Information on EC 2.4.1.116 - cyanidin 3-O-rutinoside 5-O-glucosyltransferase

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The expected taxonomic range for this enzyme is: Gunneridae

EC NUMBER
COMMENTARY hide
2.4.1.116
-
RECOMMENDED NAME
GeneOntology No.
cyanidin 3-O-rutinoside 5-O-glucosyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
UDP-alpha-D-glucose + cyanidin-3-O-rutinoside = UDP + cyanidin 3-O-rutinoside 5-O-beta-D-glucoside
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hexosyl group transfer
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-
-
-
transfer of glycosyl group
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Anthocyanin biosynthesis
-
-
pelargonidin conjugates biosynthesis
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-
SYSTEMATIC NAME
IUBMB Comments
UDP-alpha-D-glucose:cyanidin-3-O-alpha-L-rhamnosyl-(1->6)-beta-D-glucoside 5-O-beta-D-glucosyltransferase
Isolated from the plants Silene dioica (red campion) [1], Iris ensata (Japanese iris) [2] and Iris hollandica (Dutch iris) [3]. Also acts on the 3-O-rutinosides of pelargonidin, delphinidin and malvidin, but not the corresponding glucosides or 6-acylglucosides. The enzyme does not catalyse the glucosylation of the 5-hydroxy group of cyanidin 3-glucoside.
CAS REGISTRY NUMBER
COMMENTARY hide
70248-66-7
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
enzyme has activity of both EC 2.4.1.115 and EC 2.4.1.116
-
-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
anthocyanidin + UDP-D-glucose
anthocyanidin 5-O-glucoside + UDP
show the reaction diagram
-
-
-
-
?
anthocyanidin 5-O-glucoside + UDP-D-glucose
anthocyanidin-3,5-O-diglucoside + UDP
show the reaction diagram
-
-
-
-
?
UDP-alpha-D-glucose + pelargonidin 3-O-(6-O-alpha-L-rhamnosyl)-beta-D-glucoside
UDP + pelargonidin 3-O-(6-O-alpha-L-rhamnosyl)-beta-D-glucosyl-5-O-beta-D-glucoside
show the reaction diagram
-
-
-
?
UDP-glucose + anthocyanidin-3-O-glucoside
UDP + anthocyanidin-3,5-O-diglucoside
show the reaction diagram
-
at pH 6.5, but not at pH 7.4, substrate specificity is pH-dependent
-
-
?
UDP-glucose + anthocyanidin-3-O-rutinoside
UDP + anthocyanidin-3-O-rutinoside 5-O-beta-D-glucoside
show the reaction diagram
-
at pH 7.4, substrate specificity is pH-dependent
-
-
?
UDP-glucose + cyanidin-3-O-glucoside
UDP + cyanidin-3,5-diglucoside
show the reaction diagram
UDP-glucose + cyanidin-3-O-rutinoside
UDP + cyanidin 3-O-rutinoside-5-O-beta-D-glucoside
show the reaction diagram
-
biosynthetic pathway of cyanidin-3-rhamnosylglucoside-5-glucoside, enzyme activity is controlled by a single dominant gene M
-
-
?
UDP-glucose + cyanidin-3-O-rutinoside
UDP + cyanidin-3-O-rutinoside-5-O-beta-D-glucoside
show the reaction diagram
-
catalyzes the transfer of the glucosyl moiety of UDP-glucose to the 5-hydroxyl group of cyanidin-3-rhamnosyl-(1?6)-glucoside
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-
?
UDP-glucose + pelargonidin-3-rutinoside
UDP + pelargonidin-3-rutinoside-5-O-beta-D-glucoside
show the reaction diagram
-
also uses pelargonidin-3-rhamnosylglucoside, glucosylates the 5-hydroxyl group
-
-
?
UDPglucose + cyanidin 3-O-D-glucoside
UDP + ?
show the reaction diagram
-
-
depending upon pH, the enzyme catalyzes the formation of either anthocyanidin 3-rhamnosylglucoside or 3,5-diglucoside. Maximal formation of anthocyanidin 3-rhamnosylglucoside-5-gluside at pH 7.4, maximal formation of anthocyanidin 3,5-diglucoside at pH 6.5. Formation of cyanidin 3-rhamnosylglucoside-5-glucoside proceeds 5-10fold faster than the cyanidin 3,5-diglucoside formation
?
UDPglucose + cyanidin 3-O-D-rhamnosylglucoside
UDP + ?
show the reaction diagram
-
-
depending upon pH, the enzyme catalyzes the formation of either anthocyanidin 3-rhamnosylglucoside or 3,5-diglucoside. Maximal formation of anthocyanidin 3-rhamnosylglucoside-5-gluside at pH 7.4, maximal formation of anthocyanidin 3,5-diglucoside at pH 6.5
?
UDPglucose + cyanidin-3-O-D-rhamnosyl-1,6-D-glucoside
UDP + cyanidin-3-O-[D-rhamnosyl-1,6-D-glucoside]-5-O-D-glucoside
show the reaction diagram
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
UDP-glucose + cyanidin-3-O-rutinoside
UDP + cyanidin 3-O-rutinoside-5-O-beta-D-glucoside
show the reaction diagram
-
biosynthetic pathway of cyanidin-3-rhamnosylglucoside-5-glucoside, enzyme activity is controlled by a single dominant gene M
-
-
?
UDPglucose + cyanidin-3-O-D-rhamnosyl-1,6-D-glucoside
UDP + cyanidin-3-O-[D-rhamnosyl-1,6-D-glucoside]-5-O-D-glucoside
show the reaction diagram
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involved in anthocyan biosynthesis. Activity is controlled by a single dominant gene
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Co2+
-
1 mM, stimulation
Mg2+
-
1 mM, stimulation
Mn2+
-
1 mM, stimulation
additional information
-
enzyme is stimulated by divalent metal ions
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
HgCl2
-
0.1 mM, 95% inhibition, irreversible inhibition
N-ethylmaleimide
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3 mM, 25% inhibition
NEM
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3 mM, 25% inhibition, 2-mercpatoethanol or cysteine does not protect
p-chloromercuribenzoate
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3 mM, 25% inhibition
PCMB
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3 mM, 25% inhibition, 2-mercpatoethanol or cysteine does not protect
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Co2+
-
1 mM activates
Mg2+
-
1 mM activates
Mn2+
-
1 mM activates
Polyvinylpyrrolidone
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soluble, required for maximal activity in crude extracts
additional information
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2 - 3.4
anthocyanidin-3-O-glucoside
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pH 6.5
3.6
anthocyanidin-3-O-rutinoside
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pH 7.4
23.4
cyanidin-3-glucoside
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-
3.6
cyanidin-3-O-rutinoside
0.5 - 0.6
UDP-glucose
0.59 - 0.67
UDPglucose
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.00953
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; pH 7.4, 30C
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6 - 7.3
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pH 6.0: about 80% of maximal activity, pH 7.3: about 50% of half-maximal activity, reaction with cyanidin 3-glucoside
6.9 - 8.8
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about 50% of maximal activity at pH 6.9 and at pH 8.8; half-maximum velocities at pH 6.9 and 8.8, cyanidin-3-O-rutinoside as substrate
7 - 8.5
-
about half-maximal activity at pH 7 and 8.5, reaction with cyanidin-3-rhamnosylglucoside
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
additional information
-
not in green parts of the plant
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
55000
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gel filtration
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.6
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30 min, stable below
488479
8
-
30 min, about 10% loss of activity
488479
8.5
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30 min, about 40% loss of activity
488479
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
repeated freeze-thawing inactivates
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repeated freezing and thawing leads to a rapid decline in activity
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, about 60-80% loss of activity within 3 months
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-20C, concentrated enzyme preparation, 3 months, 60-80% loss of activity
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
79.4fold; partial
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