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Information on EC 2.4.1.360 - 2-hydroxyflavanone C-glucosyltransferase
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EC Tree
2.4.1.360 2-hydroxyflavanone C-glucosyltransferaseIUBMB Comments
The enzyme has been characterized in Oryza sativa (rice), various Citrus spp., Glycine max (soybean), and Fagopyrum esculentum (buckwheat). Flavanone substrates require a 2-hydroxy group. The meta-stable flavanone substrates such as 2-hydroxynaringenin exist in an equilibrium with open forms such as 1-(4-hydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propane-1,3-dione, which are the actual substrates for the glucosyl-transfer reaction (see EC 1.14.14.162, flavanone 2-hydroxylase). The enzyme can also act on dihydrochalcones. The enzymes from citrus plants can catalyse a second C-glycosylation reaction at position 5.
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Word Map
- 2.4.1.360
-
c-glucosylation
- flavonoid
-
c-glycosyltransferases
- sativa
-
o-glucosyltransferase
- dehydratase
-
o-glycosylated
-
planta
-
c-glycosylflavones
- flavone
-
cereals
- phloretin
- synthesis
- dibenzoylmethane
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
+
=
+
+
a 2'-hydroxy-beta-oxodihydrochalcone
=
+
Synonyms
oscgt, fccgt, ugt708c1, cucgt, 2-hydroxyflavanone c-glucosyltransferase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
FcCGT
OsCGT
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
UDP-alpha-D-glucose + a 2'-hydroxy-beta-oxodihydrochalcone = UDP + a 3'-(beta-D-glucopyranosyl)-2'-hydroxy-beta-oxodihydrochalcone
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
-
, , ,
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SYSTEMATIC NAME
IUBMB Comments
UDP-alpha-D-glucose:2'-hydroxy-beta-oxodihydrochalcone C6/8-beta-D-glucosyltransferase
The enzyme has been characterized in Oryza sativa (rice), various Citrus spp., Glycine max (soybean), and Fagopyrum esculentum (buckwheat). Flavanone substrates require a 2-hydroxy group. The meta-stable flavanone substrates such as 2-hydroxynaringenin exist in an equilibrium with open forms such as 1-(4-hydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propane-1,3-dione, which are the actual substrates for the glucosyl-transfer reaction (see EC 1.14.14.162, flavanone 2-hydroxylase). The enzyme can also act on dihydrochalcones. The enzymes from citrus plants can catalyse a second C-glycosylation reaction at position 5.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2 UDP-alpha-D-glucose + 2 2,5,7-trihydroxyflavanone
2 UDP + 6-(beta-D-glucopyranosyl)-2,5,7-trihydroxyflavanone + 8-(beta-D-glucopyranosyl)-2,5,7-trihydroxyflavanone
meta-stable 2-hydroxyflavanones exist in an equilibirum with their open-form dibenzoylmethane tautomers which probably are the actual glucosyl-acceptors
-
-
?
2 UDP-alpha-D-glucose + 2 2-hydroxyeriodictyol
2 UDP + 6-(beta-D-glucopyranosyl)-2-hydroxyeriodictyol + 8-(beta-D-glucopyranosyl)-2-hydroxyeriodictyol
meta-stable 2-hydroxyflavanones exist in an equilibirum with their open-form dibenzoylmethane tautomers which probably are the actual glucosyl-acceptors
-
-
?
2 UDP-alpha-D-glucose + 2 2-hydroxynaringenin
2 UDP + 6-(beta-D-glucopyranosyl)-2-hydroxynaringenin + 8-(beta-D-glucopyranosyl)-2-hydroxynaringenin
2 UDP-alpha-D-glucose + 2-hydroxyeriodictyol
2 UDP + ?
-
-
-
?
2 UDP-alpha-D-glucose + 2-hydroxynaringenin
2 UDP + 6,8-di-(beta-D-glucopyranosyl)-2-hydroxynaringenin
2 UDP-alpha-D-glucose + 2-hydroxypinocembrin
2 UDP + ?
-
-
-
?
2 UDP-alpha-D-glucose + 2-phenyl-2',4',6'-trihydroxyacetophenone
2 UDP + ?
-
-
-
?
2 UDP-alpha-D-glucose + phloretin
2 UDP + ?
-
-
-
?
UDP-alpha-D-glucose + 2',4',6'-trihydroxydihydrochalcone
UDP + ?
-
-
-
?
UDP-alpha-D-glucose + 2,4,6-trihydroxybenzophenone
UDP + ?
-
-
-
?
UDP-alpha-D-glucose + 2,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one
UDP + affinetin + H2O
the enzyme is specific for its sugar donors. It shows no activity with UDP-glucuronic acid, UDP-galactose, UDP-arabinose, or UDP-N-acetylglucosamine. Products: 40% affinetin and 27% isoaffinetin
-
-
?
UDP-alpha-D-glucose + 2,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one
UDP + isoaffinetin + H2O
the enzyme is specific for its sugar donors. It shows no activity with UDP-glucuronic acid, UDP-galactose, UDP-arabinose, or UDP-N-acetylglucosamine. Products: 40% affinetin and 27% isoaffinetin
-
-
?
UDP-alpha-D-glucose + 2,5,7-trihydroxy-2-(3-hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one
UDP + ?
the enzyme is specific for its sugar donors. It shows no activity with UDP-glucuronic acid, UDP-galactose, UDP-arabinose, or UDP-N-acetylglucosamine. Products: 14% 8-C-glucoside and 25% 6-C-glucoside
-
-
?
UDP-alpha-D-glucose + 2,5,7-trihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one
UDP + isopyrenin + H2O
the enzyme is specific for its sugar donors. It shows no activity with UDP-glucuronic acid, UDP-galactose, UDP-arabinose, or UDP-N-acetylglucosamine. Products: 69% pyrenin and 21% isopyrenin
-
-
?
UDP-alpha-D-glucose + 2,5,7-trihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one + H+
UDP + pyrenin + H2O
the enzyme is specific for its sugar donors. It shows no activity with UDP-glucuronic acid, UDP-galactose, UDP-arabinose, or UDP-N-acetylglucosamine. Products: 69% pyrenin and 21% isopyrenin
-
-
?
UDP-alpha-D-glucose + 2,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one
UDP + isoscoparin + H2O
the enzyme is specific for its sugar donors. It shows no activity with UDP-glucuronic acid, UDP-galactose, UDP-arabinose, or UDP-N-acetylglucosamine. Products: 41% scoparin and 53% isoscoparin
-
-
?
UDP-alpha-D-glucose + 2,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one
UDP + scoparin + H2O
the enzyme is specific for its sugar donors. It shows no activity with UDP-glucuronic acid, UDP-galactose, UDP-arabinose, or UDP-N-acetylglucosamine. Products: 41% scoparin and 53% isoscoparin
-
-
?
UDP-alpha-D-glucose + 2,5,7-trihydroxy-2-(4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one
UDP + cytisocide + H2O
the enzyme is specific for its sugar donors. It shows no activity with UDP-glucuronic acid, UDP-galactose, UDP-arabinose, or UDP-N-acetylglucosamine. Products: 44% cytisocide and 52% isocytisocide
-
-
?
UDP-alpha-D-glucose + 2,5,7-trihydroxy-2-(4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one
UDP + isocytisocide + H2O
the enzyme is specific for its sugar donors. It shows no activity with UDP-glucuronic acid, UDP-galactose, UDP-arabinose, or UDP-N-acetylglucosamine. Products: 44% cytisocide and 52% isocytisocide
-
-
?
UDP-alpha-D-glucose + 2,5,7-trihydroxy-2-phenyl-2,3-dihydro-4H-1-benzopyran-4-one
UDP + 6-C-glucosylchrysin + H2O
the enzyme is specific for its sugar donors. It shows no activity with UDP-glucuronic acid, UDP-galactose, UDP-arabinose, or UDP-N-acetylglucosamine. Products: 33% 8-C-glucosylchrysin and 47% 6-C-glucosylchrysin
-
-
?
UDP-alpha-D-glucose + 2,5,7-trihydroxy-2-phenyl-2,3-dihydro-4H-1-benzopyran-4-one
UDP + 8-C-glucosylchrysin + H2O
the enzyme is specific for its sugar donors. It shows no activity with UDP-glucuronic acid, UDP-galactose, UDP-arabinose, or UDP-N-acetylglucosamine. Products: 33% 8-C-glucosylchrysin and 47% 6-C-glucosylchrysin
-
-
?
UDP-alpha-D-glucose + 2,5,7-trihydroxy-2-phenyl-2,3-dihydro-4H-1-benzopyran-4-one
UDP + ?
-
-
-
-
?
UDP-alpha-D-glucose + 2,5,7-trihydroxy-2-[4-(trifluoromethyl)phenyl]-2,3-dihydro-4H-1-benzopyran-4-one
UDP + ?
the enzyme is specific for its sugar donors. It shows no activity with UDP-glucuronic acid, UDP-galactose, UDP-arabinose, or UDP-N-acetylglucosamine. Products: 34% 8-C-glucoside and 42% 6-C-glucoside
-
-
?
UDP-alpha-D-glucose + 2-(3,5-dihydroxyphenyl)-2,5,7-trihydroxy-2,3-dihydro-4H-1-benzopyran-4-one
UDP + ?
the enzyme is specific for its sugar donors. It shows no activity with UDP-glucuronic acid, UDP-galactose, UDP-arabinose, or UDP-N-acetylglucosamine. Products: 47% 8-C-glucoside and 43% 6-C-glucoside
-
-
?
UDP-alpha-D-glucose + 2-(3-fluoro-4-hydroxyphenyl)-2,5,7-trihydroxy-2,3-dihydro-4H-1-benzopyran-4-one
UDP + ?
UDP-alpha-D-glucose + 2-(4-ethoxyphenyl)-2,5,7-trihydroxy-2,3-dihydro-4H-1-benzopyran-4-one
UDP + ?
the enzyme is specific for its sugar donors. It shows no activity with UDP-glucuronic acid, UDP-galactose, UDP-arabinose, or UDP-N-acetylglucosamine. Products: 34% 8-C-glucoside and 38% 6-C-glucoside
-
-
?
UDP-alpha-D-glucose + 2-(4-fluorophenyl)-2,5,7-trihydroxy-2,3-dihydro-4H-1-benzopyran-4-one
UDP + ?
the enzyme is specific for its sugar donors. It shows no activity with UDP-glucuronic acid, UDP-galactose, UDP-arabinose, or UDP-N-acetylglucosamine. Products: 45% 8-C-glucoside and 47% 6-C-glucoside
-
-
?
UDP-alpha-D-glucose + 2-hydroxyeriodictyol
UDP + isoorientin + H2O
the enzyme is specific for its sugar donors. It shows no activity with UDP-glucuronic acid, UDP-galactose, UDP-arabinose, or UDP-N-acetylglucosamine. Products: 43% orientin and 56% isoorientin
-
-
?
UDP-alpha-D-glucose + 2-hydroxyeriodictyol
UDP + orientin + H2O
the enzyme is specific for its sugar donors. It shows no activity with UDP-glucuronic acid, UDP-galactose, UDP-arabinose, or UDP-N-acetylglucosamine. Products: 43% orientin and 56% isoorientin
-
-
?
UDP-alpha-D-glucose + 2-hydroxynaringenin
UDP + 6-(beta-D-glucopyranosyl)-2-hydroxynaringenin
-
-
-
?
UDP-alpha-D-glucose + 2-hydroxynaringenin
UDP + 8-(beta-D-glucopyranosyl)-2-hydroxynaringenin
-
-
-
?
UDP-alpha-D-glucose + 2-hydroxynaringenin
UDP + ?
-
-
-
?
UDP-alpha-D-glucose + a 2'-hydroxy-beta-oxodihydrochalcone
UDP + a 3'-(beta-D-glucopyranosyl)-2'-hydroxy-beta-oxodihydrochalcone
-
-
-
?
UDP-alpha-D-glucose + benzyl 2,4,6-trihydroxybenzoate
UDP + ?
-
-
-
?
2 UDP-alpha-D-glucose + 2 2-hydroxynaringenin
2 UDP + 6-(beta-D-glucopyranosyl)-2-hydroxynaringenin + 8-(beta-D-glucopyranosyl)-2-hydroxynaringenin
the meta-stable 2-hydroxynaringenin exists in an equilibirum with its open-form 1-(4-hydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propane-1,3-dione which is the actual glucosyl-acceptor
-
-
?
2 UDP-alpha-D-glucose + 2 2-hydroxynaringenin
2 UDP + 6-(beta-D-glucopyranosyl)-2-hydroxynaringenin + 8-(beta-D-glucopyranosyl)-2-hydroxynaringenin
the meta-stable 2-hydroxynaringenin exists in an equilibirum with its open-form 1-(4-hydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propane-1,3-dione which is the actual glucosyl-acceptor
-
-
?
2 UDP-alpha-D-glucose + 2-hydroxynaringenin
2 UDP + 6,8-di-(beta-D-glucopyranosyl)-2-hydroxynaringenin
-
-
-
-
?
2 UDP-alpha-D-glucose + 2-hydroxynaringenin
2 UDP + 6,8-di-(beta-D-glucopyranosyl)-2-hydroxynaringenin
-
-
-
-
?
2 UDP-alpha-D-glucose + 2-hydroxynaringenin
2 UDP + 6,8-di-(beta-D-glucopyranosyl)-2-hydroxynaringenin
-
-
-
?
2 UDP-alpha-D-glucose + phloretin
2 UDP + 3',5'-di-(beta-D-glucopyranosyl)phloretin
-
-
-
-
?
2 UDP-alpha-D-glucose + phloretin
2 UDP + 3',5'-di-(beta-D-glucopyranosyl)phloretin
-
-
-
-
?
UDP-alpha-D-galactose + 2-hydroxypinocembrin
UDP + ?
-
low activity with sugar donor UDP-alpha-D-galactose
-
-
?
UDP-alpha-D-galactose + 2-hydroxypinocembrin
UDP + ?
-
low activity with sugar donor UDP-alpha-D-galactose
-
-
?
UDP-alpha-D-glucose + 2-(3-fluoro-4-hydroxyphenyl)-2,5,7-trihydroxy-2,3-dihydro-4H-1-benzopyran-4-one
UDP + ?
the enzyme is specific for its sugar donors. It shows no activity with UDP-glucuronic acid, UDP-galactose, UDP-arabinose, or UDP-N-acetylglucosamine. Products: 17% 8-C-glucoside and 27% 6-C-glucoside
-
-
?
UDP-alpha-D-glucose + 2-(3-fluoro-4-hydroxyphenyl)-2,5,7-trihydroxy-2,3-dihydro-4H-1-benzopyran-4-one
UDP + ?
the enzyme is specific for its sugar donors. It shows no activity with UDP-glucuronic acid, UDP-galactose, UDP-arabinose, or UDP-N-acetylglucosamine. Products: 42% 8-C-glucoside and 56% 6-C-glucoside
-
-
?
UDP-alpha-D-glucose + 2-hydroxynaringenin
UDP + isovitexin + H2O
-
-
-
-
?
UDP-alpha-D-glucose + 2-hydroxynaringenin
UDP + isovitexin + H2O
the enzyme is specific for its sugar donors. It shows no activity with UDP-glucuronic acid, UDP-galactose, UDP-arabinose, or UDP-N-acetylglucosamine. Products: 44% vitexin and 53% isovitexin
-
-
?
UDP-alpha-D-glucose + 2-hydroxynaringenin
UDP + vitexin + H2O
the enzyme is specific for its sugar donors. It shows no activity with UDP-glucuronic acid, UDP-galactose, UDP-arabinose, or UDP-N-acetylglucosamine. Products: 44% vitexin and 53% isovitexin
-
-
?
UDP-alpha-D-glucose + 2-phenyl-2',4',6'-trihydroxyacetophenone
UDP + ?
-
-
-
-
?
UDP-alpha-D-glucose + 2-phenyl-2',4',6'-trihydroxyacetophenone
UDP + ?
-
-
-
-
?
UDP-alpha-D-xylose + 6-beta-D-glucopyranosyl-2-hydroxynaringenin
UDP + ?
-
-
-
-
?
UDP-alpha-D-xylose + 6-beta-D-glucopyranosyl-2-hydroxynaringenin
UDP + ?
-
-
-
-
?
additional information
?
-
-
no activity with naringenin, apigenin, quercetin, isoliquiritigenin, propyl gallate, and 2',4'dihydroxyacetophenone suggesting that 2',4',6'-trihydroxyacetophenone-like structures are necessary for substrates to be acceptable. Very low activity with phloridzin
-
-
?
additional information
?
-
-
no activity with naringenin, apigenin, quercetin, isoliquiritigenin, propyl gallate, and 2',4'dihydroxyacetophenone suggesting that 2',4',6'-trihydroxyacetophenone-like structures are necessary for substrates to be acceptable. Very low activity with phloridzin
-
-
?
additional information
?
-
no activity with quercetin, luteorin, apigenin
-
-
?
additional information
?
-
no activity with quercetin, luteorin, apigenin
-
-
?
additional information
?
-
-
no activity with 2,5-dihydroxyflavanone or 2,4-dihydroxydibenzoylmethane. The enzyme also transfered the sugar moiety from UDP-Gal and UDP-Xyl to the aglycon by forming a C-glycosidic linkage, but not from UDP-GlcA
-
-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
UDP-alpha-D-glucose + 2-hydroxynaringenin
UDP + ?
-
-
-
?
UDP-alpha-D-glucose + a 2'-hydroxy-beta-oxodihydrochalcone
UDP + a 3'-(beta-D-glucopyranosyl)-2'-hydroxy-beta-oxodihydrochalcone
-
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
Mg2+, Ca2+, Co2+ and Cu2+ have no significant effect in activity
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
2,4-dihydroxydibenzoylmethane
-
aglycon concentrations higher than 0.05 mM inhibit the reaction; competitive inhibitor
2-hydroxynaringenin
-
aglycon concentrations higher than 0.05 mM inhibit the reaction
additional information
-
concentrations of the glucosyldonor up to 0.5 mM increase the rate of product formation. EDTA has no significant effect in activity
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0083
2',4',6'-trihydroxydihydrochalcone
pH and temperature not specified in the publication
0.008
2,4,6-trihydroxybenzophenone
pH and temperature not specified in the publication
0.0165
2,5,7-trihydroxyflavanone
pH and temperature not specified in the publication
0.112
6-beta-D-glucopyranosyl-2-hydroxynaringenin
-
50 mM potassium phosphate buffer, pH 8.0, containing 5 mM 2-mercaptoethanol and 0.01% BSA, 30°C
0.0144
nothofagin
-
50 mM potassium phosphate buffer, pH 8.0, containing 5 mM 2-mercaptoethanol and 0.01% BSA, 30°C
0.00478
phloretin
pH and temperature not specified in the publication
0.0715
UDP-alpha-D-glucose
-
50 mM potassium phosphate buffer, pH 8.0, containing 5 mM 2-mercaptoethanol and 0.01% BSA, 30°C, nothofagin as sugar acceptor
0.00085
2-hydroxynaringenin
-
50 mM potassium phosphate buffer, pH 8.0, containing 5 mM 2-mercaptoethanol and 0.01% BSA, 30°C
0.0025
2-hydroxynaringenin
pH and temperature not specified in the publication
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.75
2',4',6'-trihydroxydihydrochalcone
pH and temperature not specified in the publication
0.11
2,4,6-trihydroxybenzophenone
pH and temperature not specified in the publication
0.76
2,5,7-trihydroxyflavanone
pH and temperature not specified in the publication
5.7
6-beta-D-glucopyranosyl-2-hydroxynaringenin
-
50 mM potassium phosphate buffer, pH 8.0, containing 5 mM 2-mercaptoethanol and 0.01% BSA, 30°C
5.3
nothofagin
-
50 mM potassium phosphate buffer, pH 8.0, containing 5 mM 2-mercaptoethanol and 0.01% BSA, 30°C
0.8
UDP-alpha-D-glucose
-
50 mM potassium phosphate buffer, pH 8.0, containing 5 mM 2-mercaptoethanol and 0.01% BSA, 30°C, nothofagin as sugar acceptor
3.13
2-hydroxynaringenin
pH and temperature not specified in the publication
7.6
2-hydroxynaringenin
-
50 mM potassium phosphate buffer, pH 8.0, containing 5 mM 2-mercaptoethanol and 0.01% BSA, 30°C
10.84
phloretin
pH and temperature not specified in the publication
12
phloretin
-
50 mM potassium phosphate buffer, pH 8.0, containing 5 mM 2-mercaptoethanol and 0.01% BSA, 30°C
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
91.2
2',4',6'-trihydroxydihydrochalcone
pH and temperature not specified in the publication
137
2,4,6-trihydroxybenzophenone
pH and temperature not specified in the publication
46.2
2,5,7-trihydroxyflavanone
pH and temperature not specified in the publication
2269
3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
pH and temperature not specified in the publication
0.51
6-beta-D-glucopyranosyl-2-hydroxynaringenin
-
50 mM potassium phosphate buffer, pH 8.0, containing 5 mM 2-mercaptoethanol and 0.01% BSA, 30°C
0.037
nothofagin
-
50 mM potassium phosphate buffer, pH 8.0, containing 5 mM 2-mercaptoethanol and 0.01% BSA, 30°C
0.11
UDP-alpha-D-glucose
-
50 mM potassium phosphate buffer, pH 8.0, containing 5 mM 2-mercaptoethanol and 0.01% BSA, 30°C, nothofagin as sugar acceptor
0.0089
2-hydroxynaringenin
-
50 mM potassium phosphate buffer, pH 8.0, containing 5 mM 2-mercaptoethanol and 0.01% BSA, 30°C
1254
2-hydroxynaringenin
pH and temperature not specified in the publication
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
8 - 11
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
metabolism
the enzyme is involved in the proposed biosynthetic pathway of C-glucosylflavones in buckwheat, overview. It starts with the hydroxylation of the 2-position of flavanone, which is the intermedixadate product of flavonol biosynthesis. The produced 2-hydroxyflavanone is in equilibrium with one of its open-circular forms (2',4',6'-trihydroxyacetophenone-like structure, dibenzoylxadmethane form), which is C-glucosylated by CGT. The formed C-glucoside is also in equilibrium with its two closed-circular forms, that is, 2-hydroxyflavanone 6-C-glucoside and 8-C-glucoside, because the sugar moiety of the open-circular form of C-glucoside can be rotated. They are then enzymatically dehydrated to produce two C-glucosylflavones
physiological function
FeCGT enxadzymes (UGT708C1 and UGT708C2) show C-glucosylation activity toward 2-hydroxyflavanones and related compounds having a 2',4',6'-trihydroxyacetophenone-like structure but not toward flavones or flavonols, indicating that the open-circular form of 2-hydroxyflavanones is their substrate
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). 708C1_FAGES
457
0
50375
Swiss-Prot
other Location (Reliability: 2)
708C2_FAGES
457
0
50433
Swiss-Prot
other Location (Reliability: 2)
708D1_SOYBN
480
0
52515
Swiss-Prot
other Location (Reliability: 5)
708G1_CITJP
472
0
51611
Swiss-Prot
other Location (Reliability: 3)
708G2_CITUN
472
0
51624
Swiss-Prot
other Location (Reliability: 3)
CGT_ORYSI
471
0
49431
Swiss-Prot
other Location (Reliability: 4)
CGT_ORYSJ
471
0
49457
Swiss-Prot
other Location (Reliability: 4)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
49430
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
purification via a nickel-affinity column, concentration using Amicon-Ultra-15 Ultracel-10k
purification via a nickel-affinity column, concentration using Amicon-Ultra-15 Ultracel-10k
purification via a nickel-affinity column, concentration using Amicon-Ultra-15 Ultracel-10k
-
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli Rosetta 2(DE3)
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
synthesis
biosynthesis of natural and novel C-glycosylflavones utilising recombinant Oryza sativa C-glycosyltransferase and Desmodium incanum root proteins
synthesis
production of C-glucosides of flavonoids and related compounds (i.e., 2-hydroxyflavanone, dihydrochalcone, and trihydroxyacetophenone) by Escherichia coli expressing C-glucosyltransferase from Fagopyrum esculentum. The substrates in their respective cultures were taken up by the cells and C-glucosylated, and the products were released into the culture media. The bioconversion process was completed in 1-2 h, but products were already observed immediately after addition of the substrates (0.2 mM). The conversion rates of these substrates reaches 80-95%
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Hirade, Y.; Kotoku, N.; Terasaka, K.; Saijo-Hamano, Y.; Fukumoto, A.; Mizukami, H.
Identification and functional analysis of 2-hydroxyflavanone C-glucosyltransferase in soybean (Glycine max)
FEBS Lett.
589.
1778-1786
2015
Glycine max (I1L3T1), Glycine max
brenda
Brazier-Hicks, M.; Evans, K.M.; Gershater, M.C.; Puschmann, H.; Steel, P.G.; Edwards, R.
The C-glycosylation of flavonoids in cereals
J. Biol. Chem.
284
17926-17934
2009
Oryza sativa Indica Group (A2YJ67), Oryza sativa Indica Group (C3W7B0)
brenda
Nagatomo, Y.; Usui, S.; Ito, T.; Kato, A.; Shimosaka, M.; Taguchi, G.
Purification, molecular cloning and functional characterization of flavonoid C-glucosyltransferases from Fagopyrum esculentum M. (buckwheat) cotyledon
Plant J.
80.
437-448
2014
Fagopyrum esculentum (A0A0A1H7N4), Fagopyrum esculentum (A0A0A1HA03)
brenda
Ito, T.; Fujimoto, S.; Suito, F.; Shimosaka, M.; Taguchi, G.
C-Glycosyltransferases catalyzing the formation of di-C-glucosyl flavonoids in citrus plants
Plant J.
91
187-198
2017
Citrus unshiu, Citrus japonica
brenda
Gutmann, A.; Nidetzky, B
.: Enzymatic C-glycosylation: Insights from the study of a complementary pair of plant O- and C-glucosyltransferases
Pure Appl. Chem.
85
1865-1877
2013
Oryza sativa Indica Group (C3W7B0)
-
brenda
Kerscher, F.; Franz, G.
Isolation and Some Properties of an UDP-glucose 2-hydroxyflavanone-6(or 8)-C-glucosyltransferase from Fagopyrum esculentum M. cotyledons
J. Plant Physiol.
132
110-115
1988
Fagopyrum esculentum
-
brenda
Hao, B.; Caulfield, J.C.; Hamilton, M.L.; Pickett, J.A.; Midega, C.A.; Khan, Z.R.; Wang, J.; Hooper, A.M.
Biosynthesis of natural and novel C-glycosylflavones utilising recombinant Oryza sativa C-glycosyltransferase (OsCGT) and Desmodium incanum root proteins
Phytochemistry
125
73-87