoside 3'-O-beta-D-glucoside
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24.3% relative activity compared to delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside as substrate
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UDP-D-glucose + delphinidin 3,3'-di-O-beta-D-glucoside
UDP + delphinidin 3,3',5'-tri-O-beta-D-glucoside
3.3% relative activity compared to delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside as substrate
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UDP-D-glucose + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside
UDP + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3'-O-beta-glucoside
UDP-D-glucose + delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3'-O-beta-D-glucoside
UDP + delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3',5'-di-O-beta-D-glucoside
UDP-D-glucose + delphinidin 3-O-beta-D-glucoside
UDP + delphinidin 3,3'-di-O-beta-D-glucoside
3.9% relative activity compared to delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside as substrate
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UDP-D-glucose + petunidin 3-O-(6''-O-malonyl)-beta-D-glucoside
UDP + petunidin 3-O-(6''-O-malonyl)-beta-D-glucoside 5'-O-beta-D-glucoside
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123% relative activity compared to delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside as substrate
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additional information
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2 UDP-glucose + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside
2 UDP + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3',5'-di-O-beta-D-glucoside
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2 UDP-glucose + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside
2 UDP + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3',5'-di-O-beta-D-glucoside
the enzyme is involved in the anthocyanin biosynthetic pathway
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UDP-D-glucose + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside
UDP + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3'-O-beta-glucoside
3'-O-glucosyltransferase activity, first reaction of UA3'5'GT in the biosynthesis of ternatins, transferring two glucosyl groups in a stepwise manner
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UDP-D-glucose + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside
UDP + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3'-O-beta-glucoside
3'-O-glucosyltransferase activity, catalyzed by UA3'5'GT
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UDP-D-glucose + delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3'-O-beta-D-glucoside
UDP + delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3',5'-di-O-beta-D-glucoside
5'-O-glucosyltransferase activity, second reaction of UA3'5'GT in the biosynthesis of ternatins, transferring two glucosyl groups in a stepwise manner
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UDP-D-glucose + delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3'-O-beta-D-glucoside
UDP + delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3',5'-di-O-beta-D-glucoside
5'-O-glucosyltransferase activity, catalyzed by UA3'5'GT
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additional information
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no activity detected with cyanidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3'-O-beta-D-glucoside, pelargonidin 3-O-(6''-O-malonyl)-beta-D-glucoside, delphinidin 3,5-di-O-beta-D-glucoside. No activity with delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3'-O-beta-D-glucoside using UDP-D-galactose as sugar donor
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additional information
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no activity detected with cyanidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3'-O-beta-D-glucoside, pelargonidin 3-O-(6''-O-malonyl)-beta-D-glucoside, delphinidin 3,5-di-O-beta-D-glucoside. No activity with delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3'-O-beta-D-glucoside using UDP-D-galactose as sugar donor
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2 UDP-glucose + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside
2 UDP + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3',5'-di-O-beta-D-glucoside
the enzyme is involved in the anthocyanin biosynthetic pathway
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UDP-D-glucose + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside
UDP + delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3'-O-beta-glucoside
3'-O-glucosyltransferase activity, first reaction of UA3'5'GT in the biosynthesis of ternatins, transferring two glucosyl groups in a stepwise manner
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UDP-D-glucose + delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3'-O-beta-D-glucoside
UDP + delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3',5'-di-O-beta-D-glucoside
5'-O-glucosyltransferase activity, second reaction of UA3'5'GT in the biosynthesis of ternatins, transferring two glucosyl groups in a stepwise manner
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CaCl2
10 mM, 82% activity retains
EDTA
10 mM, 75% activity retains
FeCl2
10 mM, 73% activity retains
MgCl2
10 mM, 88% activity retains
ZnCl2
10 mM, 62% activity retains
additional information
completely inhibited by 10 mM CuCl2
additional information
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completely inhibited by 10 mM CuCl2
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diethyldicarbonate
10 mM, 16% activity retains
dithioerythritol
10 mM, 83% activity retains
iodoacetate
10 mM, 84% activity retains
N-ethylmaleimide
10 mM, 16% activity retains
p-chloromercuribenzoic acid
10 mM, completely inhibited
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0.0389
delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside
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0.138
delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3'-O-beta-glucoside
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1.49 - 6.18
UDP-D-glucose
1.49
UDP-D-glucose
apparent, delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside as saturated substrate
6.18
UDP-D-glucose
apparent, delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3'-O-beta-glucoside as saturated substrate
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4.4
delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside
UDP-glucose as sugar donor
5.4
delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3'-O-beta-glucoside
UDP-glucose as sugar donor
4.9
UDP-D-glucose
delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3'-O-beta-glucoside as substrate
5.1
UDP-D-glucose
delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside as substrate
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0.000276
UA5'GT activity, substrate: delphinidin 3,3'-di-O-beta-D-glucoside
0.000324
UA3'GT activity, substrate: delphinidin 3-O-beta-D-glucoside
0.002
UA3'GT activity, substrate: cyanidin 3-O-(6''-O-malonyl)-beta-D-glucoside
0.01
UA5'GT activity, substrate: petunidin 3-O-(6''-O-malonyl)-beta-D-glucoside
0.98
UA3'GT activity, substrate: delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside
2.29
UA5'GT activity, substrate: delphinidin 3-O-(6''-O-malonyl)-beta-D-glucoside-3'-O-beta-glucoside
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7.5 - 8
pH 7.5 and pH 8.0 in potassium phosphate buffer and Tris-HCl buffer, respectively
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UniProt
brenda
gene An3'5'GT; butterfly pea
UniProt
brenda
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brenda
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metabolism
the enzyme is involved in the anthocyanin biosynthetic pathway
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A4F1Q6_CLITE
447
0
48651
TrEMBL
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58000
1 * 58000, SDS-PAGE
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monomer
1 * 58000, SDS-PAGE
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from petals, which accumulate polyacylated anthocyanins and ternatins, using ammonium sulfate precipitation, DEAE Toyopearl, Reactive yellow 86, Cellufine HAP, and Mono Q chromatography, UA5'GT: 1007fold purified, UA3'GT: 346 fold purified
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Clitoria ternatea gene CtA3'5'GT encoding UDP-glucose:anthocyanin 3',5'-glucosyltransferase is introduced into Chrysanthemum by using binary vector pB249. Although transgenic plants expressing CtA3'5'GT are obtained, their flowers do not show a color change to bluish hue. Two transgenes, namely, CamF3'5'H and CtA3'5'GT, are enough to generate blue chrysanthemums: The 3',5'-diglucosylated delphinidin exhibits a blue color by intermolecular association with flavone glucosides under the weakly acidic pH conditions of general flower petals
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additional information
creation of blue flowers in ornamental plants. Introduction of the F3'5'H gene encoding flavonoid 3',5'-hydroxylase can produce delphinidin in various flowers such as roses and carnations, turning the flower color purple or violet. Blue chrysanthemum is produced by introducing the A3'5'GT gene encoding anthocyanin 3',5'-O-glucosyltransferase, in addition to F3'5'H encoding flavonoid 3',5'-hydroxylase, into the host plant. The B-ring glucosylated delphinidin-based anthocyanin that is synthesized by the two transgenes develops blue coloration by co-pigmentation with colorless flavone glycosides naturally present in the ray floret of chrysanthemum
additional information
creation of blue flowers in ornamental plants. Two transgenes, namely, CamF3'5'H and CtA3'5'GT, are enough to generate blue chrysanthemum: The 3',5'-diglucosylated delphinidin exhibits a blue color by intermolecular association with flavone glucosides under the weakly acidic pH conditions of general flower petals
additional information
generation of blue Chrysanthemums through genetic engineering. The blue coloration of the Chrysanthemum is accomplished by constructing functional genes producing flavonoid 3',5'-hydroxylase and anthocyanin 3',5'-O-glucosyltransferase. Accumulation of 3',5'-O-glucosylated delphinidin-based anthocyanins synthesized by the transgenes leads to the development of blue color via intermolecular copigmentation with flavone glycosides present in chrysanthemum petal
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Kogawa, K.; Kato, N.; Kazuma, K.; Noda, N.; Suzuki, M.
Purification and characterization of UDP-glucose: anthocyanin 3',5'-O-glucosyltransferase from Clitoria ternatea
Planta
226
1501-1509
2007
Clitoria ternatea (A4F1Q6), Clitoria ternatea
brenda
Nodaa, N.
Breeding of blue chrysanthemums by genetic engineering
Acta Hortic.
1237
7-12
2019
Clitoria ternatea (A4F1Q6)
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brenda
Noda, N.
Recent advances in the research and development of blue flowers
Breed. Sci.
68
79-87
2018
Clitoria ternatea (A4F1Q6)
brenda
Noda, N.; Yoshioka, S.; Kishimoto, S.; Nakayama, M.; Douzono, M.; Tanaka, Y.; Aida, R.
Generation of blue chrysanthemums by anthocyanin B-ring hydroxylation and glucosylation and its coloration mechanism
Sci. Adv.
3
e1602785
2017
Clitoria ternatea (A4F1Q6)
brenda
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