Information on EC 2.4.1.299 - cyanidin 3-O-glucoside 5-O-glucosyltransferase (acyl-glucose)

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The expected taxonomic range for this enzyme is: Dianthus caryophyllus

EC NUMBER
COMMENTARY hide
2.4.1.299
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RECOMMENDED NAME
GeneOntology No.
cyanidin 3-O-glucoside 5-O-glucosyltransferase (acyl-glucose)
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
1-O-sinapoyl-beta-D-glucose + cyanidin 3-O-beta-D-glucoside = sinapate + cyanidin 3,5-di-O-beta-D-glucoside
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Anthocyanin biosynthesis
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cyanidin diglucoside biosynthesis (acyl-glucose dependent)
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delphinidin diglucoside biosynthesis (acyl-glucose dependent)
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pelargonidin diglucoside biosynthesis (acyl-glucose dependent)
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SYSTEMATIC NAME
IUBMB Comments
1-O-sinapoyl-beta-D-glucose:cyanidin-3-O-beta-D-glucoside 5-O-beta-D-glucosyltransferase
Isolated from the plant Dianthus caryophyllus (carnation). Also acts on other anthocyanidins and with other acyl-glucose donors. cf. EC 2.4.1.298, anthocyanidin 3-O-glucoside 5-O-glucosyltransferase.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
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the enzyme belongs to the glycoside hydrolase family 1, molecular phylogenetic tree based on amino acid sequences, overview
physiological function
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in carnation petals, an acyl-glucose, 1-O-beta-D-vanillyl-glucose, acts as the donor molecule in the glucosyl transfer reaction at the 5 position of anthocyanin
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
1-O-4-coumaroyl-beta-D-glucose + cyanidin 3-O-beta-D-glucoside
4-coumarate + cyanidin 3,5-di-O-beta-D-glucoside
show the reaction diagram
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-
-
-
?
1-O-4-hydroxybenzoyl-beta-D-glucose + cyanidin 3-O-beta-D-glucoside
4-hydroxybenzoate + cyanidin 3,5-di-O-beta-D-glucoside
show the reaction diagram
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-
-
-
?
1-O-caffeoyl-beta-D-glucose + cyanidin 3-O-beta-D-glucoside
caffeate + cyanidin 3,5-di-O-beta-D-glucoside
show the reaction diagram
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-
-
-
?
1-O-feruloyl-beta-D-glucose + cyanidin 3-O-beta-D-glucoside
ferulate + cyanidin 3,5-di-O-beta-D-glucoside
show the reaction diagram
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1-O-feruloyl-beta-D-glucose is the best donor substrate
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-
?
1-O-isovanilloyl-beta-D-glucose + cyanidin 3-O-beta-D-glucoside
isovanillate + cyanidin 3,5-di-O-beta-D-glucoside
show the reaction diagram
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-
-
-
?
1-O-sinapoyl-beta-D-glucose + cyanidin 3-O-beta-D-glucoside
sinapate + cyanidin 3,5-di-O-beta-D-glucoside
show the reaction diagram
-
-
-
-
?
1-O-vanilloyl-beta-D-glucose + cyanidin 3-O-(6-O-malyl)beta-D-glucoside
vanillate + cyanidin 3-O-(6-O-malyl)beta-D-glucosyl-5-O-beta-D-glucoside
show the reaction diagram
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-
-
-
?
1-O-vanilloyl-beta-D-glucose + cyanidin 3-O-beta-D-galactoside
vanillate + cyanidin 3,5-di-O-beta-D-galactoside
show the reaction diagram
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-
-
-
?
1-O-vanilloyl-beta-D-glucose + cyanidin 3-O-beta-D-glucoside
vanillate + cyanidin 3,5-di-O-beta-D-glucoside
show the reaction diagram
1-O-vanilloyl-beta-D-glucose + delphinidin 3-O-beta-D-glucoside
vanillate + delphinidin 3,5-di-O-beta-D-glucoside
show the reaction diagram
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-
-
-
?
1-O-vanilloyl-beta-D-glucose + pelargonidin 3-O-(6-O-malyl)-beta-D-glucoside
vanillate + pelargonidin 3-O-(6-O-malyl)-beta-D-glucosyl-5-O-beta-D-glucoside
show the reaction diagram
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-
-
-
?
1-O-vanilloyl-beta-D-glucose + pelargonidin 3-O-beta-D-glucoside
vanillate + pelargonidin 3,5-di-O-beta-D-glucoside
show the reaction diagram
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-
-
-
?
additional information
?
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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
1-O-vanilloyl-beta-D-glucose + cyanidin 3-O-beta-D-glucoside
vanillate + cyanidin 3,5-di-O-beta-D-glucoside
show the reaction diagram
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-
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-
?
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0465 - 0.0519
1-O-vanilloyl-beta-D-glucose
0.0065 - 0.013
cyanidin 3-O-beta-D-glucoside
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.01
1-O-vanilloyl-beta-D-glucose
Dianthus caryophyllus
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pH 5.0, 30C, native and recombinant enzyme
0.06 - 0.07
cyanidin 3-O-beta-D-glucoside
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
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the enzyme expression is restricted to petals, no activity in leaves and stems, overview
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
55000
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x * 55000, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 55000, SDS-PAGE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
proteolytic modification
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the AA5GT contains 30 additional amino acids at the N terminus deleted in the mature protein
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
AA5GT protein from carnation petals
AB646511
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
AA5GT, DNA and amino acid sequence determination and analysis, expression analysis in different varieties
AB646511
transient expression as GFP-tagged protein in onion epidermal cells in vacuoles and cytosol using the CaMV 35S promoter
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