Information on EC 2.4.1.177 - cinnamate beta-D-glucosyltransferase

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.
Specify your search results
Select one or more organisms in this record:
Show additional data
Do not include text mining results
Include (text mining) results (more...)
Include results (AMENDA + additional results, but less precise; more...)

The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.4.1.177
-
RECOMMENDED NAME
GeneOntology No.
cinnamate beta-D-glucosyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
UDP-glucose + trans-cinnamate = UDP + trans-cinnamoyl beta-D-glucoside
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hexosyl group transfer
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
cinnamate esters biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
UDP-glucose:trans-cinnamate beta-D-glucosyltransferase
4-Coumarate, 2-coumarate, benzoate, feruloate and caffeate can also act as acceptors, but more slowly. Involved in the biosynthesis of chlorogenic acid in the root of the sweet potato, Ipomoea batatas.
CAS REGISTRY NUMBER
COMMENTARY hide
83744-95-0
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
expression in Escherichia coli
-
-
Manually annotated by BRENDA team
sweet potato, Lam cv. Norin 1
-
-
Manually annotated by BRENDA team
alfalfa, cv. Apollo
-
-
Manually annotated by BRENDA team
bean, cv. Canadian Wonder
-
-
Manually annotated by BRENDA team
Andr.
-
-
Manually annotated by BRENDA team
Verbesina caracasana
-
-
-
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
2,2-bis(4-chlorophenyl) acetic acid + UDP-glucose
?
show the reaction diagram
-
-
-
-
?
2,4,5-trichlorophenol + UDP-glucose
?
show the reaction diagram
-
225% of the activity with cinnamic acid
-
-
?
2,4-dichlorophenoxyacetic acid + UDP-glucose
?
show the reaction diagram
-
-
-
-
?
2,5-dimethyl-4-hydroxy-3[2H]-furanone + UDP-glucose
?
show the reaction diagram
-
-
-
-
?
3,4-dimethoxycinnamic acid + UDP-glucose
UDP + 3,4-dimethoxycinnamoyl-beta-D-glucoside
show the reaction diagram
-
-
-
-
3,5-dichloro-4-hydroxybenzoic acid + UDP-glucose
?
show the reaction diagram
-
102% of the activity with cinnamic acid
-
-
?
3-aminobenzoic acid + UDP-glucose
UDP + 3-aminobenzoyl-beta-D-glucoside
show the reaction diagram
-
-
-
-
3-hydroxybenzoic acid + UDP-glucose
UDP + 1-O-(3-hydroxybenzoyl)-beta-D-glucopyranose
show the reaction diagram
-
-
-
-
4-aminobenzoic acid + UDP-glucose
UDP + 4-aminobenzoyl-beta-D-glucoside
show the reaction diagram
-
-
-
-
4-chlorocinnamic acid + UDP-glucose
?
show the reaction diagram
-
56% of the activity with cinnamic acid
-
-
?
5-hydroxyferulic acid + UDP-glucose
UDP + 5-hydroxyferuloyl-beta-D-glucoside
show the reaction diagram
-
-
-
-
anthranilic acid + UDP-glucose
?
show the reaction diagram
-
11% of the activity with cinnamic acid
-
-
?
benzoic acid + UDP-glucose
UDP + benzoyl-beta-D-glucoside
show the reaction diagram
-
-
-
-
caffeic acid + UDP-glucose
UDP + caffeoyl-beta-D-glucoside
show the reaction diagram
-
-
-
-
cinnamic acid + UDP-glucose
UDP + cinnamoyl-beta-D-glucoside
show the reaction diagram
ferulic acid + UDP-glucose
UDP + feruloyl-beta-D-glucoside
show the reaction diagram
-
-
-
-
nicotinic acid + UDP-glucose
?
show the reaction diagram
-
5% of the activity with cinnamic acid
-
-
?
p-coumaric acid + UDP-glucose
UDP + p-coumaroyl-beta-D-glucoside
show the reaction diagram
-
-
-
-
p-hydroxybenzoic acid + UDP-glucose
UDP + 4-hydroxybenzoyl-beta-D-glucoside
show the reaction diagram
-
-
-
-
phenylbutyric acid + UDP-glucose
UDP + phenylbutyryl-beta-D-glucoside
show the reaction diagram
-
-
-
-
phenylpropionic acid + UDP-glucose
UDP + phenylpropionyl-beta-D-glucoside
show the reaction diagram
-
-
-
-
sinapic acid + UDP-glucose
UDP + sinapoyl-beta-D-glucoside
show the reaction diagram
-
-
-
-
sorbic acid + UDP-glucose
?
show the reaction diagram
-
126% of the activity with cinnamic acid
-
-
?
trans-2-hexenoic acid + UDP-glucose
?
show the reaction diagram
-
12% of the activity with cinnamic acid
-
-
?
trans-3-(2-furyl)acrylic acid + UDP-glucose
?
show the reaction diagram
-
94% of the activity with cinnamic acid
-
-
?
trans-3-(3-pyridyl)acrylic acid + UDP-glucose
?
show the reaction diagram
-
9% of the activity with cinnamic acid
-
-
?
UDP-alpha-D-glucose + caffeate
UDP + 1-O-caffeoyl-beta-D-glucose
show the reaction diagram
-
glucosylation at 15% the rate of cinnamate
-
-
?
UDP-alpha-D-glucose + cinnamate
UDP + 1-O-cinnamoyl-beta-D-glucose
show the reaction diagram
UDP-alpha-D-glucose + ferulate
UDP + 1-O-feruloyl-beta-D-glucose
show the reaction diagram
UDP-alpha-D-glucose + quercetin
UDP + quercetin 3-O-beta-D-glucoside
show the reaction diagram
-
-
-
-
?
UDP-glucose + 2,3-dimethoxybenzyl alcohol
UDP + 2,3-dimethoxybenzyl beta-D-glucoside
show the reaction diagram
Verbesina caracasana
-
-
-
?
UDP-glucose + 2,4-dimethoxybenzyl alcohol
UDP + 2,4-dimethoxybenzyl beta-D-glucose
show the reaction diagram
Verbesina caracasana
-
-
-
?
UDP-glucose + 2,4-dimethoxycinnamate
UDP + 2,4-dimethoxycinnamoyl beta-D-glucoside
show the reaction diagram
Verbesina caracasana
-
-
-
?
UDP-glucose + 2,5-dimethoxybenzyl alcohol
UDP + 2,5-dimethoxybenzyl beta-D-glucose
show the reaction diagram
Verbesina caracasana
-
-
-
?
UDP-glucose + 2,5-dimethoxycinnamate
UDP + 2,5-dimethoxycinnamoyl beta-D-glucose
show the reaction diagram
Verbesina caracasana
-
-
-
?
UDP-glucose + 2,6-dimethoxycinnamate
UDP + 2,6-dimethoxycinnamoyl beta-D-glucoside
show the reaction diagram
Verbesina caracasana
-
-
-
?
UDP-glucose + 2-methoxycinnamate
UDP + 2-methoxycinnamoyl beta-D-glucoside
show the reaction diagram
Verbesina caracasana
-
-
-
?
UDP-glucose + 3,4,5-trimethoxycinnamate
UDP + 3,4,5-trimethoxycinnamoyl beta-D-glucoside
show the reaction diagram
-
glucosylation at 84% the rate of 4-methoxycinnamate
-
-
?
UDP-glucose + 3,4-dimethoxybenzyl alcohol
UDP + 3,4-dimethoxybenzyl beta-D-glucose
show the reaction diagram
Verbesina caracasana
-
-
-
?
UDP-glucose + 3,4-dimethoxycinnamate
UDP + 3,4-dimethoxycinnamoyl beta-D-glucose
show the reaction diagram
UDP-glucose + 3,5-dimethoxycinnamate
UDP + 3,5-dimethoxycinnamoyl beta-D-glucoside
show the reaction diagram
Verbesina caracasana
-
-
-
?
UDP-glucose + 3-methoxycinnamate
UDP + 3-methoxycinnamoyl beta-D-glucoside
show the reaction diagram
-
glucosylation at 52% the rate of 4-methoxycinnamate
-
-
?
UDP-glucose + 4-hydroxy-3-methoxycinnamate
UDP + 4-hydroxy-3-methoxycinnamoyl beta-D-glucoside
show the reaction diagram
-
glucosylation at 35% the rate of cinnamate
-
-
?
UDP-glucose + 4-methoxycinnamate
UDP + 4-methoxycinnamoyl beta-D-glucose
show the reaction diagram
UDP-glucose + benzoate
UDP + benzoyl-beta-D-glucoside
show the reaction diagram
-
glucosylation at 71% the rate of cinnamate
-
-
?
UDP-glucose + eugenol
UDP + eugenyl beta-D-glucoside
show the reaction diagram
-
-
-
-
?
UDP-glucose + isoeugenol
UDP + isoeugenyl beta-D-glucoside
show the reaction diagram
-
-
-
-
?
UDP-glucose + isoferulic acid
UDP + isoferuloyl beta-D-glucose
show the reaction diagram
-
glucosylation at 46% the rate of 4-methoxycinnamate
-
-
?
UDP-glucose + o-coumarate
UDP + o-coumaroyl beta-D-glucose
show the reaction diagram
-
glucosylation at 52% the rate of cinnamate
-
-
?
UDP-glucose + p-coumarate
UDP + p-coumaroyl-D-glucose
show the reaction diagram
UDP-glucose + p-coumaric acid
UDP + p-coumaroyl beta-D-glucose
show the reaction diagram
-
-
-
-
?
UDP-glucose + sinapic acid
UDP + sinapoyl beta-D-glucose
show the reaction diagram
-
glucosylation at 6.5% the rate of 4-methoxycinnamate
-
-
?
vanillic acid + UDP-glucose
UDP + vannilyl-beta-D-glucoside
show the reaction diagram
-
-
-
-
additional information
?
-
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-alpha-D-glucose + cinnamate
UDP + 1-O-cinnamoyl-beta-D-glucose
show the reaction diagram
additional information
?
-
-
catalyzes the formation of cinnamic acid and p-coumaric acid glucose esters during strawberry fruit ripening, experimental results suggest that FaGT2 is involved in the detoxification of xenobiotics in accordance to its induction by oxidative stress
-
-
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Cu2+
the addition of 1 mM leads to a loss of 30% to 50%, the addition to 10 mM causes a loss of more than 90% of activity
Fe2+
the addition of 1 mM leads to a loss of 30% to 50%, the addition to 10 mM causes a loss of more than 60% of activity
Mn2+
the addition to 10 mM causes a loss of 30% of activity
Zn2+
the addition of 1 mM leads to a loss of 30% to 50%, the addition to 10 mM causes a loss of more than 90% of activity
additional information
-
no activation by MgCl2, CaCl2 or MnCl2, 1 mM each
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
HgCl2
-
strong
p-chloromercuribenzoate
-
-
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.14
2,4,5-Trichlorophenol
-
pH 8.0, 21C
0.108
3,4-dimethoxycinnamic acid
-
2.85
3,5-dichloro-4-hydroxybenzoic acid
-
pH 8.0, 21C
0.4882
3-aminobenzoic acid
-
0.4644
3-Hydroxybenzoic acid
-
0.4371
4-Aminobenzoic acid
-
0.58
4-chlorocinnamic acid
-
pH 8.0, 21C
0.3157
5-hydroxyferulic acid
-
2.74
anthranilic acid
-
pH 8.0, 21C
0.5026
Benzoic acid
-
0.7077
caffeic acid
-
0.3569 - 0.73
Cinnamic acid
0.3585
ferulic acid
-
2.75
nicotinic acid
-
pH 8.0, 21C
0.6035
p-coumaric acid
-
0.6424
p-hydroxybenzoic acid
-
0.431
phenylbutyric acid
-
0.4112
phenylpropionic acid
-
0.3002
Sinapic acid
-
3.23
sorbic acid
-
pH 8.0, 21C
5.76
trans-2-hexenoic acid
-
pH 8.0, 21C
1.33
trans-3-(2-furyl)acrylic acid
-
pH 8.0, 21C
0.93
trans-3-(3-pyridyl)acrylic acid
-
pH 8.0, 21C
0.2
trans-cinnamic acid
-
-
0.0808 - 0.1
UDP-glucose
0.5153
vanillic acid
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
Vmax is 2.34 nkat/mg for cinnamic acid, 2.69 nkat/mg for p-coumaric acid, 2.59 nkat/mg for caffeic acie, 1.65 nkat/mg for ferulic acid, 2.24 nkat/mg for 5-hydroxyferulic acid, 1.21 nkat/mg for sinapic acid, 1.08 nkat/mg for benzoic acid, 1.05 nkat/mg for 3-hydroxybenzoic acid, 0.77 nkat/mg for p-hydroxybenzoic acid, 1.69 nkat/mg for vanillic acid, 0.68 nkat/mg for 3,4-dimethoxycinnamic acid, 0.17 nkat/mg for phenylpropionic acid, 0.22 nkat/mg for phenylbutyric acid, 0.75 nkat/mg for 3-aminobenzoic acid, 1.73 nkat/mg for 4-aminobenzoic acid and 4.88 nkat/mg for UDP-glucose (with cinnamic acid). Enzyme activity is assayed in 100 mM Tris-HCL buffer, pH 8.0, containing 5 mM 2-mercaptoethanol, 10% glycerol, and 5 mM sodium disulfite. The aglycon concentration is varied from 2 microM to 2 mM, at constant (5 mM) UDP-Glc concentration at 21C.
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
maximum enzymic activity in pre-logarithmic to logarithmic growth phase
Manually annotated by BRENDA team
FaGT2 mRNA is detectable in flowers
Manually annotated by BRENDA team
at different ripening stages, the amount of FaGT2 mRNA increases strongly along the fruit-ripening stages, with maximal expression value in fully ripe red fruit.
Manually annotated by BRENDA team
FaGT2 mRNA is barely detectable in leaves
Manually annotated by BRENDA team
FaGT2 mRNA is detectable in petioles
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
45000
-
gel filtration
51600
-
X * 51600, calculated
61400
estimated molecular mass
65000
FaGT2 fusion protein, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
-
X * 51600, calculated
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
freezing inactivates, sorbitol stabilizes
-
PMSF and 2-mercaptoethanol stabilize during purification
-
sorbitol, 10%, stabilizes during storage
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, 10% sorbitol, about 10% loss of activity within 30 days
-
sorbitol, 10%, stabilizes during storage
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
partial
recombinant protein using His-tag
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli BL21 (DE3) pLysS
His-tag fusion protein expressed in Escherichia coli BL21(DE3)pLysS
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
transgenic strawberry plants expressing the FaGT2 gene in antisense orientation under the control of the cauliflower mosaic virus 35S promotor. Two of the transgenic strawberry lines contain reduced levels of cinnamoyl- and p-coumaroyl-D-glucose in comparison with the control group. The mutants do not significantly differ in the concentration of caffeoyl-, feruloyl-, and p-hydroxylbenzoyl-D-glucose, when compared with controls.