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Information on EC 2.3.1.215 - anthocyanidin 3-O-glucoside 6''-O-acyltransferase
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EC Tree
2.3.1.215 anthocyanidin 3-O-glucoside 6''-O-acyltransferaseIUBMB Comments
Isolated from the plants Perilla frutescens and Gentiana triflora (clustered gentian). Acts on a range of anthocyanidin 3-O-glucosides, 3,5-di-O-glucosides and cyanidin 3-rutinoside. It did not act on delphinidin 3,3',7-tri-O-glucoside. Recombinant Perilla frutescens enzyme could utilize caffeoyl-CoA but not malonyl-CoA as alternative acyl donor.
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The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
3AT, anthocyanidin 3-O-glucoside 6''-O-acyltransferase, anthocyanin 3-aromatic acyltransferase, hydroxycinnamoyl-CoA: anthocyanin 3-0-glucoside-6"-0-acyltransferase, hydroxycinnamoyl-CoA:anthocyanin 3-O-glucoside-6''-O-hydroxycinnamoyltransferase, Ih3AT1, Ih3AT2, VIT_03s0017g00870, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
3AT
hydroxycinnamoyl-CoA: anthocyanin 3-0-glucoside-6"-0-acyltransferase
-
hydroxycinnamoyl-CoA:anthocyanin 3-O-glucoside-6''-O-hydroxycinnamoyltransferase
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
4-hydroxycinnamoyl-CoA + an anthocyanidin 3-O-beta-D-glucoside = CoA + an anthocyanidin 3-O-[6-O-(4-hydroxycinnamoyl)-beta-D-glucoside]
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
4-hydroxycinnamoyl-CoA:anthocyanin-3-O-glucoside 6''-O-acyltransferase
Isolated from the plants Perilla frutescens and Gentiana triflora (clustered gentian). Acts on a range of anthocyanidin 3-O-glucosides, 3,5-di-O-glucosides and cyanidin 3-rutinoside. It did not act on delphinidin 3,3',7-tri-O-glucoside. Recombinant Perilla frutescens enzyme could utilize caffeoyl-CoA but not malonyl-CoA as alternative acyl donor.
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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
4-hydroxycinnamoyl-CoA + cyanidin 3,5-O-beta-D-diglucoside
CoA + cyanidin 3-O-[6-O-(4-hydroxycinnamoyl)-beta-D-glucosyl]-5-O-beta-D-glucoside
-
-
-
?
4-hydroxycinnamoyl-CoA + cyanidin 3-O-beta-D-glucoside
CoA + cyanidin 3-O-[6-O-(4-hydroxycinnamoyl)-beta-D-glucoside]
-
-
-
?
4-hydroxycinnamoyl-CoA + delphinidin 3,5-O-beta-D-diglucoside
CoA + delphinidin 3-O-(4-coumaroyl)-beta-D-glucoside-5-O-beta-D-glucoside
-
-
-
?
4-hydroxycinnamoyl-CoA + delphinidin 3-O-beta-D-glucoside
CoA + ?
-
-
-
-
?
4-hydroxycinnamoyl-CoA + delphinidin 3-O-beta-D-glucoside
CoA + delphinidin 3-O-[6-O-(4-hydroxycinnamoyl)-beta-D-glucoside]
-
-
-
?
4-hydroxycinnamoyl-CoA + pelargonidin 3,5-O-beta-D-diglucoside
CoA + pelargonidin 3-O-[6-O-(4-hydroxycinnamoyl)-beta-D-glucosyl]-5-O-beta-D-glucoside
-
-
-
?
4-hydroxycinnamoyl-CoA + pelargonidin 3-O-beta-D-glucoside
CoA + ?
-
-
-
-
?
4-hydroxycinnamoyl-CoA + pelargonidin 3-O-beta-D-glucoside
CoA + pelargonidin 3-O-[6-O-(4-hydroxycinnamoyl)-beta-D-glucoside]
-
-
-
?
anthocyanidin 3-rhamnosylglucoside-5-glucoside + p-coumaroyl-CoA
CoA + anthocyanidin 3-(p-coumaroyl)rhamnosylglucoside-5-glucoside
-
-
-
-
?
caffeoyl-CoA + cyanidin 3,5-O-beta-D-diglucoside
CoA + cyanidin 3-O-[6-O-caffeoyl-beta-D-glucosyl]-5-O-beta-D-glucoside
-
-
-
?
caffeoyl-CoA + cyanidin 3-O-beta-D-glucoside
CoA + cyanidin 3-O-[6-O-caffeoyl-beta-D-glucoside]
-
-
-
?
caffeoyl-CoA + delphinidin 3,5-O-beta-D-diglucoside
CoA + delphinidin 3,5-O-[6-O-caffeoyl-beta-D-diglucoside]
-
-
-
?
caffeoyl-CoA + delphinidin 3-O-beta-D-glucoside
CoA + delphinidin 3-O-[6-O-caffeoyl-beta-D-glucoside]
-
-
-
?
caffeoyl-CoA + pelargonidin 3,5-O-beta-D-diglucoside
CoA + pelargonidin 3-O-[6-O-caffeoyl-beta-D-glucoside]-5-O-beta-D-glucoside
-
-
-
?
caffeoyl-CoA + pelargonidin 3-O-beta-D-glucoside
CoA + pelargonidin 3-O-[6-O-caffeoyl-beta-D-glucoside]
-
-
-
?
cyanidin 3-O,5-O-beta-D-diglucoside + acetyl-CoA
CoA + cyanidin-3-O-(6-O-acetyl)-beta-D-glucosyl-5-O-beta-D-glucoside
-
-
-
?
cyanidin 3-O-beta-D-glucoside + acetyl-CoA
CoA + cyanidin 3-O-(6-O-acetyl)-beta-D-glucoside
-
-
-
?
delphinidin 3-O-beta-D-glucoside + acetyl-CoA
CoA + delphinidin 3-O-(6-O-acetyl)-beta-D-glucoside
-
-
-
?
delphinidin 3-rhamnosylglucoside-5-glucoside + p-coumaroyl-CoA
CoA + delphinidin 3-(p-coumaroyl)rhamnosylglucoside-5-glucoside
-
-
-
-
?
malvidin 3-O-beta-D-glucoside + acetyl-CoA
CoA + malvidin 3-O-(6-O-acetyl)-beta-D-glucoside
-
-
-
?
malvidin 3-O-beta-D-glucoside + caffeoyl-CoA
CoA + malvidin 3-O-(6-O-caffeoyl)-beta-D-glucoside
-
-
-
?
malvidin 3-O-beta-D-glucoside + coumaroyl-CoA
CoA + malvidin 3-O-(6-O-coumaroyl)-beta-D-glucoside
-
-
-
?
malvidin 3-O-beta-D-glucoside + malonyl-CoA
CoA + malvidin 3-O-(6-O-malonyl)-beta-D-glucoside
-
-
-
?
malvidin 3-rhamnosylglucoside-5-glucoside + p-coumaroyl-CoA
CoA + malvidin 3-(p-coumaroyl)rhamnosylglucoside-5-glucoside
-
-
-
-
?
peonidin 3-O-beta-D-glucoside + acetyl-CoA
CoA + peonidin 3-O-(6-O-acetyl)-beta-D-glucoside
-
-
-
?
petunidin 3-rhamnosylglucoside-5-glucoside + p-coumaroyl-CoA
CoA + petunidin 3-(p-coumaroyl)rhamnosylglucoside-5-glucoside
-
-
-
-
?
additional information
?
-
-
no substrate: delphinidin 3-glucoside, dephinidin 3-rhamnosylglucoside
-
-
?
additional information
?
-
-
lower Km values for anthocyanidin 3-O-beta-D-glucoside than 3,5-O-beta-D-diglucoside may indicate that acylation of cyanidin 3-O-beta-D-glucoside precedes 5-O-glucosylation in vivo
-
-
?
additional information
?
-
-
the enzyme catalyzes the transfer of the 4-coumaric and caffeic acids from their CoA esters to the 3-glucosyl moiety of delphinidin, cyanidin and pelargonidin 3-glucoside. Anthocyanidin 3,5-diglucosides are also good substrates, while cyanidin 3-rutinoside is a poor substrate. Malonyl-CoA is not used by the enzyme as an acyl-donor
-
-
?
additional information
?
-
the recombinant perilla 3AT protein has a broad substrate specificity for anthocyanins and recognizes anthocyanidin 3-glucosides, anthocyanidin 3,5-diglucosides and cyanidin 3-glucoside. Caffeoyl-CoA is preferred before 4-hydroxycinnamoyl-CoA. No activity with malonyl-CoA
-
-
?
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NATURAL SUBSTRATE
NATURAL 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
4-hydroxycinnamoyl-CoA + delphinidin 3-O-beta-D-glucoside
CoA + ?
-
-
-
-
?
4-hydroxycinnamoyl-CoA + pelargonidin 3-O-beta-D-glucoside
CoA + ?
-
-
-
-
?
additional information
?
-
-
lower Km values for anthocyanidin 3-O-beta-D-glucoside than 3,5-O-beta-D-diglucoside may indicate that acylation of cyanidin 3-O-beta-D-glucoside precedes 5-O-glucosylation in vivo
-
-
?
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
1.74
-
substrate delphinidin 3-rhamnosylglucoside-5-glucoside, pH 6.5, 35°C
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
red form, no expression in the green form, gene PfAT208
UniProt
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
PfAT208 transcript accumulation in the young leaves of the red, not of the green, form of perilla, overview
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
constitutive expression of 3AT in tobacco results in the production of acylated anthocyanins
additional information
-
red leaves accumulate cyanidin 3-(6-O-4-coumaroyl-beta-D-glucoside)-5-(6-O-malonyl-beta-D-glucoside)
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). 3AT_PERFR
446
0
50675
Swiss-Prot
other Location (Reliability: 3)
A0A396GP05_MEDTR
443
0
49785
TrEMBL
other Location (Reliability: 2)
A0A8K1JX13_ZINVI
461
0
51371
TrEMBL
other Location (Reliability: 1)
A0A396GWJ2_MEDTR
148
0
17046
TrEMBL
other Location (Reliability: 4)
A0A8K1JX20_ZINVI
451
0
50792
TrEMBL
other Location (Reliability: 1)
A0A8K1N837_ZINVI
466
0
51715
TrEMBL
other Location (Reliability: 4)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
47706
-
x * 47706, isoform Ih3AT1, x * 47760, isoform Ih3AT2, calculated, x * 50000, both isoforms, SDS-PAGE
47760
-
x * 47706, isoform Ih3AT1, x * 47760, isoform Ih3AT2, calculated, x * 50000, both isoforms, SDS-PAGE
50000
50000
-
x * 47706, isoform Ih3AT1, x * 47760, isoform Ih3AT2, calculated, x * 50000, both isoforms, SDS-PAGE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
-
x * 47706, isoform Ih3AT1, x * 47760, isoform Ih3AT2, calculated, x * 50000, both isoforms, SDS-PAGE
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
protein sequence changes and gene expression patterns of 3AT correlate with the absence of acylated anthocyanins in cv Pinot Noir and pale-fruited cv Cabernet Sauvignon mutants
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene PfAT208, DNA and amino acid sequence determination and analysis, sequence ccomparison, expression in Escherichia coli as fusion protein with beta-galactosidase
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
transcription factor MYBA is a positive regulator of the later stages of anthocyanin synthesis, modification, and transport in cv Shiraz. Anthocyanidin 3-O-glucoside 6''-O-acyltransferase is upregulated by MYBA
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Yoshihara, N.; Imayama, T.; Matsuo, Y.; Fukuchi-Mizutani, M.; Tanaka, Y.; Ino, I.; Yabuya, T.
Characterization of cDNA clones encoding anthocyanin 3-p-coumaroyltransferase from Iris hollandica
Plant Sci.
171
632-639
2006
Iris x hollandica
brenda
Fujiwara, H.; Tanaka, Y.; Fukui, Y.; Ashikari, T.; Yamaguchi, M.; Kusumi, T.
Purification and characterization of anthocyanin 3-aromatic acyltransferase from Perilla frutescens
Plant Sci.
137
87-94
1998
Perilla frutescens
-
brenda
Yonekura-Sakakibara, K.; Tanaka, Y.; Fukuchi-Mizutani, M.; Fujiwara, H.; Fukui, Y.; Ashikari, T.; Murakami, Y.; Yamaguchi, M.; Kusumi, T.
Molecular and biochemical characterization of a novel hydroxycinnamoyl-CoA:anthocyanin 3-O-glucoside-6-O-acyltransferase from Perilla frutescens
Plant Cell Physiol.
41
495-502
2000
Perilla frutescens (Q9MBC1)
brenda
Rinaldo, A.R.; Cavallini, E.; Jia, Y.; Moss, S.M.; McDavid, D.A.; Hooper, L.C.; Robinson, S.P.; Tornielli, G.B.; Zenoni, S.; Ford, C.M.; Boss, P.K.; Walker, A.R.
A grapevine anthocyanin acyltransferase, transcriptionally regulated by VvMYBA, can produce most acylated anthocyanins present in grape skins
Plant Physiol.
169
1897-1916
2015
Vitis vinifera (D7TU67)
brenda
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Release 2023.1 (January 2023)
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