Information on EC 2.3.1.171 - anthocyanin 6''-O-malonyltransferase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.3.1.171
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RECOMMENDED NAME
GeneOntology No.
anthocyanin 6''-O-malonyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
malonyl-CoA + an anthocyanidin 3-O-beta-D-glucoside = CoA + an anthocyanidin 3-O-(6-O-malonyl-beta-D-glucoside)
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Anthocyanin biosynthesis
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cyanidin dimalonylglucoside biosynthesis
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pelargonidin conjugates biosynthesis
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ternatin C5 biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
malonyl-CoA:anthocyanidin-3-O-beta-D-glucoside 6''-O-malonyltransferase
Acts on pelargonidin 3-O-glucoside in dahlia (Dahlia variabilis), delphinidin 3-O-glucoside, and on cyanidin 3-O-glucoside in transgenic petunia (Petunia hybrida).
CAS REGISTRY NUMBER
COMMENTARY hide
111070-07-6
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
glutaryl-CoA + pelargonidin 3-O-beta-D-glucoside
CoA + pelargonidin 3-O-(6-O-glutaryl-beta-D-glucoside)
show the reaction diagram
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50% of the activity with malonyl-CoA
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?
malonyl-CoA + cyanidin 3-O-beta-D-glucoside
CoA + cyanidin 3-O-(6-O-malonyl-beta-D-glucoside)
show the reaction diagram
malonyl-CoA + delphinidin 3,5-di-O-beta-D-glucoside
CoA + ?
show the reaction diagram
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10% of the activity with pelargonidin 3-O-glucoside
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?
malonyl-CoA + delphinidin 3-O-beta-D-glucoside
CoA + delphinidin 3-O-(6-malonyl-beta-D-glucoside)
show the reaction diagram
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because the reaction product delphinidin 3-O-6'‘-malonylglucoside, is a part of cinerarin biosynthesis, it is highly likely that Sc3MaT is involved in the biosynthesis of cinerarin
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?
malonyl-CoA + delphinidin 3-O-beta-D-glucoside
CoA + delphinidin 3-O-(6-O-malonyl-beta-D-glucoside)
show the reaction diagram
malonyl-CoA + malvidin 3-O-beta-D-glucoside
CoA + malvidin 3-O-(6-O-malonyl-beta-D-glucoside)
show the reaction diagram
malonyl-CoA + pelargonidin 3-O-beta-D-glucoside
CoA + pelargonidin 3-O-(6-O-malonyl-beta-D-glucoside)
show the reaction diagram
malonyl-CoA + peonidin 3-O-beta-D-glucoside
CoA + peonidin 3-O-(6-O-malonyl-beta-D-glucoside)
show the reaction diagram
malonyl-CoA + petunidin 3-O-beta-D-glucoside
CoA + petunidin 3-O-(6-O-malonyl-beta-D-glucoside)
show the reaction diagram
malonyl-CoA + quercetin 3-O-beta-D-glucoside
CoA + quercetin 3-O-(6-O-malonyl-beta-D-glucoside)
show the reaction diagram
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?
methylmalonyl-CoA + cyanidin 3-O-beta-D-glucoside
CoA + cyanidin 3-O-(6-O-methylmalonyl-beta-D-glucoside)
show the reaction diagram
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?
methylmalonyl-CoA + pelargonidin 3-O-beta-D-glucoside
CoA + pelargonidin 3-O-(6-O-methylmalonyl-beta-D-glucoside)
show the reaction diagram
succinyl-CoA + cyanidin 3-O-beta-D-glucoside
CoA + cyanidin 3-O-(6-O-succinyl-beta-D-glucoside)
show the reaction diagram
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7% of the activity with malonyl-CoA
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?
succinyl-CoA + cyanidin 3-O-beta-D-glucoside
CoA + succinyl 3-O-(6-O-malonyl-beta-D-glucoside)
show the reaction diagram
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?
succinyl-CoA + pelargonidin 3-O-beta-D-glucoside
CoA + pelargonidin 3-O-(6-O-succinyl-beta-D-glucoside)
show the reaction diagram
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
malonyl-CoA + delphinidin 3-O-beta-D-glucoside
CoA + delphinidin 3-O-(6-malonyl-beta-D-glucoside)
show the reaction diagram
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because the reaction product delphinidin 3-O-6'‘-malonylglucoside, is a part of cinerarin biosynthesis, it is highly likely that Sc3MaT is involved in the biosynthesis of cinerarin
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?
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
acetyl-CoA
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0.1 mM, 63% inhibition
CaCl2
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1 mM, 20% inhibition
CdCl2
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0.1 mM, 48% loss of activity
CoCl2
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1 mM, 9% inhibition
CuCl2
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0.1 mM, complete inhibition
CuSO4
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1 mM, 80% inhibition
diethyldicarbonate
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1 mM, 45% inhibition
diethyldithiocarbamate
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2 mM, 36% inhibition
EDTA
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2 mM, 34% inhibition
Fe2+
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0.1 mM, 64% inhibition
FeSO4
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1 mM, 45% inhibition
Hg2+
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0.1 mM, 65% inhibition
HgCl2
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0.1 mM, complete inhibition
KCN
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1 mM, 26% inhibition
MgCl2
MnCl2
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1 mM, 28% inhibition
PCMB
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0.2 mM, 64% inhibition
ZnCl2
ZnSO4
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1 mM, 46% inhibition
additional information
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0.1 mM EDTA or 0.1 mM CaCl2, CoCl2, FeCl2, MnCl2, NiCl2 or SnCl2 have negligible effects on the enzyme activity
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0028
cyanidin 3-O-beta-D-glucoside
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0.0041 - 0.061
malonyl-CoA
0.011 - 0.0467
pelargonidin 3-O-beta-D-glucoside
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.2 - 11.1
cyanidin 3-O-beta-D-glucoside
7.3 - 8.8
malonyl-CoA
7.3 - 8.8
pelargonidin 3-O-beta-D-glucoside
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.2 - 8.7
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50% of maximal activity at pH 6.2 and pH 8.7
6.4 - 9.7
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50% of maximal activity at pH 6.4 and at pH 9.7
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30 - 80
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50% of maximal activity at 30°C and at 80°C, 0°C: 17% of maximal activity activity
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
51224
x * 51224, calculation from nucleotide sequence
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 51224, calculation from nucleotide sequence
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 7.5
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pH 7.0, 20 min, stable
656963
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
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pH 7.0, 20 min, stable below
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, enzyme preparation can be stored for several weeks without appreciable loss of activity
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed as recombinant protein in Escherichia coli, together with other enzymes of the anthocyanidin 3-O-glucoside biosynthetic pathway
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expression in Escherichia coli
expression in Escherichia coli JM109 under the control of T5 promoter as an in-frame N-terminal fusion with a His6 tag
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expression in Escherichia coli. Creation of transgenic Petunia hybrida harboring Dv3MaT cDNA
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
A38P
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mutant in 3-O-glucoside-6’’-malonyltransferase containing regions A and C of anthocyanidin 3-O-glucoside-3’’,6’’-dimalonyltransferase, threefold decrease in 3-O-glucoside-6’’-malonyltransferase activity, anthocyanidin 3-O-glucoside-3’’,6’’-dimalonyltransferase activity is 50% of 3-O-glucoside-3’’,6’’-dimalonyltransferase wild-type
A413T
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mutant in 3-O-glucoside-6’’-malonyltransferase containing regions A and C of anthocyanidin 3-O-glucoside-3’’,6’’-dimalonyltransferase, fivefold decrease in 3-O-glucoside-6’’-malonyltransferase activity, anthocyanidin 3-O-glucoside-3’’,6’’-dimalonyltransferase activity is 50% of 3-O-glucoside-3’’,6’’-dimalonyltransferase wild-type
K419N
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mutant in 3-O-glucoside-6’’-malonyltransferase containing regions A and C of anthocyanidin 3-O-glucoside-3’’,6’’-dimalonyltransferase, 50% decrease in 3-O-glucoside-6’’-malonyltransferase activity, anthocyanidin 3-O-glucoside-3’’,6’’-dimalonyltransferase activity is 70% of 3-O-glucoside-3’’,6’’-dimalonyltransferase wild-type
L37V
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mutant in 3-O-glucoside-6’’-malonyltransferase containing regions A and C of anthocyanidin 3-O-glucoside-3’’,6’’-dimalonyltransferase, threefold decrease in 3-O-glucoside-6’’-malonyltransferase activity, anthocyanidin 3-O-glucoside-3’’,6’’-dimalonyltransferase activity similar to 3-O-glucoside-3’’,6’’-dimalonyltransferase wild-type
Q51P
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mutant in 3-O-glucoside-6’’-malonyltransferase containing regions A and C of anthocyanidin 3-O-glucoside-3’’,6’’-dimalonyltransferase, 2.5fold decrease in 3-O-glucoside-6’’-malonyltransferase activity, anthocyanidin 3-O-glucoside-3’’,6’’-dimalonyltransferase activity is 50% of 3-O-glucoside-3’’,6’’-dimalonyltransferase wild-type
T35G
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mutant in 3-O-glucoside-6’’-malonyltransferase containing regions A and C of anthocyanidin 3-O-glucoside-3’’,6’’-dimalonyltransferase, sixfold decrease in 3-O-glucoside-6’’-malonyltransferase activity, increase in anthocyanidin 3-O-glucoside-3’’,6’’-dimalonyltransferase activity
Y411N
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mutant in 3-O-glucoside-6’’-malonyltransferase containing regions A and C of anthocyanidin 3-O-glucoside-3’’,6’’-dimalonyltransferase, ninefold decrease in 3-O-glucoside-6’’-malonyltransferase activity, no anthocyanidin 3-O-glucoside-3’’,6’’-dimalonyltransferase activity
biotechnology
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production of anthocyanins to use their anti-oxidative, anti-inflammatory, anti-cancer, anti-obesity, anti-diabetic, and cardioprotective properties
medicine
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production of anthocyanins to use their anti-oxidative, anti-inflammatory, anti-cancer, anti-obesity, anti-diabetic, and cardioprotective properties
synthesis
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production of anthocyanins to use their anti-oxidative, anti-inflammatory, anti-cancer, anti-obesity, anti-diabetic, and cardioprotective properties
additional information
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swapping of regions A, B and C of anthocyanidin 3-O-glucoside-6’’-malonyltransferase and anthocyanidin 3-O-glucoside-3’’,6’’-dimalonyltransferase and identification of amino acid residues that are important for anthocyanidin 3-O-glucoside-3’’,6’’-dimalonyltransferase activity in regions A and C
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
agriculture