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EC Tree
IUBMB Comments 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.
The enzyme appears in viruses and cellular organisms
Synonyms
ss5mat1, malonyl-coa:anthocyanin,
more
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5-O-glucoside-6'''-O-malonyltransferase
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anthocyanidin 5-glucoside malonyltransferase
-
anthocyanidin 5-glycoside malonyltransferase
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anthocyanin 5-glycoside malonyltransferase
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malonyl CoA:anthocyanidin 5-O-glucoside-6"-O-malonyltransferase
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malonyl-CoA:anthocyanin
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malonyl-CoA:anthocyanin 5-O-glucoside-6"'-O-malonyltransferase
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malonyl-CoA:anthocyanin 5-O-glucoside-6'''-O-malonyltransferase
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malonyltransferase, anthocyanidin 5-glycoside
-
additional information
member of the versatile plant acyltransferase family
additional information
member of the versatile plant acyltransferase family
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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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-
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malonylation
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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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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
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-
-
?
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
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-
-
?
malonyl-CoA + malvin
CoA + malvidin 3-O-beta-D-glucoside 5-O-(6-O-malonyl)-beta-D-glucoside
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-
-
?
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, enzyme catalyzes exclusively the monomalonylation of shisonin, strong acyl donor preference for malonyl-CoA
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-
?
malonyl-CoA + shisonin
CoA + malonylshisonin
Ss5MaT1 specifically catalyzes the malonylation of the 6'''-hydroxyl group of the 5-glucosyl moiety
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-
?
methylmalonyl-CoA + shisonin
CoA + methylmalonylshisonin
3% of the activity with malonyl-CoA as acyl donor
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-
?
succinyl-CoA + shisonin
CoA + succinylshisonin
49% of the activity with malonyl-CoA as acyl donor
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-
?
additional information
?
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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
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-
?
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
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-
?
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
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?
additional information
?
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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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?
additional information
?
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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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?
additional information
?
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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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-
?
additional information
?
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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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-
?
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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
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-
-
?
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
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?
malonyl-CoA + cyanin
CoA + cyanidin 3-O-beta-D-glucoside 5-O-(6-O-malonyl)-beta-D-glucoside
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-
-
?
malonyl-CoA + malvin
CoA + malvidin 3-O-beta-D-glucoside 5-O-(6-O-malonyl)-beta-D-glucoside
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-
?
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
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-
?
additional information
?
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additional information
?
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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
?
-
-
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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-
?
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acetyl-CoA
1 mM, 48% inhibition
caffeic acid
10 mM, complete inhibition
CoA-SH
product inhibition, competitive versus malonyl-CoA, noncompetitive versus shisonin
Cu2+
0.1 mM, complete inhibition
diethyldicarbonate
1 mM, 51% inhibition, 20 min, 20°C
Hg2+
0.1 mM, complete inhibition
malonylshisonin
product inhibition, noncompetitive versus shisonin and malonyl-CoA
N-ethylmaleimide
5 mM, 53% inhibition, 20 min, 20°C
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
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
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additional information
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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
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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
0.167
cyanin
pH 7.1, 25°C
0.0021 - 0.071
malonyl-CoA
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
-
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
0.0141
malonyl-CoA
pH 7, 30°C, shisonin as cosubstrate, native 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
0.022
malonyl-CoA
pH 7, 30°C, shisonin as cosubstrate, wild-type 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
0.057
malonyl-CoA
pH 7, 30°C, bisdemalonylsalvianin as cosubstrate
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
0.035
shisonin
pH 7, 30°C, malonyl-CoA as cosubstrate, wild-type 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
0.0402
shisonin
pH 7, 30°C, malonyl-CoA as cosubstrate, native 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
additional information
additional information
effects of pH on kinetic parameters, kinetic mechanism
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additional information
additional information
-
effects of pH on kinetic parameters, kinetic mechanism
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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
0.1
shisonin
pH 7, 30°C, malonyl-CoA as cosubstrate, N315A mutant Ss5MaT1
1
shisonin
pH 7, 30°C, malonyl-CoA as cosubstrate, Y45A mutant Ss5MaT1
1.4
shisonin
pH 7, 30°C, malonyl-CoA as cosubstrate, R301A mutant Ss5MaT1
4.3
shisonin
pH 7, 30°C, malonyl-CoA as cosubstrate, native Ss5MaT1
5.3
shisonin
pH 7, 30°C, malonyl-CoA as cosubstrate, K258A mutant Ss5MaT1
5.8
shisonin
pH 7, 30°C, malonyl-CoA as cosubstrate, Q150A mutant Ss5MaT1
8.7
shisonin
pH 7, 30°C, malonyl-CoA as cosubstrate, recombinant Ss5MaT1
8.7
shisonin
pH 7, 30°C, malonyl-CoA as cosubstrate, wild-type Ss5MaT1
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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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6 - 11
active in the range
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30
assay at
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UniProt
brenda
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SwissProt
brenda
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Ss5MaT1 mRNA is present at a lower level than in petals and sepals
brenda
Ss5MaT1 mRNA is mainly accumulated in young to opening petals and sepals
brenda
Ss5MaT1 mRNA is mainly accumulated in young to opening petals and sepals
brenda
red stems, Ss5MaT1 mRNA is present at a lower level than in petals and sepals
brenda
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brenda
recently opened flowers, less than 2 cm in length, Ss5MaT1 mRNA is mainly accumulated in young to opening petals and sepals
brenda
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presumably located in
brenda
recombinant Ss5MaT1
-
brenda
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5MAT1_SALSN
462
0
50724
Swiss-Prot
other Location (Reliability: 2 )
A0A2G9H7N1_9LAMI
212
0
23347
TrEMBL
other Location (Reliability: 2 )
A0A2G9HMU9_9LAMI
136
0
15595
TrEMBL
other Location (Reliability: 4 )
A0A396GTQ4_MEDTR
232
0
26407
TrEMBL
other Location (Reliability: 3 )
A0A396JG09_MEDTR
64
0
7033
TrEMBL
other Location (Reliability: 3 )
A0A396IFE9_MEDTR
147
0
15870
TrEMBL
other Location (Reliability: 3 )
5MAT_ARATH
449
0
49440
Swiss-Prot
-
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49550
predicted molecular mass
50000
1 * 50000, SDS-PAGE, 1 * 50723, sequence calculation
50723
1 * 50000, SDS-PAGE, 1 * 50723, sequence calculation
55350
predicted molecular mass of the fusion protein
57000
determined by SDS-PAGE, fusion protein, At5MAT His-tagged
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monomer
1 * 50000, SDS-PAGE, 1 * 50723, sequence calculation
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D171A
kinetic parameters, mutant with severely reduced activity
H167A
kinetic parameters, mutant with severely reduced activity
N315A
kinetic parameters, mutant with reduced activity
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7.5
20°C, 20 h, stable
656032
8.5
unstable above
654691
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30
pH 7, 20 min, stable below 30°C
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2-mercaptoethanol stabilizes during purification
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extremely unstable to oxidation
656032
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native Ss5MaT1 from flowers: 685fold, recombinant Ss5MaT1
using His-tag affinity chromatography
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expression of wild-type and mutant Ss5MaT1 in Escherichia coli
from petals, expression in Escherichia coli JM109, sequencing
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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agriculture
Ss5MaT1 cDNA may be an important tool for controlling flower colors by metabolic engineering of anthocyanin biosynthesis
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Suzuki, H.; Nakayama, T.; Nishino, T.
Proposed mechanism and functional amino acid residues of malonyl-CoA:anthocyanin 5-O-glucoside-6'''-O-malonyltransferase from flowers of Salvia splendens, a member of the versatile plant acyltransferase family
Biochemistry
42
1764-1771
2003
Salvia splendens (Q8W1W9), Salvia splendens
brenda
Suzuki, H.; Nakayama, T.; Yonekura-Sakakibara, K.; Fukui, Y.; Nakamura, N.; Nakao, M.; Tanaka, Y.; Yamaguchi, M.A.; Kusumi, T.; Nishino, T.
Malonyl-CoA:anthocyanin 5-O-glucoside-6"'-O-malonyltransferase from scarlet sage (Salvia splendens) flowers. Enzyme purification, gene cloning, expression, and characterization
J. Biol. Chem.
276
49013-49019
2001
Salvia splendens (Q8W1W9), Salvia splendens
brenda
DAuria, J.C.; Reichelt, M.; Luck, K.; Svatos, A.; Gershenzon, J.
Identification and characterization of the BAHD acyltransferase malonyl CoA: anthocyanidin 5-O-glucoside-6-O-malonyltransferase (At5MAT) in Arabidopsis thaliana
FEBS Lett.
581
872-878
2007
Arabidopsis thaliana (Q9LJB4)
brenda
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