Information on EC 2.3.1.172 - anthocyanin 5-O-glucoside 6'''-O-malonyltransferase

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)

The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.3.1.172
-
RECOMMENDED NAME
GeneOntology No.
anthocyanin 5-O-glucoside 6'''-O-malonyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
malonyl-CoA + pelargonidin 3-O-(6-caffeoyl-beta-D-glucoside) 5-O-beta-D-glucoside = CoA + 4'''-demalonylsalvianin
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malonylation
transfer of acyl group
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Anthocyanin biosynthesis
-
-
salvianin biosynthesis
-
-
shisonin biosynthesis
-
-
superpathway of anthocyanin biosynthesis (from cyanidin and cyanidin 3-O-glucoside)
-
-
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.
CAS REGISTRY NUMBER
COMMENTARY hide
380229-66-3
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
SwissProt
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
acetyl-CoA + shisonin
CoA + acetylshisonin
show the reaction diagram
-
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
show the reaction diagram
-
-
-
?
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
show the reaction diagram
-
-
-
?
malonyl-CoA + cyanin
CoA + cyanidin 3-O-beta-D-glucoside 5-O-(6-O-malonyl)-beta-D-glucoside
show the reaction diagram
-
-
-
?
malonyl-CoA + malvin
CoA + malvidin 3-O-beta-D-glucoside 5-O-(6-O-malonyl)-beta-D-glucoside
show the reaction diagram
-
-
-
?
malonyl-CoA + pelargonidin 3-O-(6-caffeoyl-beta-D-glucoside) 5-O-beta-D-glucoside
CoA + 4'''-demalonylsalvianin
show the reaction diagram
malonyl-CoA + shisonin
CoA + 6'''-malonylshisonin
show the reaction diagram
-
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
show the reaction diagram
Ss5MaT1 specifically catalyzes the malonylation of the 6'''-hydroxyl group of the 5-glucosyl moiety
-
-
?
methylmalonyl-CoA + shisonin
CoA + methylmalonylshisonin
show the reaction diagram
-
3% of the activity with malonyl-CoA as acyl donor
-
-
?
succinyl-CoA + shisonin
CoA + succinylshisonin
show the reaction diagram
-
49% of the activity with malonyl-CoA as acyl donor
-
-
?
additional information
?
-
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 + 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
show the reaction diagram
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
show the reaction diagram
Q9LJB4
-
-
-
?
malonyl-CoA + cyanin
CoA + cyanidin 3-O-beta-D-glucoside 5-O-(6-O-malonyl)-beta-D-glucoside
show the reaction diagram
Q9LJB4
-
-
-
?
malonyl-CoA + malvin
CoA + malvidin 3-O-beta-D-glucoside 5-O-(6-O-malonyl)-beta-D-glucoside
show the reaction diagram
Q9LJB4
-
-
-
?
malonyl-CoA + pelargonidin 3-O-(6-caffeoyl-beta-D-glucoside) 5-O-beta-D-glucoside
CoA + 4'''-demalonylsalvianin
show the reaction diagram
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
-
-
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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
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
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
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
0.167
cyanin
pH 7.1, 25°C
0.0021 - 0.071
malonyl-CoA
2.26
malvin
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
0.0054 - 0.49
shisonin
additional information
additional information
-
effects of pH on kinetic parameters, kinetic mechanism
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
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
Arabidopsis thaliana
Q9LJB4
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
Arabidopsis thaliana
Q9LJB4
pH 7.1, 25°C
0.02
cyanin
Arabidopsis thaliana
Q9LJB4
pH 7.1, 25°C
0.0013 - 0.2
malonyl-CoA
1.79
malvin
Arabidopsis thaliana
Q9LJB4
pH 7.1, 25°C
7.8
pelargonidin 3-O-(6-caffeoyl-beta-D-glucoside) 5-O-beta-D-glucoside
Salvia splendens
-
pH 7, 30°C, malonyl-CoA as cosubstrate
0.001 - 8.7
shisonin
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
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
Arabidopsis thaliana
Q9LJB4
pH 7.1, 25°C
42640
1.71
cyanidin 3-O-[[2-O-beta-D-xylosyl]-6-O-(6-O-(4-coumaroyl)-beta-D-glucoside)] 5-O-beta-D-glucoside
Arabidopsis thaliana
Q9LJB4
pH 7.1, 25°C
42639
0.12
cyanin
Arabidopsis thaliana
Q9LJB4
pH 7.1, 25°C
18588
0.62 - 13.1
malonyl-CoA
76
0.79
malvin
Arabidopsis thaliana
Q9LJB4
pH 7.1, 25°C
18589
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.17
-
pH 7, 30°C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7
-
assay at
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 11
-
active in the range
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
Ss5MaT1 mRNA is present at a lower level than in petals and sepals
Manually annotated by BRENDA team
-
Ss5MaT1 mRNA is mainly accumulated in young to opening petals and sepals
Manually annotated by BRENDA team
-
Ss5MaT1 mRNA is mainly accumulated in young to opening petals and sepals
Manually annotated by BRENDA team
-
red stems, Ss5MaT1 mRNA is present at a lower level than in petals and sepals
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
presumably located in
Manually annotated by BRENDA team
-
recombinant Ss5MaT1
-
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
46000
-
gel filtration
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
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
-
1 * 50000, SDS-PAGE, 1 * 50723, sequence calculation
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5
-
20°C, 20 h, stable
656032
8.5
-
unstable above
654691
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
-
pH 7, 20 min, stable below 30°C
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
2-mercaptoethanol stabilizes during purification
-
OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
extremely unstable to oxidation
-
656032
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
native Ss5MaT1 from flowers: 685fold, recombinant Ss5MaT1
-
using His-tag affinity chromatography
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
D171A
-
kinetic parameters, mutant with severely reduced activity
D390A
-
kinetic parameters
H167A
-
kinetic parameters, mutant with severely reduced activity
K258A
-
kinetic parameters
N315A
-
kinetic parameters, mutant with reduced activity
Q150A
-
kinetic parameters
R301A
-
kinetic parameters
Y45A
-
kinetic parameters
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
agriculture
-
Ss5MaT1 cDNA may be an important tool for controlling flower colors by metabolic engineering of anthocyanin biosynthesis