Information on EC 2.3.1.153 - anthocyanin 5-(6'''-hydroxycinnamoyltransferase)

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.3.1.153
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RECOMMENDED NAME
GeneOntology No.
anthocyanin 5-(6'''-hydroxycinnamoyltransferase)
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
4-hydroxycinnamoyl-CoA + anthocyanidin 3,5-diglucoside = CoA + anthocyanidin 3-glucoside 5-(6-O-4-hydroxycinnamoylglucoside)
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Acyl group transfer
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
gentiodelphin biosynthesis
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Anthocyanin biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
4-hydroxycinnamoyl-CoA:anthocyanidin 3,5-diglucoside 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.
CAS REGISTRY NUMBER
COMMENTARY hide
179466-49-0
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182238-32-0
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198841-53-1
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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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Manually annotated by BRENDA team
white flower cultivar
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Manually annotated by BRENDA team
white flower cultivar
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Manually annotated by BRENDA team
white flower cultivar
UniProt
Manually annotated by BRENDA team
blue flower cultivar
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
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
show the reaction diagram
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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
show the reaction diagram
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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
show the reaction diagram
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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
show the reaction diagram
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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
show the reaction diagram
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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
show the reaction diagram
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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)
show the reaction diagram
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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
show the reaction diagram
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?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mn2+
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strongly enhances activity
Zn2+
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moderately enhances activity
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
PCMB
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90% inhibition at 0.1 mM, complete inhibition at 1 mM
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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
0.167
cyanin
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0.15
delphinidin 3,5-diglucoside
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with caffeoyl-CoA as cosubstrate
0.0021 - 0.0153
malonyl-CoA
2.26
malvin
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0.19
p-Coumaroyl-CoA
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with delphinidin 3,5-diglucoside as cosubstrate
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8 - 8.5
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 10
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active in this range
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
49000
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gel filtration
49550
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SDS-PAGE
55350
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SDS-PAGE
57000
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His-tagged fusion protein, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
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1 * 52000, SDS-PAGE
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-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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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
of the recombinant fusion protein using His-tag affinity chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression analysis
expression in Escherichia coli as His-tagged fusion protein
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