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EC Tree
IUBMB Comments Isolated from the plant Gentiana triflora. Transfers the hydroxycinnamoyl group only to the C-5 glucoside of anthocyanin. Caffeoyl-CoA, but not malonyl-CoA, can substitute as an acyl donor.
The enzyme appears in viruses and cellular organisms
Reaction Schemes
+
=
+
anthocyanidin 3-O-beta-D-glucoside 5-O-beta-D-(6-O-4-hydroxycinnamoylglucoside)
Synonyms
5AT, Acyltransferase, anthocyanin, Anthocyanidin 3,5-diglucoside 5-O-glucoside-6''-O-hydroxycinnamoyltransferase, anthocyanidin 5-O-glucoside-6''-O-malonyltransferase, anthocyanin 5-aromatic acyltransferase, Anthocyanin acyltransferase, Anthocyanin hydroxycinnamoyltransferase, Gentian 5AT, Hydroxycinnamoyl-CoA-anthocyanidin 3,5-diglucoside 5-O-glucoside-6'''-O-hydroxycinnamoyltransferase, Hydroxycinnamoyltransferase, anthocyanidin 3,5-diglucoside 5-O-glucoside-6''-O-,
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Acyltransferase, anthocyanin
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Anthocyanidin 3,5-diglucoside 5-O-glucoside-6''-O-hydroxycinnamoyltransferase
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anthocyanidin 5-O-glucoside-6''-O-malonyltransferase
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belongs to the BAHD acyltransferase malonyl CoA family
anthocyanin 5-aromatic acyltransferase
Anthocyanin acyltransferase
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Anthocyanin hydroxycinnamoyltransferase
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Hydroxycinnamoyl-CoA-anthocyanidin 3,5-diglucoside 5-O-glucoside-6'''-O-hydroxycinnamoyltransferase
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Hydroxycinnamoyltransferase, anthocyanidin 3,5-diglucoside 5-O-glucoside-6''-O-
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Hydroxycinnamoyltransferase, anthocyanin
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5AT
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anthocyanin 5-aromatic acyltransferase
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At5MAT
anthocyanin 5-aromatic acyltransferase
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anthocyanin 5-aromatic acyltransferase
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anthocyanin 5-aromatic acyltransferase
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anthocyanin 5-aromatic acyltransferase
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anthocyanin 5-aromatic acyltransferase
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4-hydroxycinnamoyl-CoA + an anthocyanidin 3,5-di-O-beta-D-glucoside = CoA + anthocyanidin 3-O-beta-D-glucoside 5-O-beta-D-(6-O-4-hydroxycinnamoylglucoside)
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Acyl group transfer
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4-hydroxycinnamoyl-CoA:anthocyanidin 3,5-di-O-beta-D-glucoside 5-O-glucoside-6'''-O-4-hydroxycinnamoyltransferase
Isolated from the plant Gentiana triflora. Transfers the hydroxycinnamoyl group only to the C-5 glucoside of anthocyanin. Caffeoyl-CoA, but not malonyl-CoA, can substitute as an acyl donor.
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2-(3,4-dihydroxyphenyl)-3-[[6-O-[(2E)-3-[4-(beta-D-glucopyranosyloxy)phenyl]prop-2-enoyl]-beta-D-glucopyranosyl-(1-6)-[2-O-[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]-beta-D-xylopyranosyl-(1-2)]-beta-D-glucopyranosyl]oxy]-7-hydroxychromenium-5-yl beta-D-glucopyranoside + malonyl-CoA
5-[[6-O-(carboxyacetyl)-beta-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-7-hydroxychromenium-3-yl 6-O-[(2E)-3-[4-(beta-D-glucopyranosyloxy)phenyl]prop-2-enoyl]-beta-D-glucopyranosyl-(1-6)-[2-O-[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]-beta-D-xylopyranosyl-(1-2)]-beta-D-glucopyranoside + CoA
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cyanindin A10
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?
2-(3,4-dihydroxyphenyl)-3-[[6-O-[(2E)-3-[4-(beta-D-glucopyranosyloxy)phenyl]prop-2-enoyl]-beta-D-glucopyranosyl-(1-6)-[beta-D-xylopyranosyl-(1-2)]-beta-D-glucopyranosyl]oxy]-7-hydroxychromenium-5-yl beta-D-glucopyranoside + malonyl-CoA
5-[[6-O-(carboxyacetyl)-beta-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-7-hydroxychromenium-3-yl 6-O-[(2E)-3-[4-(beta-D-glucopyranosyloxy)phenyl]prop-2-enoyl]-beta-D-glucopyranosyl-(1-6)-[beta-D-xylopyranosyl-(1-2)]-beta-D-glucopyranoside + CoA
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cyanindin A6, malonylation occurs exclusively on the 5-O-glucose
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?
cyanidin-3,5-O-beta-D-diglucoside + 4-coumaroyl-CoA
CoA + cyanidin 3-O-beta-D-glucoside-5-O-(6-O-4-coumaroyl)-beta-D-glucoside
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?
cyanidin-3,5-O-beta-D-diglucoside + caffeoyl-CoA
CoA + cyanidin 3-O-beta-D-glucoside-5-O-(6-O-caffeoyl)-beta-D-glucoside
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?
cyanin + malonyl-CoA
5-[[6-O-(carboxyacetyl)-b-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-7-hydroxychromenium-3-yl beta-D-glucopyranoside + CoA
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?
delphinidin 3,5-di-O-beta-D-glucoside + 4-coumaroyl-CoA
CoA + delphinidin 3-O-beta-D-glucoside-5-O-(6-O-4-coumaroyl)-beta-D-glucoside
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?
delphinidin 3,5-di-O-beta-D-glucoside + caffeoyl-CoA
CoA + delphinidin 3-O-beta-D-glucosyl-5-O-(6-O-caffeoyl-beta-D-glucoside)
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?
malvin + malonyl-CoA
5-[[6-O-(carboxyacetyl)-beta-D-glucopyranosyl]oxy]-7-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenium-3-yl beta-D-glucopyranoside + CoA
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?
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Mn2+
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strongly enhances activity
Zn2+
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moderately enhances activity
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PCMB
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90% inhibition at 0.1 mM, complete inhibition at 1 mM
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0.0076
2-(3,4-dihydroxyphenyl)-3-[[6-O-[(2E)-3-[4-(beta-D-glucopyranosyloxy)phenyl]prop-2-enoyl]-beta-D-glucopyranosyl-(1-6)-[2-O-[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]-beta-D-xylopyranosyl-(1-2)]-beta-D-glucopyranosyl]oxy]-7-hydroxychromenium-5-yl beta-D-glucopyranoside
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0.07
2-(3,4-dihydroxyphenyl)-3-[[6-O-[(2E)-3-[4-(beta-D-glucopyranosyloxy)phenyl]prop-2-enoyl]-beta-D-glucopyranosyl-(1-6)-[beta-D-xylopyranosyl-(1-2)]-beta-D-glucopyranosyl]oxy]-7-hydroxychromenium-5-yl beta-D-glucopyranoside
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0.065
caffeoyl-CoA
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with delphinidin 3,5-diglucoside as cosubstrate
0.087
cyanidin 3,5-diglucoside
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with caffeoyl-CoA as cosubstrate
0.15
delphinidin 3,5-diglucoside
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with caffeoyl-CoA as cosubstrate
0.0021 - 0.0153
malonyl-CoA
0.19
p-Coumaroyl-CoA
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with delphinidin 3,5-diglucoside as cosubstrate
0.0021
malonyl-CoA
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2-(3,4-dihydroxyphenyl)-3-[[6-O-[(2E)-3-[4-(beta-D-glucopyranosyloxy)phenyl]prop-2-enoyl]-beta-D-glucopyranosyl-(1-6)-[2-O-[(2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]-beta-D-xylopyranosyl-(1-2)]-beta-D-glucopyranosyl]oxy]-7-hydroxychromenium-5-yl beta-D-glucopyranoside as cosubstrate
0.0153
malonyl-CoA
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2-(3,4-dihydroxyphenyl)-3-[[6-O-[(2E)-3-[4-(beta-D-glucopyranosyloxy)phenyl]prop-2-enoyl]-beta-D-glucopyranosyl-(1-6)-[beta-D-xylopyranosyl-(1-2)]-beta-D-glucopyranosyl]oxy]-7-hydroxychromenium-5-yl beta-D-glucopyranoside as cosubstrate
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additional information
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5.5 - 10
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active in this range
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4-6-week-old rosette stage wild type, At3g29590, a mutant line incapable of producing malonylated anthocyanins and transgenic line harboring anRNAi silencing cassette for the enzyme
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brenda
white flower cultivar
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brenda
white flower cultivar
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brenda
white flower cultivar
UniProt
brenda
blue flower cultivar
UniProt
brenda
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UniProt
brenda
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brenda
blue flower cultivar
UniProt
brenda
white flower cultivar
UniProt
brenda
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skin
brenda
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bud stage and just before anthesis
brenda
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bud stage and just before anthesis
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brenda
bud stage and just before anthesis
brenda
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bud stage and just before anthesis
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brenda
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bud stage and just before anthesis
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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blue
brenda
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brenda
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brenda
additional information
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tissue expression analysis
brenda
additional information
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tissue expression analysis
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brenda
additional information
tissue expression analysis
brenda
additional information
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tissue expression analysis
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brenda
additional information
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tissue expression analysis
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brenda
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metabolism
overexpression of the acyltransferase gene Vv3AT increases the proportion of acylated anthocyanins in Malbec berries under high temperature
additional information
flavonoid accumulation in the blue- and white-flowered gentian cultivars, overview
additional information
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flavonoid accumulation in the blue- and white-flowered gentian cultivars, overview
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additional information
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flavonoid accumulation in the blue- and white-flowered gentian cultivars, overview
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ANTA_GENTR
469
0
52740
Swiss-Prot
other Location (Reliability: 2 )
B9RHE8_RICCO
464
0
51884
TrEMBL
other Location (Reliability: 5 )
B9SNQ3_RICCO
467
0
51663
TrEMBL
other Location (Reliability: 4 )
B9SNR0_RICCO
475
0
52850
TrEMBL
other Location (Reliability: 3 )
F4ZG54_MEDTR
468
0
53451
TrEMBL
other Location (Reliability: 3 )
B9SNQ1_RICCO
351
0
39081
TrEMBL
Mitochondrion (Reliability: 3 )
B9SNQ4_RICCO
474
0
53054
TrEMBL
other Location (Reliability: 2 )
B9RW82_RICCO
459
0
51645
TrEMBL
other Location (Reliability: 5 )
B9SNQ7_RICCO
458
0
50447
TrEMBL
other Location (Reliability: 2 )
B9SNQ9_RICCO
477
0
52949
TrEMBL
other Location (Reliability: 2 )
A0A2P6S7K6_ROSCH
489
0
54168
TrEMBL
Secretory Pathway (Reliability: 1 )
A0A438GF80_VITVI
261
0
29177
TrEMBL
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Q3V5Z1_GENTR
365
0
41194
TrEMBL
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52000
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1 * 52000, SDS-PAGE
57000
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His-tagged fusion protein, SDS-PAGE
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monomer
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1 * 52000, SDS-PAGE
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-20°C, 20 mM Tris/HCl, pH 7.0, 0.01 mM (p-aminidinophenyl)methanesulfonyl fluoride, 1 mM DTT, stable for at least 2 years
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of the recombinant fusion protein using His-tag affinity chromatography
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expression in Escherichia coli as His-tagged fusion protein
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expression analysis
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Fujiwara, H.; Tanaka, Y.; Fukui, Y.; Nakao, M.; Ashikari, T.; Kusumi, T.
Anthocyanin 5-aromatic acyltransferase from Gentiana triflora
Eur. J. Biochem.
249
45-51
1997
Gentiana triflora
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
brenda
Griesser, M.; Hoffmann, T.; Bellido, M.L.; Rosati, C.; Fink, B.; Kurtzer, R.; Aharoni, A.; Munoz-Blanco, J.; Schwab, W.
Redirection of flavonoid biosynthesis through the down-regulation of an anthocyanidin glucosyltransferase in ripening strawberry fruit
Plant Physiol.
146
1528-1539
2008
Gentiana scabra x Gentiana triflora, Gentiana triflora (Q3V5Z1), Gentiana triflora Homoi (Q3V5Z1), Gentiana scabra x Gentiana triflora Polano White, Gentiana triflora Maciry (Q3V5Z1)
brenda
de Rosas, I.; Ponce, M.T.; Malovini, E.; Deis, L.; Cavagnaro, B.; Cavagnaro, P.
Loss of anthocyanins and modification of the anthocyanin profiles in grape berries of Malbec and Bonarda grown under high temperature conditions
Plant Sci.
258
137-145
2017
Vitis vinifera (A0A438GF80), Vitis vinifera
brenda
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2.3.1.153 anthocyanin 5-(6'''-hydroxycinnamoyltransferase)
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