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

for references in articles please use BRENDA:EC2.3.1.153
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The enzyme appears in viruses and cellular organisms

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EC NUMBER
COMMENTARY hide
2.3.1.153
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RECOMMENDED NAME
GeneOntology No.
anthocyanin 5-(6'''-hydroxycinnamoyltransferase)
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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.
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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
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
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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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?
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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
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
PCMB
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90% inhibition at 0.1 mM, complete inhibition at 1 mM
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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
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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
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
49000
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gel filtration
49550
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SDS-PAGE
52000
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1 * 52000, SDS-PAGE
55350
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SDS-PAGE
57000
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His-tagged fusion protein, SDS-PAGE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
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1 * 52000, SDS-PAGE
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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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LINKS TO OTHER DATABASES (specific for EC-Number 2.3.1.153)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
InterPro (database of protein families, domains and functional sites)