Information on EC 2.4.1.218 - hydroquinone glucosyltransferase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.4.1.218
-
RECOMMENDED NAME
GeneOntology No.
hydroquinone glucosyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
UDP-glucose + hydroquinone = UDP + hydroquinone-O-beta-D-glucopyranoside
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
phospho group transfer
-
-
-
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SYSTEMATIC NAME
IUBMB Comments
UDP-glucose:hydroquinone-O-beta-D-glucosyltransferase
Hydroquinone is the most effective acceptor, but over 40 phenolic compounds are also glucosylated, but at lower rates.
CAS REGISTRY NUMBER
COMMENTARY hide
37341-98-3
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
UniProt
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
CDP-glucose + hydroquinone
CDP + hydroquinone-O-beta-D-glucopyranoside
show the reaction diagram
2% of the activity with UDPglucose
-
-
?
TDP-glucose + hydroquinone
TDP + hydroquinone-O-beta-D-glucopyranoside
show the reaction diagram
68.8% of the activity with UDPglucose
-
-
?
UDP-alpha-D-glucose + 3-hydroxyflavone
UDP + 3-[(beta-D-glucopyranosyl)oxy]-flavone
show the reaction diagram
5.4% of the activity with hydroquinone
-
-
?
UDP-alpha-D-glucose + kaempferol
UDP + ?
show the reaction diagram
1.0% of the activity with hydroquinone
-
-
?
UDP-alpha-D-glucose + quercetin
UDP + ?
show the reaction diagram
2.6% of the activity with hydroquinone
-
-
?
UDP-glucose + 2-methoxy-hydroquinone
UDP + 1-O-(4-hydroxy-2-methoxyphenyl)-beta-D-glucopyranoside
show the reaction diagram
16.7% of the activity with hydroquinone
-
-
?
UDP-glucose + 3-methoxyphenol
UDP + 1-O-(3-methoxyphenyl)-beta-D-glucopyranoside
show the reaction diagram
10.9% of the activity with hydroquinone
-
-
?
UDP-glucose + 3-methoxyphenol
UDP + 3-methoxyphenyl-beta-D-glucoside
show the reaction diagram
-
11.8% of the activity with hydroquinone, wild-type enzyme
-
-
?
UDP-glucose + 4-benzyloxyphenol
UDP + (4-benzyloxyphenyl)-beta-D-glucopyranoside
show the reaction diagram
1.4% of the activity with hydroquinone
-
-
?
UDP-glucose + 4-chloro-2-methylphenol
UDP + 1-O-(4-chloro-2-methylphenyl)-beta-D-glucopyranoside
show the reaction diagram
19.0% of the activity with hydroquinone
-
-
?
UDP-glucose + 4-chlorophenol
UDP + (4-chlorophenyl)-beta-D-glucopyranoside
show the reaction diagram
7.5% of the activity with hydroquinone
-
-
?
UDP-glucose + 4-hydroxyacetophenone
UDP + (4-acetophenyl)-beta-D-glucopyranoside
show the reaction diagram
UDP-glucose + 4-hydroxybenzaldehyde
UDP + 4-beta-D-glucopyranosyloxy-benzaldehyde
show the reaction diagram
-
7.3% of the activity with hydroquinone, wild-type enzyme
-
-
?
UDP-glucose + 4-hydroxybenzaldehyde
UDP + 4-formylphenyl beta-D-glucopyranoside
show the reaction diagram
8.6% of the activity with hydroquinone
-
-
?
UDP-glucose + 4-hydroxythiophenol
UDP + (4-thiophenyl)-beta-D-glucopyranoside
show the reaction diagram
1.2% of the activity with hydroquinone
-
-
?
UDP-glucose + 4-methylphenol
UDP + (4-methylphenyl)-beta-D-glucopyranoside
show the reaction diagram
2.8% of the activity with hydroquinone
-
-
?
UDP-glucose + 4-nitrophenol
UDP + (4-nitrophenyl)-beta-D-glucopyranoside
show the reaction diagram
6.2% of the activity with hydroquinone
-
-
?
UDP-glucose + 7-hydroxyflavone
UDP + 7-beta-D-glucopyranosyloxy-2-phenylchromen-4-one
show the reaction diagram
3.0% of the activity with hydroquinone
-
-
?
UDP-glucose + 8-hydroxyquinoline
UDP + 8-hydroxyquinolin-beta-D-glucoside
show the reaction diagram
-
11.9% of the activity with hydroquinone, wild-type enzyme
-
-
?
UDP-glucose + apigenin
UDP + ?
show the reaction diagram
5.8% of the activity with hydroquinone
-
-
?
UDP-glucose + beta-naphthol
UDP + 2-naphthyl-beta-D-glucopyranoside
show the reaction diagram
-
18.4% of the activity with hydroquinone, wild-type enzyme
-
-
?
UDP-glucose + biphenol-2-ol
UDP + ?
show the reaction diagram
1.1% of the activity with hydroquinone
-
-
?
UDP-glucose + carvacrol
UDP + (2-methyl-5-isopropylphenyl)-beta-D-glucopyranoside
show the reaction diagram
1.0% of the activity with hydroquinone
-
-
?
UDP-glucose + coniferyl alcohol
UDP + coniferin
show the reaction diagram
UDP-glucose + eugenol
UDP + (4-allyl-2-methoxyphenyl)-beta-D-glucopyranoside
show the reaction diagram
UDP-glucose + eugenol
UDP + scopoletin-beta-D-glucoside
show the reaction diagram
-
4.1% of the activity with hydroquinone, wild-type enzyme
-
-
?
UDP-glucose + hydroquinone
UDP + hydroquinone-O-beta-D-glucopyranoside
show the reaction diagram
UDP-glucose + methylvanillate
UDP + 4-(beta-D-glucopyranosyloxy)-3-methoxybenzoic acid
show the reaction diagram
UDP-glucose + phenol
UDP + phenyl-beta-D-glucopyranoside
show the reaction diagram
UDP-glucose + resorcinol
UDP + (3-hydroxyphenyl)-beta-D-glucopyranoside
show the reaction diagram
UDP-glucose + resorcinol
UDP + ?
show the reaction diagram
-
7.8% of the activity with hydroquinone, wild-type enzyme
-
-
?
UDP-glucose + saligenin
UDP + 2-(hydroxymethyl)phenyl beta-D-glucopyranoside
show the reaction diagram
UDP-glucose + scopoletin
UDP + 7-beta-D-glucopyranosyloxy-6-methoxychromen-2-one
show the reaction diagram
3.0% of the activity with hydroquinone
-
-
?
UDP-glucose + scopoletin
UDP + ?
show the reaction diagram
-
3.5% of the activity with hydroquinone, wild-type enzyme
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-
?
UDP-glucose + thymol
UDP + (2-isopropyl-5-methyl-phenyl)-beta-D-glucopyranoside
show the reaction diagram
UDP-glucose + umbelliferone
UDP + 7-beta-D-glucopyranosyloxy-chromen-2-one
show the reaction diagram
3.6% of the activity with hydroquinone
-
-
?
UDP-glucose + umbelliferone
UDP + eugenol-beta-D-glucoside
show the reaction diagram
-
5.1% of the activity with hydroquinone, wild-type enzyme
-
-
?
UDP-glucose + vanillic acid
UDP + 4-(beta-D-glucopyranosyloxy)-3-methoxybenzoic acid
show the reaction diagram
UDP-glucose + vanillin
UDP + 4-beta-D-glucopyranosyloxy-3-methoxy-benzaldehyde
show the reaction diagram
UDP-glucose + vanillin
UDP + vanillin-O-beta-D-glucopyranoside
show the reaction diagram
-
10.6% of the activity with hydroquinone, wild-type enzyme
-
-
?
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-glucose + hydroquinone
UDP + hydroquinone-O-beta-D-glucopyranoside
show the reaction diagram
additional information
?
-
-
because hydroquinone and arbutin seem not to be naturally occuring compounds in Rauvolfia plants or cell culture, the enzyme must have another substrate specificity
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-
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mg2+
-
10 mM, increases the conversion rate to 168.3%
Ni2+
required, metalloenzyme
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Ca2+
-
10 mM, 24.4% inhibition
Co2+
-
10 mM, 54.2% inhibition
Hg2+
-
10 mM, complete inhibition, reversed by addition of 20 mM 2-mercaptoethanol
hydroquinone
Glu274 is acting as an acidic backbone acceptor residue. Lys262, a basic amino acid from the active site of wheat Hydroquinone glucosyltransferase interacts with the hydroxyl group of hydroquinone and behaves as a side chain donor molecule. Asp264 is also observed as an interacting residue from the active site of hydroquinone glucosyltransferase. It binds to the hydroxyl group of hydroquinone inhibitor and donates hydrogen ion from its side chain group
Mn2+
-
10 mM, 24.7% inhibition
N-(n-butyl) phosphorothiocic triamide
Glu274 is acting as an acidic backbone donor residue and interacts with the amino group of the inhibitor
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phenyl phosphorodiamate
Glu395 is directly interacting with amino group of the inhibitor
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Zn2+
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10 mM, 87.4% inhibition
additional information
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.1
TDPglucose
-
-
0.077
UDPglucose
-
-
0.55
umbelliferone
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-
0.398 - 0.706
Vanillin
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.08 - 2.59
Vanillin
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00009
dichlorophen
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-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.003
-
purified recombinant mutant H360E, substrate hydroquinone
0.01
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purified recombinant mutant H360K, substrate hydroquinone
0.013
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purified recombinant mutant H360R, substrate hydroquinone
0.054
-
purified recombinant mutant E368D, substrate vanillin
0.066
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purified recombinant mutant E368A, substrate vanillin
0.79
-
purified recombinant mutant A204V, substrate vanillin
1.07
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purified recombinant mutant E368D, substrate hydroquinone
1.22
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purified recombinant mutant L86I, substrate vanillin
1.44
-
purified recombinant mutant E368A, substrate hydroquinone
1.45
-
purified recombinant wild-type enzyme, substrate vanillin
8.34
-
purified recombinant mutant A204V, substrate hydroquinone
10.82
-
purified recombinant mutant L86I, substrate hydroquinone
12.17
-
purified recombinant wild-type enzyme, substrate hydroquinone
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4.5
-
and a second optimum at pH 6.8 in phosphate buffer, and a second optimum at pH 7.5 in citric acid buffer
6.8
-
and a second optimum at pH 4.5, phosphate buffer
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
50
-
1 h, stable
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
recombinant His-tagged wild-type and mutant enzymes from Escherichia coli by nickel affinity chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
cDNA with 6xHis tag; expression in Escherichia coli
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DNA and amino acid sequence determination and analysis, expression of His-tagged wild-type and mutant enzymes in Escherichia coli strain M15
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expression in Escherichia coli
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
A204V
-
site-directed mutagenesis, mutant shows slightly reduced activity compared to the wild-type enzyme
E368A
-
site-directed mutagenesis, mutant shows reduced activity compared to the wild-type enzyme
E368D
-
site-directed mutagenesis, mutant shows reduced activity compared to the wild-type enzyme
H360E
-
site-directed mutagenesis, mutant shows about 4000fold reduced activity compared to the wild-type enzyme
H360K
-
site-directed mutagenesis, mutant shows about 1000fold reduced activity compared to the wild-type enzyme
H360R
-
site-directed mutagenesis, mutant shows about 1000fold reduced activity compared to the wild-type enzyme
L86I
-
site-directed mutagenesis, mutant shows slightly reduced activity compared to the wild-type enzyme
additional information
-
generation of the typical E-E motif of the enzyme does not convert a NRD1beta enzyme into a NRD1alpha enzyme
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
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formation of arbutin, which is a potent inhibitor of human melanin biosynthesis with commercial value