Information on EC 2.3.1.215 - anthocyanidin 3-O-glucoside 6''-O-acyltransferase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.3.1.215
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RECOMMENDED NAME
GeneOntology No.
anthocyanidin 3-O-glucoside 6''-O-acyltransferase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
4-hydroxycinnamoyl-CoA + an anthocyanidin 3-O-beta-D-glucoside = CoA + an anthocyanidin 3-O-[6-O-(4-hydroxycinnamoyl)-beta-D-glucoside]
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
anthocyanidin acylglucoside and acylsambubioside biosynthesis
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Anthocyanin biosynthesis
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shisonin biosynthesis
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superpathway of anthocyanin biosynthesis (from cyanidin and cyanidin 3-O-glucoside)
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SYSTEMATIC NAME
IUBMB Comments
4-hydroxycinnamoyl-CoA:anthocyanin-3-O-glucoside 6''-O-acyltransferase
Isolated from the plants Perilla frutescens and Gentiana triflora (clustered gentian). Acts on a range of anthocyanidin 3-O-glucosides, 3,5-di-O-glucosides and cyanidin 3-rutinoside. It did not act on delphinidin 3,3',7-tri-O-glucoside. Recombinant Perilla frutescens enzyme could utilize caffeoyl-CoA but not malonyl-CoA as alternative acyl donor.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
isoforms Ih3AT1, Ih3AT2
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
constitutive expression of 3AT in tobacco results in the production of acylated anthocyanins
additional information
-
red leaves accumulate cyanidin 3-(6-O-4-coumaroyl-beta-D-glucoside)-5-(6-O-malonyl-beta-D-glucoside)
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
4-hydroxycinnamoyl-CoA + cyanidin 3,5-O-beta-D-diglucoside
CoA + cyanidin 3-O-[6-O-(4-hydroxycinnamoyl)-beta-D-glucosyl]-5-O-beta-D-glucoside
show the reaction diagram
-
-
-
?
4-hydroxycinnamoyl-CoA + cyanidin 3-O-beta-D-glucoside
CoA + ?
show the reaction diagram
-
-
-
-
?
4-hydroxycinnamoyl-CoA + cyanidin 3-O-beta-D-glucoside
CoA + cyanidin 3-O-[6-O-(4-hydroxycinnamoyl)-beta-D-glucoside]
show the reaction diagram
-
-
-
?
4-hydroxycinnamoyl-CoA + delphinidin 3,5-O-beta-D-diglucoside
CoA + delphinidin 3-O-(4-coumaroyl)-beta-D-glucoside-5-O-beta-D-glucoside
show the reaction diagram
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-
-
?
4-hydroxycinnamoyl-CoA + delphinidin 3-O-beta-D-glucoside
CoA + ?
show the reaction diagram
-
-
-
-
?
4-hydroxycinnamoyl-CoA + delphinidin 3-O-beta-D-glucoside
CoA + delphinidin 3-O-[6-O-(4-hydroxycinnamoyl)-beta-D-glucoside]
show the reaction diagram
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-
-
?
4-hydroxycinnamoyl-CoA + pelargonidin 3,5-O-beta-D-diglucoside
CoA + pelargonidin 3-O-[6-O-(4-hydroxycinnamoyl)-beta-D-glucosyl]-5-O-beta-D-glucoside
show the reaction diagram
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-
-
?
4-hydroxycinnamoyl-CoA + pelargonidin 3-O-beta-D-glucoside
CoA + ?
show the reaction diagram
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-
-
-
?
4-hydroxycinnamoyl-CoA + pelargonidin 3-O-beta-D-glucoside
CoA + pelargonidin 3-O-[6-O-(4-hydroxycinnamoyl)-beta-D-glucoside]
show the reaction diagram
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-
-
?
anthocyanidin 3-rhamnosylglucoside-5-glucoside + p-coumaroyl-CoA
CoA + anthocyanidin 3-(p-coumaroyl)rhamnosylglucoside-5-glucoside
show the reaction diagram
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-
-
-
?
caffeoyl-CoA + cyanidin 3,5-O-beta-D-diglucoside
CoA + cyanidin 3-O-[6-O-caffeoyl-beta-D-glucosyl]-5-O-beta-D-glucoside
show the reaction diagram
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-
-
?
caffeoyl-CoA + cyanidin 3-O-beta-D-glucoside
CoA + ?
show the reaction diagram
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-
-
-
?
caffeoyl-CoA + cyanidin 3-O-beta-D-glucoside
CoA + cyanidin 3-O-[6-O-caffeoyl-beta-D-glucoside]
show the reaction diagram
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-
-
?
caffeoyl-CoA + delphinidin 3,5-O-beta-D-diglucoside
CoA + delphinidin 3,5-O-[6-O-caffeoyl-beta-D-diglucoside]
show the reaction diagram
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-
-
?
caffeoyl-CoA + delphinidin 3-O-beta-D-glucoside
CoA + ?
show the reaction diagram
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-
-
-
?
caffeoyl-CoA + delphinidin 3-O-beta-D-glucoside
CoA + delphinidin 3-O-[6-O-caffeoyl-beta-D-glucoside]
show the reaction diagram
-
-
-
?
caffeoyl-CoA + pelargonidin 3,5-O-beta-D-diglucoside
CoA + pelargonidin 3-O-[6-O-caffeoyl-beta-D-glucoside]-5-O-beta-D-glucoside
show the reaction diagram
-
-
-
?
caffeoyl-CoA + pelargonidin 3-O-beta-D-glucoside
CoA + ?
show the reaction diagram
-
-
-
-
?
caffeoyl-CoA + pelargonidin 3-O-beta-D-glucoside
CoA + pelargonidin 3-O-[6-O-caffeoyl-beta-D-glucoside]
show the reaction diagram
-
-
-
?
cyanidin 3-O,5-O-beta-D-diglucoside + acetyl-CoA
CoA + cyanidin-3-O-(6-O-acetyl)-beta-D-glucosyl-5-O-beta-D-glucoside
show the reaction diagram
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-
-
?
cyanidin 3-O-beta-D-glucoside + acetyl-CoA
CoA + cyanidin 3-O-(6-O-acetyl)-beta-D-glucoside
show the reaction diagram
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-
-
?
delphinidin 3-O-beta-D-glucoside + acetyl-CoA
CoA + delphinidin 3-O-(6-O-acetyl)-beta-D-glucoside
show the reaction diagram
-
-
-
?
delphinidin 3-rhamnosylglucoside-5-glucoside + p-coumaroyl-CoA
CoA + delphinidin 3-(p-coumaroyl)rhamnosylglucoside-5-glucoside
show the reaction diagram
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-
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?
malvidin 3-O-beta-D-glucoside + acetyl-CoA
CoA + malvidin 3-O-(6-O-acetyl)-beta-D-glucoside
show the reaction diagram
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-
-
?
malvidin 3-O-beta-D-glucoside + caffeoyl-CoA
CoA + malvidin 3-O-(6-O-caffeoyl)-beta-D-glucoside
show the reaction diagram
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-
-
?
malvidin 3-O-beta-D-glucoside + coumaroyl-CoA
CoA + malvidin 3-O-(6-O-coumaroyl)-beta-D-glucoside
show the reaction diagram
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-
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?
malvidin 3-O-beta-D-glucoside + malonyl-CoA
CoA + malvidin 3-O-(6-O-malonyl)-beta-D-glucoside
show the reaction diagram
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-
-
?
malvidin 3-rhamnosylglucoside-5-glucoside + p-coumaroyl-CoA
CoA + malvidin 3-(p-coumaroyl)rhamnosylglucoside-5-glucoside
show the reaction diagram
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-
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-
?
peonidin 3-O-beta-D-glucoside + acetyl-CoA
CoA + peonidin 3-O-(6-O-acetyl)-beta-D-glucoside
show the reaction diagram
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-
-
?
petunidin 3-rhamnosylglucoside-5-glucoside + p-coumaroyl-CoA
CoA + petunidin 3-(p-coumaroyl)rhamnosylglucoside-5-glucoside
show the reaction diagram
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?
additional information
?
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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
4-hydroxycinnamoyl-CoA + cyanidin 3-O-beta-D-glucoside
CoA + ?
show the reaction diagram
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-
-
-
?
4-hydroxycinnamoyl-CoA + delphinidin 3-O-beta-D-glucoside
CoA + ?
show the reaction diagram
-
-
-
-
?
4-hydroxycinnamoyl-CoA + pelargonidin 3-O-beta-D-glucoside
CoA + ?
show the reaction diagram
-
-
-
-
?
caffeoyl-CoA + cyanidin 3-O-beta-D-glucoside
CoA + ?
show the reaction diagram
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-
-
-
?
caffeoyl-CoA + delphinidin 3-O-beta-D-glucoside
CoA + ?
show the reaction diagram
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-
-
-
?
caffeoyl-CoA + pelargonidin 3-O-beta-D-glucoside
CoA + ?
show the reaction diagram
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-
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?
additional information
?
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lower Km values for anthocyanidin 3-O-beta-D-glucoside than 3,5-O-beta-D-diglucoside may indicate that acylation of cyanidin 3-O-beta-D-glucoside precedes 5-O-glucosylation in vivo
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
diethyl dicarbonate
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N-ethylmaleimide
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0169
acetyl-CoA
pH 6.5, 30°C
0.0041
caffeoyl-CoA
pH 6.5, 30°C
0.0012
coumaroyl-CoA
pH 6.5, 30°C
0.064
cyanidin 3-O,5-O-beta-D-diglucoside
pH 6.5, 30°C
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0.506
cyanidin 3-O-beta-D-glucoside
pH 6.5, 30°C
0.765
delphinidin 3-O-beta-D-glucoside
pH 6.5, 30°C
0.588
malonyl-CoA
pH 6.5, 30°C
0.098
malvidin 3-O-beta-D-glucoside
pH 6.5, 30°C
0.079
peonidin 3-O-beta-D-glucoside
pH 6.5, 30°C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.11
acetyl-CoA
Vitis vinifera
D7TU67
pH 6.5, 30°C
0.29
caffeoyl-CoA
Vitis vinifera
D7TU67
pH 6.5, 30°C
0.13
coumaroyl-CoA
Vitis vinifera
D7TU67
pH 6.5, 30°C
0.18
cyanidin 3-O,5-O-beta-D-diglucoside
Vitis vinifera
D7TU67
pH 6.5, 30°C
-
77
cyanidin 3-O-beta-D-glucoside
Vitis vinifera
D7TU67
pH 6.5, 30°C
67.89
delphinidin 3-O-beta-D-glucoside
Vitis vinifera
D7TU67
pH 6.5, 30°C
0.92
malonyl-CoA
Vitis vinifera
D7TU67
pH 6.5, 30°C
13.92
malvidin 3-O-beta-D-glucoside
Vitis vinifera
D7TU67
pH 6.5, 30°C
14.2
peonidin 3-O-beta-D-glucoside
Vitis vinifera
D7TU67
pH 6.5, 30°C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
80
acetyl-CoA
Vitis vinifera
D7TU67
pH 6.5, 30°C
29
70
caffeoyl-CoA
Vitis vinifera
D7TU67
pH 6.5, 30°C
537
100
coumaroyl-CoA
Vitis vinifera
D7TU67
pH 6.5, 30°C
5236
3
cyanidin 3-O,5-O-beta-D-diglucoside
Vitis vinifera
D7TU67
pH 6.5, 30°C
210545
150
cyanidin 3-O-beta-D-glucoside
Vitis vinifera
D7TU67
pH 6.5, 30°C
1428
90
delphinidin 3-O-beta-D-glucoside
Vitis vinifera
D7TU67
pH 6.5, 30°C
4983
1.6
malonyl-CoA
Vitis vinifera
D7TU67
pH 6.5, 30°C
76
150
malvidin 3-O-beta-D-glucoside
Vitis vinifera
D7TU67
pH 6.5, 30°C
17666
180
peonidin 3-O-beta-D-glucoside
Vitis vinifera
D7TU67
pH 6.5, 30°C
13711
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.5
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substrate malvidin 3-rhamnosylglucoside-5-glucoside, pH 6.5, 35°C
1.54
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substrate petunidin 3-rhamnosylglucoside-5-glucoside, pH 6.5, 35°C
1.74
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substrate delphinidin 3-rhamnosylglucoside-5-glucoside, pH 6.5, 35°C
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.61
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both isoform Ih3AT1 and Ih3AT2, calculated
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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expression in flower buds and fully opened flowers
Manually annotated by BRENDA team
additional information
-
no expression in leaf
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
47706
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x * 47706, isoform Ih3AT1, x * 47760, isoform Ih3AT2, calculated, x * 50000, both isoforms, SDS-PAGE
47760
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x * 47706, isoform Ih3AT1, x * 47760, isoform Ih3AT2, calculated, x * 50000, both isoforms, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
gene PfAT208, DNA and amino acid sequence determination and analysis, sequence ccomparison, expression in Escherichia coli as fusion protein with beta-galactosidase
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
transcription factor MYBA is a positive regulator of the later stages of anthocyanin synthesis, modification, and transport in cv Shiraz. Anthocyanidin 3-O-glucoside 6''-O-acyltransferase is upregulated by MYBA
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
protein sequence changes and gene expression patterns of 3AT correlate with the absence of acylated anthocyanins in cv Pinot Noir and pale-fruited cv Cabernet Sauvignon mutants