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Information on EC 2.4.1.218 - hydroquinone glucosyltransferase and Organism(s) Rauvolfia serpentina and UniProt Accession Q9AR73
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2.4.1.218 hydroquinone glucosyltransferaseIUBMB Comments
Hydroquinone is the most effective acceptor, but over 40 phenolic compounds are also glucosylated, but at lower rates.
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The taxonomic range for the selected organisms is: Rauvolfia serpentina
The enzyme appears in selected viruses and cellular organisms
The enzyme appears in selected viruses and cellular organisms
Synonyms
hydroquinone glucosyltransferase, arbutin synthase, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
arbutin synthase
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arbutin synthetase
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glucosyltransferase, uridine diphosphoglucose-hydroquinone
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hydroquinone O-glucosyltransferase
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hydroquinone:O-glucosyltransferase
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uridine diphosphate-glucose:hydroquinone glucosyltransferase
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additional information
the enzyme belongs to the NRD1beta family of glycosyltransferases
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
UDP-glucose + hydroquinone = UDP + hydroquinone-O-beta-D-glucopyranoside
reaction mechanism, the NRD domain with residue Glu368 is required for activity, His360 is crucial for activity
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
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
37341-98-3
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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
CDP-glucose + hydroquinone
CDP + hydroquinone-O-beta-D-glucopyranoside
2% of the activity with UDPglucose
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-
?
TDP-glucose + hydroquinone
TDP + hydroquinone-O-beta-D-glucopyranoside
68.8% of the activity with UDPglucose
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?
UDP-alpha-D-glucose + 3-hydroxyflavone
UDP + 3-[(beta-D-glucopyranosyl)oxy]-flavone
5.4% of the activity with hydroquinone
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-
?
UDP-alpha-D-glucose + biphenyl-2-ol
UDP + [1,1'-biphenyl]-2-yl beta-D-glucopyranoside
1.1% of the activity with hydroquinone
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-
?
UDP-alpha-D-glucose + hydroquinone
UDP + hydroquinone-O-beta-D-glucopyranoside
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-
-
?
UDP-alpha-D-glucose + kaempferol
UDP + ?
1.0% of the activity with hydroquinone
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-
?
UDP-alpha-D-glucose + quercetin
UDP + ?
2.6% of the activity with hydroquinone
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-
?
UDP-glucose + 2-methoxy-hydroquinone
UDP + 1-O-(4-hydroxy-2-methoxyphenyl)-beta-D-glucopyranoside
16.7% of the activity with hydroquinone
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-
?
UDP-glucose + 3-methoxyphenol
UDP + 1-O-(3-methoxyphenyl)-beta-D-glucopyranoside
10.9% of the activity with hydroquinone
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?
UDP-glucose + 3-methoxyphenol
UDP + 3-methoxyphenyl-beta-D-glucoside
11.8% of the activity with hydroquinone, wild-type enzyme
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?
UDP-glucose + 4-benzyloxyphenol
UDP + (4-benzyloxyphenyl)-beta-D-glucopyranoside
1.4% of the activity with hydroquinone
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-
?
UDP-glucose + 4-chloro-2-methylphenol
UDP + 1-O-(4-chloro-2-methylphenyl)-beta-D-glucopyranoside
19.0% of the activity with hydroquinone
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-
?
UDP-glucose + 4-chlorophenol
UDP + (4-chlorophenyl)-beta-D-glucopyranoside
7.5% of the activity with hydroquinone
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?
UDP-glucose + 4-hydroxyacetophenone
UDP + (4-acetophenyl)-beta-D-glucopyranoside
,1.8% of the activity with hydroquinone
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?
UDP-glucose + 4-hydroxybenzaldehyde
UDP + 4-beta-D-glucopyranosyloxy-benzaldehyde
7.3% of the activity with hydroquinone, wild-type enzyme
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?
UDP-glucose + 4-hydroxybenzaldehyde
UDP + 4-formylphenyl beta-D-glucopyranoside
8.6% of the activity with hydroquinone
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?
UDP-glucose + 4-hydroxythiophenol
UDP + (4-thiophenyl)-beta-D-glucopyranoside
1.2% of the activity with hydroquinone
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?
UDP-glucose + 4-methylphenol
UDP + (4-methylphenyl)-beta-D-glucopyranoside
2.8% of the activity with hydroquinone
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?
UDP-glucose + 4-nitrophenol
UDP + (4-nitrophenyl)-beta-D-glucopyranoside
6.2% of the activity with hydroquinone
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?
UDP-glucose + 7-hydroxyflavone
UDP + 7-beta-D-glucopyranosyloxy-2-phenylchromen-4-one
3.0% of the activity with hydroquinone
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?
UDP-glucose + 8-hydroxyquinoline
UDP + 8-hydroxyquinolin-beta-D-glucoside
11.9% of the activity with hydroquinone, wild-type enzyme
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?
UDP-glucose + apigenin
UDP + ?
5.8% of the activity with hydroquinone
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?
UDP-glucose + beta-naphthol
UDP + 2-naphthyl-beta-D-glucopyranoside
18.4% of the activity with hydroquinone, wild-type enzyme
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?
UDP-glucose + carvacrol
UDP + (2-methyl-5-isopropylphenyl)-beta-D-glucopyranoside
1.0% of the activity with hydroquinone
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?
UDP-glucose + coniferyl alcohol
UDP + coniferin
1.2% of the activity with hydroquinone
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?
UDP-glucose + methylvanillate
UDP + 4-(beta-D-glucopyranosyloxy)-3-methoxybenzoic acid
2.2% of the activity with hydroquinone
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?
UDP-glucose + phenol
UDP + phenyl-beta-D-glucopyranoside
5.1% of the activity with hydroquinone
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?
UDP-glucose + saligenin
UDP + 2-(hydroxymethyl)phenyl beta-D-glucopyranoside
9.4% of the activity with hydroquinone
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?
UDP-glucose + scopoletin
UDP + 7-beta-D-glucopyranosyloxy-6-methoxychromen-2-one
3.0% of the activity with hydroquinone
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?
UDP-glucose + scopoletin
UDP + scopoletin-beta-D-glucoside
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
7.6% of the activity with hydroquinone
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?
UDP-glucose + umbelliferone
UDP + 7-beta-D-glucopyranosyloxy-chromen-2-one
3.6% of the activity with hydroquinone
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?
UDP-glucose + umbelliferone
UDP + umbelliferyl beta-D-glucoside
5.1% of the activity with hydroquinone, wild-type enzyme
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?
UDP-glucose + vanillic acid
UDP + 4-(beta-D-glucopyranosyloxy)-3-methoxybenzoic acid
1.0% of the activity with hydroquinone
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?
UDP-glucose + vanillin
UDP + 4-beta-D-glucopyranosyloxy-3-methoxy-benzaldehyde
9.4% of the activity with hydroquinone
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?
UDP-glucose + vanillin
UDP + vanillin-O-beta-D-glucopyranoside
10.6% of the activity with hydroquinone, wild-type enzyme
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?
UDP-glucose + 4-hydroxyacetophenone
UDP + (4-acetophenyl)-beta-D-glucopyranoside
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,1.8% of the activity with hydroquinone
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?
UDP-glucose + coniferyl alcohol
UDP + coniferin
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1.2% of the activity with hydroquinone
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?
UDP-glucose + eugenol
UDP + (4-allyl-2-methoxyphenyl)-beta-D-glucopyranoside
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6.2% of the activity with hydroquinone
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?
UDP-glucose + methylvanillate
UDP + 4-(beta-D-glucopyranosyloxy)-3-methoxybenzoic acid
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2.2% of the activity with hydroquinone
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?
UDP-glucose + phenol
UDP + phenyl-beta-D-glucopyranoside
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5.1% of the activity with hydroquinone
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?
UDP-glucose + resorcinol
UDP + (3-hydroxyphenyl)-beta-D-glucopyranoside
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8.7% of the activity with hydroquinone
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?
UDP-glucose + saligenin
UDP + 2-(hydroxymethyl)phenyl beta-D-glucopyranoside
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9.4% of the activity with hydroquinone
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?
UDP-glucose + thymol
UDP + (2-isopropyl-5-methyl-phenyl)-beta-D-glucopyranoside
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7.6% of the activity with hydroquinone
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?
UDP-glucose + vanillic acid
UDP + 4-(beta-D-glucopyranosyloxy)-3-methoxybenzoic acid
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1.0% of the activity with hydroquinone
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?
UDP-glucose + vanillin
UDP + 4-beta-D-glucopyranosyloxy-3-methoxy-benzaldehyde
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9.4% of the activity with hydroquinone
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?
UDP-glucose + eugenol
UDP + (4-allyl-2-methoxyphenyl)-beta-D-glucopyranoside
6.2% of the activity with hydroquinone
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?
UDP-glucose + eugenol
UDP + (4-allyl-2-methoxyphenyl)-beta-D-glucopyranoside
4.1% of the activity with hydroquinone, wild-type enzyme
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?
UDP-glucose + hydroquinone
UDP + hydroquinone-O-beta-D-glucopyranoside
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?
UDP-glucose + hydroquinone
UDP + hydroquinone-O-beta-D-glucopyranoside
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?
UDP-glucose + hydroquinone
UDP + hydroquinone-O-beta-D-glucopyranoside
highly preferred substrate
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?
UDP-glucose + resorcinol
UDP + (3-hydroxyphenyl)-beta-D-glucopyranoside
8.7% of the activity with hydroquinone
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?
UDP-glucose + resorcinol
UDP + (3-hydroxyphenyl)-beta-D-glucopyranoside
7.8% of the activity with hydroquinone, wild-type enzyme
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?
UDP-glucose + hydroquinone
UDP + hydroquinone-O-beta-D-glucopyranoside
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?
UDP-glucose + hydroquinone
UDP + hydroquinone-O-beta-D-glucopyranoside
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?
additional information
?
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no activity with UDPmannose, UDPgalactose or UDPglucuronic acid
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?
additional information
?
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no activity with UDPmannose, UDPgalactose or UDPglucuronic acid
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?
additional information
?
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substrate specificity of wild-type and E368A mutant enzymes, overview
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?
additional information
?
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substrate specificity of wild-type and E368A mutant enzymes, overview
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?
additional information
?
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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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?
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-glucose + hydroquinone
UDP + hydroquinone-O-beta-D-glucopyranoside
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?
additional information
?
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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
LITERATURE
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Hg2+
10 mM, complete inhibition, reversed by addition of 20 mM 2-mercaptoethanol
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
additional information
Km value for hydroquinone is below 0.001 mM
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additional information
additional information
-
Km value for hydroquinone is below 0.001 mM
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additional information
additional information
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Km value for hydroquinone is below 0.001 mM
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
12.17
purified recombinant wild-type enzyme, substrate hydroquinone
additional information
additional information
substrate specificity of wild-type and E368A mutant enzymes, overview
additional information
-
substrate specificity of wild-type and E368A mutant enzymes, overview
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
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
7.5
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
50
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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). HQGT_RAUSE
470
0
51794
Swiss-Prot
other Location (Reliability: 2)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
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
additional information
generation of the typical E-E motif of the enzyme does not convert a NRD1beta enzyme into a NRD1alpha enzyme
additional information
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generation of the typical E-E motif of the enzyme does not convert a NRD1beta enzyme into a NRD1alpha enzyme
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant His-tagged wild-type and mutant enzymes from Escherichia coli by nickel affinity chromatography
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, expression of His-tagged wild-type and mutant enzymes in Escherichia coli strain M15
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
synthesis
an artificial pathway is established in Escherichia coli for high-level production of arbutin from simple carbon sources in Escherichia coli for high-level production of arbutin from simple carbon sources. Introduction of the genes for 4-hydroxybenzoate 1-hydroxylase from Candida parapsilosis CBS604 and hydroquinone glucosyltransferase from Rauvolfia serpentina into Escherichia coli leads to the production of 54.71 mg/l of arbutin from glucose. Further redirection of carbon flux into arbutin biosynthesis pathway by enhancing shikimate pathway genes enables production of 3.29 g/l arbutin. Final optimization of glucose concentration added in the culture medium is able to further improve the titer of arbutin to 4.19 g/l in shake flasks experiments
synthesis
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formation of arbutin, which is a potent inhibitor of human melanin biosynthesis with commercial value
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Arend, J.; Warzecha, H.; Stckigt, J.
Hydroquinone:O-glucosyltransferase from cultivated Rauvolfia cells: enrichment and partial amino acid sequences
Phytochemistry
53
187-193
2000
Rauvolfia serpentina
Hefner, T.; Arend, J.; Warzecha, H.; Siems, K.; Stckigt, J.
Arbutin synthase, a novel member of the NRD1beta glycosyltransferase family, is a unique multifunctional enzyme converting various natural products and xenobiotics
Bioorg. Med. Chem.
10
1731-1741
2002
Rauvolfia serpentina (Q9AR73), Rauvolfia serpentina
Arend, J.; Warzecha, H.; Hefner, T.; Stckigt, J.
Utilizing genetically engineered bacteria to produce plant-specific glucosides
Biotechnol. Bioeng.
76
126-131
2001
Rauvolfia serpentina
Hefner, T.; Stockigt, J.
Probing suggested catalytic domains of glycosyltransferases by site-directed mutagenesis
Eur. J. Biochem.
270
533-538
2003
Rauvolfia serpentina (Q9AR73), Rauvolfia serpentina
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