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Enzyme Nomenclature
Information on EC 2.3.1.172 - anthocyanin 5-O-glucoside 6'''-O-malonyltransferase
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
2.3.1.172
-
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RECOMMENDED NAME
GeneOntology No.
anthocyanin 5-O-glucoside 6'''-O-malonyltransferase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
malonyl-CoA + pelargonidin 3-O-(6-caffeoyl-beta-D-glucoside) 5-O-beta-D-glucoside = CoA + 4'''-demalonylsalvianin
malonyl-CoA + pelargonidin 3-O-(6-caffeoyl-beta-D-glucoside) 5-O-beta-D-glucoside = CoA + 4'''-demalonylsalvianin
reaction mechanism, kinetic mechanism
-
malonyl-CoA + pelargonidin 3-O-(6-caffeoyl-beta-D-glucoside) 5-O-beta-D-glucoside = CoA + 4'''-demalonylsalvianin
specific for the penultimate step in salvianin biosynthesis, the enzyme also catalyses the malonylation of shisonin to malonylshisonin [cyanidin 3-O-(6''-O-p-coumaryl-beta-D-glucoside)-5-(6'''-O-malonyl-beta-D-glucoside)], the compounds 4'''-demalonylsalvianin, salvianin, pelargonidin 3,5-diglucoside and delphinidin 3,5-diglucoside cannot act as substrates
-
malonyl-CoA + pelargonidin 3-O-(6-caffeoyl-beta-D-glucoside) 5-O-beta-D-glucoside = CoA + 4'''-demalonylsalvianin
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malonylation
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
malonyl-CoA:pelargonidin-3-O-(6-caffeoyl-beta-D-glucoside)-5-O-beta-D-glucoside 6'''-O-malonyltransferase
Specific for the penultimate step in salvianin biosynthesis. The enzyme also catalyses the malonylation of shisonin to malonylshisonin [cyanidin 3-O-(6''-O-p-coumaryl-beta-D-glucoside)-5-(6'''-O-malonyl-beta-D-glucoside)]. The compounds 4'''-demalonylsalvianin, salvianin, pelargonidin 3,5-diglucoside and delphinidin 3,5-diglucoside cannot act as substrates.
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CAS REGISTRY NUMBER
COMMENTARY
380229-66-3
-
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
acetyl-CoA + shisonin
CoA + acetylshisonin
-
2% of the activity with malonyl-CoA as acyl donor
-
-
?
malonyl-CoA + cyanidin 3-O-[[2-O-(2-O-sinapoyl)-beta-D-xylosyl]-6-O-(6-O-(4-coumaroyl)-beta-D-glucoside)] 5-O-beta-D-glucoside
CoA + cyanidin 3-O-[[2-O-(2-O-sinapoyl)-beta-D-xylosyl]-6-O-(6-O-(4-coumaroyl)-beta-D-glucoside)] 5-O-(6-O-malonyl)-beta-D-glucoside
-
-
-
?
malonyl-CoA + cyanidin 3-O-[[2-O-beta-D-xylosyl]-6-O-(6-O-(4-coumaroyl)-beta-D-glucoside)] 5-O-beta-D-glucoside
CoA + cyanidin 3-O-[[2-O-beta-D-xylosyl]-6-O-(6-O-(4-coumaroyl)-beta-D-glucoside)] 5-O-(6-O-malonyl)-beta-D-glucoside
-
-
-
?
malonyl-CoA + cyanin
CoA + cyanidin 3-O-beta-D-glucoside 5-O-(6-O-malonyl)-beta-D-glucoside
-
-
-
?
malonyl-CoA + malvin
CoA + malvidin 3-O-beta-D-glucoside 5-O-(6-O-malonyl)-beta-D-glucoside
-
-
-
?
malonyl-CoA + pelargonidin 3-O-(6-caffeoyl-beta-D-glucoside) 5-O-beta-D-glucoside
CoA + 4'''-demalonylsalvianin
malonyl-CoA + shisonin
CoA + 6'''-malonylshisonin
-
Ss5MaT1 catalyzes the regiospecific transfer of the malonyl group from malonyl-CoA to the 6'''-hydroxyl group of the 5-glucosyl moiety of shisonin, enyzme catalyzes exclusively the monomalonylation of shisonin, strong acyl donor preference for malonyl-CoA
-
-
?
malonyl-CoA + shisonin
CoA + malonylshisonin
Ss5MaT1 specifically catalyzes the malonylation of the 6'''-hydroxyl group of the 5-glucosyl moiety
-
-
?
methylmalonyl-CoA + shisonin
CoA + methylmalonylshisonin
-
3% of the activity with malonyl-CoA as acyl donor
-
-
?
succinyl-CoA + shisonin
CoA + succinylshisonin
-
49% of the activity with malonyl-CoA as acyl donor
-
-
?
malonyl-CoA + pelargonidin 3-O-(6-caffeoyl-beta-D-glucoside) 5-O-beta-D-glucoside
CoA + 4'''-demalonylsalvianin
involved in the late stage of biosynthesis of salvianin
-
-
?
malonyl-CoA + pelargonidin 3-O-(6-caffeoyl-beta-D-glucoside) 5-O-beta-D-glucoside
CoA + 4'''-demalonylsalvianin
-
Ss5MaT1 catalyzes the regiospecific transfer of the malonyl group from malonyl-CoA to the 6'''-hydroxyl group of the 5-glucosyl moiety of anthocyanins, e.g. bisdemalonylsalvianin, the presence of an aromatic acyl group at the 3-glucosidic moiety of anthocyanin is important for substrate recognition, strong acyl donor preference for malonyl-CoA
-
-
?
malonyl-CoA + pelargonidin 3-O-(6-caffeoyl-beta-D-glucoside) 5-O-beta-D-glucoside
CoA + 4'''-demalonylsalvianin
Ss5MaT1 catalyzes the regiospecific transfer of the malonyl group from malonyl-CoA to the 6'''-hydroxyl group of the 5-glycosyl moiety of anthocyanins, mechanism, both substrates and Ss5MaT1 form a complex before catalysis can occur, His-167, Asp-390 and Asn-315 are very important for catalytic activity, His-167 and Asp-390 appear to be involved in the general acid/base mechanism
-
-
?
additional information
?
-
-
Ss5MaT1 expression is temporally regulated during the color development of the flower, Ss5MaT1 plays a role during the coloration of the flowers, salvianin biosynthesis
-
-
-
additional information
?
-
-
not: 4'''-monodemalonylsalvianin, salvianin, pelargonidin 3,5-diglucoside, delphinidin 3,5-diglucoside, caffeoyl-CoA, p-coumaroyl-CoA, the second malonylation of 4'''-demalonylsalvianin to salvianin is catalyzed by a distinct malonyltransferase
-
-
-
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
malonyl-CoA + cyanidin 3-O-[[2-O-(2-O-sinapoyl)-beta-D-xylosyl]-6-O-(6-O-(4-coumaroyl)-beta-D-glucoside)] 5-O-beta-D-glucoside
CoA + cyanidin 3-O-[[2-O-(2-O-sinapoyl)-beta-D-xylosyl]-6-O-(6-O-(4-coumaroyl)-beta-D-glucoside)] 5-O-(6-O-malonyl)-beta-D-glucoside
Q9LJB4
-
-
-
?
malonyl-CoA + cyanidin 3-O-[[2-O-beta-D-xylosyl]-6-O-(6-O-(4-coumaroyl)-beta-D-glucoside)] 5-O-beta-D-glucoside
CoA + cyanidin 3-O-[[2-O-beta-D-xylosyl]-6-O-(6-O-(4-coumaroyl)-beta-D-glucoside)] 5-O-(6-O-malonyl)-beta-D-glucoside
Q9LJB4
-
-
-
?
malonyl-CoA + cyanin
CoA + cyanidin 3-O-beta-D-glucoside 5-O-(6-O-malonyl)-beta-D-glucoside
Q9LJB4
-
-
-
?
malonyl-CoA + malvin
CoA + malvidin 3-O-beta-D-glucoside 5-O-(6-O-malonyl)-beta-D-glucoside
Q9LJB4
-
-
-
?
malonyl-CoA + pelargonidin 3-O-(6-caffeoyl-beta-D-glucoside) 5-O-beta-D-glucoside
CoA + 4'''-demalonylsalvianin
Q8W1W9
involved in the late stage of biosynthesis of salvianin
-
-
?
additional information
?
-
-
Ss5MaT1 expression is temporally regulated during the color development of the flower, Ss5MaT1 plays a role during the coloration of the flowers, salvianin biosynthesis
-
-
-
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
CoA-SH
-
product inhibition, competitive versus malonyl-CoA, noncompetitive versus shisonin
malonylshisonin
-
product inhibition, noncompetitive versus shisonin and malonyl-CoA
additional information
-
not inhibited by Ca2+, Cd2+, Co2+, Fe2+, Mg2+, Mn2+, Ni2+, Sn2+, Zn2+, all at 0.1 mM, 1 mM dithiothreitol, 1 mM EDTA, 1% Tween 20, 1% Triton X-100, 0.1% CHAPS, 0.1 mM pelargonidin 3,5-diglucoside, 10 mM glucose
-
p-coumaric acid
-
dead-end inhibitor, competitive with respect to shisonin, uncompetitive with respect to malonyl-CoA
p-coumaric acid
-
competitive inhibitor with respect to shisonin, 10 mM, complete inhibition
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0076
cyanidin 3-O-[[2-O-(2-O-sinapoyl)-beta-D-xylosyl]-6-O-(6-O-(4-coumaroyl)-beta-D-glucoside)] 5-O-beta-D-glucoside
pH 7.1, 25°C
0.07
cyanidin 3-O-[[2-O-beta-D-xylosyl]-6-O-(6-O-(4-coumaroyl)-beta-D-glucoside)] 5-O-beta-D-glucoside
pH 7.1, 25°C
0.101
pelargonidin 3-O-(6-caffeoyl-beta-D-glucoside) 5-O-beta-D-glucoside
-
pH 7, 30°C, malonyl-CoA as cosubstrate
additional information
additional information
-
effects of pH on kinetic parameters, kinetic mechanism
-
0.0021
malonyl-CoA
cyanidin 3-O-[[2-O-(2-O-sinapoyl)-beta-D-xylosyl]-6-O-(6-O-(4-coumaroyl)-beta-D-glucoside)] 5-O-beta-D-glucoside as co-substrate, pH 7.1, 25°C
0.0064
malonyl-CoA
-
pH 7, 30°C, shisonin as cosubstrate, H167A mutant Ss5MaT1
0.013
malonyl-CoA
-
pH 7, 30°C, shisonin as cosubstrate, Y45A mutant Ss5MaT1
0.014
malonyl-CoA
-
pH 7, 30°C, shisonin as cosubstrate, Q150A mutant Ss5MaT1
0.0153
malonyl-CoA
cyanidin 3-O-[[2-O-beta-D-xylosyl]-6-O-(6-O-(4-coumaroyl)-beta-D-glucoside)] 5-O-beta-D-glucoside as co-substrate, pH 7.1, 25°C
0.02
malonyl-CoA
-
pH 7, 30°C, shisonin as cosubstrate, K258A mutant Ss5MaT1
0.0219
malonyl-CoA
-
pH 7, 30°C, shisonin as cosubstrate, recombinant Ss5MaT1
0.025
malonyl-CoA
-
pH 7, 30°C, shisonin as cosubstrate, N315A mutant Ss5MaT1
0.035
malonyl-CoA
-
pH 7, 30°C, shisonin as cosubstrate, R301A mutant Ss5MaT1
0.071
malonyl-CoA
-
pH 7, 30°C, shisonin as cosubstrate, D171A mutant Ss5MaT1
0.0054
shisonin
-
pH 7, 30°C, malonyl-CoA as cosubstrate, H167A mutant Ss5MaT1
0.019
shisonin
-
pH 7, 30°C, malonyl-CoA as cosubstrate, Y45A mutant Ss5MaT1
0.0355
shisonin
-
pH 7, 30°C, malonyl-CoA as cosubstrate, recombinant Ss5MaT1
0.039
shisonin
-
pH 7, 30°C, malonyl-CoA as cosubstrate, Q150A mutant Ss5MaT1
0.044
shisonin
-
pH 7, 30°C, malonyl-CoA as cosubstrate, K258A mutant Ss5MaT1
0.062
shisonin
-
pH 7, 30°C, malonyl-CoA as cosubstrate, N315A mutant Ss5MaT1
0.084
shisonin
-
pH 7, 30°C, malonyl-CoA as cosubstrate, R301A mutant Ss5MaT1
0.49
shisonin
-
pH 7, 30°C, malonyl-CoA as cosubstrate, D171A mutant Ss5MaT1
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00012
cyanidin 3-O-[[2-O-(2-O-sinapoyl)-beta-D-xylosyl]-6-O-(6-O-(4-coumaroyl)-beta-D-glucoside)] 5-O-beta-D-glucoside
pH 7.1, 25°C
0.12
cyanidin 3-O-[[2-O-beta-D-xylosyl]-6-O-(6-O-(4-coumaroyl)-beta-D-glucoside)] 5-O-beta-D-glucoside
pH 7.1, 25°C
7.8
pelargonidin 3-O-(6-caffeoyl-beta-D-glucoside) 5-O-beta-D-glucoside
-
pH 7, 30°C, malonyl-CoA as cosubstrate
0.0013
malonyl-CoA
cyanidin 3-O-[[2-O-(2-O-sinapoyl)-beta-D-xylosyl]-6-O-(6-O-(4-coumaroyl)-beta-D-glucoside)] 5-O-beta-D-glucoside as co-substrate, pH 7.1, 25°C
0.2
malonyl-CoA
cyanidin 3-O-[[2-O-beta-D-xylosyl]-6-O-(6-O-(4-coumaroyl)-beta-D-glucoside)] 5-O-beta-D-glucoside as co-substrate, pH 7.1, 25°C
0.001
shisonin
-
below, pH 7, 30°C, malonyl-CoA as cosubstrate, D390A mutant Ss5MaT1
0.002
shisonin
-
pH 7, 30°C, malonyl-CoA as cosubstrate, H167A mutant Ss5MaT1
0.072
shisonin
-
pH 7, 30°C, malonyl-CoA as cosubstrate, D171A mutant Ss5MaT1
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.016
cyanidin 3-O-[[2-O-(2-O-sinapoyl)-beta-D-xylosyl]-6-O-(6-O-(4-coumaroyl)-beta-D-glucoside)] 5-O-beta-D-glucoside
pH 7.1, 25°C
1.71
cyanidin 3-O-[[2-O-beta-D-xylosyl]-6-O-(6-O-(4-coumaroyl)-beta-D-glucoside)] 5-O-beta-D-glucoside
pH 7.1, 25°C
0.62
malonyl-CoA
cyanidin 3-O-[[2-O-(2-O-sinapoyl)-beta-D-xylosyl]-6-O-(6-O-(4-coumaroyl)-beta-D-glucoside)] 5-O-beta-D-glucoside as co-substrate, pH 7.1, 25°C
13.1
malonyl-CoA
cyanidin 3-O-[[2-O-beta-D-xylosyl]-6-O-(6-O-(4-coumaroyl)-beta-D-glucoside)] 5-O-beta-D-glucoside as co-substrate, pH 7.1, 25°C
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
Ss5MaT1 mRNA is mainly accumulated in young to opening petals and sepals
-
Ss5MaT1 mRNA is mainly accumulated in young to opening petals and sepals
-
red stems, Ss5MaT1 mRNA is present at a lower level than in petals and sepals
-
recently opened flowers, less than 2 cm in length, Ss5MaT1 mRNA is mainly accumulated in young to opening petals and sepals
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
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OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
into the entry vector pDONR207, the entry clone is used to transfer the open reading frame into the expression plasmid pH9GW for expression of the protein in Escherichia coli Bl21DE3 cells
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
agriculture
-
Ss5MaT1 cDNA may be an important tool for controlling flower colors by metabolic engineering of anthocyanin biosynthesis
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LINKS TO OTHER DATABASES (specific for EC-Number 2.3.1.172)
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