Information on EC 3.2.1.31 - beta-glucuronidase and Organism(s) Homo sapiens

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Homo sapiens


The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea


The taxonomic range for the selected organisms is: Homo sapiens

EC NUMBER
COMMENTARY hide
3.2.1.31
-
RECOMMENDED NAME
GeneOntology No.
beta-glucuronidase
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
beta-D-glucuronide and D-glucuronate degradation
-
-
luteolin triglucuronide degradation
-
-
degradation of sugar acids
-
-
Pentose and glucuronate interconversions
-
-
Glycosaminoglycan degradation
-
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Porphyrin and chlorophyll metabolism
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Flavone and flavonol biosynthesis
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Drug metabolism - other enzymes
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Metabolic pathways
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
beta-D-glucuronoside glucuronosohydrolase
-
CAS REGISTRY NUMBER
COMMENTARY hide
9001-45-0
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
-
beta-glucuronidase, an acid hydrolase that deconjugates glucuronides, may increase cancer risk
physiological function
-
beta-glucuronidase, an acid hydrolase that deconjugates glucuronides, may increase cancer risk
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(1S)-1-(chloromethyl)-3-([5-[2-(dimethylamino)ethoxy]-1H-indol-2-yl]carbonyl)-2,3-dihydro-1H-benzo[e]indol-5-yl beta-D-glucopyranosiduronic acid + H2O
D-glucuronate + [(1S)-1-(chloromethyl)-5-hydroxy-1,2-dihydro-3H-benzo[e]indol-3-yl][5-[2-(dimethylamino)ethoxy]-1H-indol-2-yl]methanone
show the reaction diagram
-
-
-
-
?
(1S,3S)-3,12-dihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 2,3,6-trideoxy-3-{[({2-[({[4-(beta-D-glucopyranuronosyloxy)-3-nitrobenzyl]oxy}carbonyl)amino]-5-({[(2-{[4-({[(pyridin-3-ylmethoxy)carbonyl]amino}methyl)benzoyl]amino}phenyl)carbamoyl]oxy}methyl)benzyl}oxy)carbonyl]amino}-alpha-D-lyxo-hexopyranoside + H2O
D-glucuronate + (1S,3S)-3,12-dihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 2,3,6-trideoxy-3-[({[2-({[(4-hydroxy-3-nitrobenzyl)oxy]carbonyl}amino)-5-({[(2-{[4-({[(pyridin-3-ylmethoxy)carbonyl]amino}methyl)benzoyl]amino}phenyl)carbamoyl]oxy}methyl)benzyl]oxy}carbonyl)amino]-alpha-D-lyxo-hexopyranoside
show the reaction diagram
-
-
-
-
?
1-O-([4-[(10R,11S)-10-([[(2alpha,5beta,7beta,13alpha)-4,10-bis(acetyloxy)-2-(benzoyloxy)-7-hydroxy-9-oxo-5,20-epoxytax-11-en-13-yl]oxy]carbonyl)-4-methyl-3,8,13-trioxo-11,13-diphenyl-2,7,9-trioxa-4,12-diazatridec-1-yl]phenyl]carbamoyl)-beta-D-glucuronate + H2O
D-glucuronate + [4-[(10R,11S)-10-[[((2alpha,5beta,7beta,13alpha)-4,10-bis(acetyloxy)-2-(benzoyloxy)-7-hydroxy-9-oxo-5,20-epoxytax-11-en-13-yl]oxy]carbonyl)-4-methyl-3,8,13-trioxo-11,13-diphenyl-2,7,9-trioxa-4,12-diazatridec-1-yl]phenyl]carbamic acid
show the reaction diagram
-
-
-
-
?
1-O-[(2-[[4-(acetylamino)benzoyl]amino]phenyl)carbamoyl]-beta-D-glucopyranuronic acid + H2O
D-glucuronate + (2-[[4-(acetylamino)benzoyl]amino]phenyl)carbamic acid
show the reaction diagram
-
-
-
-
?
1-O-[(4-[[([[(1S,2R)-1-(benzoylamino)-3-[[(2alpha,5beta,7beta,13alpha)-4,10-bis(acetyloxy)-2-(benzoyloxy)-7-hydroxy-9-oxo-5,20-epoxytax-11-en-13-yl]oxy]-3-oxo-1-phenylpropan-2-yl]oxy]carbonyl)oxy]methyl]phenyl)carbamoyl]-beta-D-glucopyranuronic acid + H2O
D-glucuronate + (4-[[([[(1S,2R)-1-(benzoylamino)-3-[[(2alpha,5beta,7beta,13alpha)-4,10-bis(acetyloxy)-2-(benzoyloxy)-7-hydroxy-9-oxo-5,20-epoxytax-11-en-13-yl]oxy]-3-oxo-1-phenylpropan-2-yl]oxy]carbonyl)oxy]methyl]phenyl)carbamic acid
show the reaction diagram
-
-
-
-
?
2-amino-4-[(10R,11S)-10-([[(2alpha,5beta,7beta,13alpha)-4,10-bis(acetyloxy)-2-(benzoyloxy)-7-hydroxy-9-oxo-5,20-epoxytax-11-en-13-yl]oxy]carbonyl)-4,7-dimethyl-3,8,13-trioxo-11,13-diphenyl-2,9-dioxa-4,7,12-triazatridec-1-yl]phenyl beta-D-glucopyranosiduronate + H2O
D-glucuronate + (2alpha,5beta,7beta,13alpha)-4,10-bis(acetyloxy)-2-(benzoyloxy)-7-hydroxy-9-oxo-5,20-epoxytax-11-en-13-yl (10R)-1-(3-amino-4-hydroxyphenyl)-10-[(S)-(benzoylamino)(phenyl)methyl]-4,7-dimethyl-3,8-dioxo-2,9-dioxa-4,7-diazaundecan-11-oate
show the reaction diagram
-
-
-
-
?
2-amino-4-[(10R,11S)-10-([[(2alpha,5beta,7beta,13alpha)-4,10-bis(acetyloxy)-2-(benzoyloxy)-7-hydroxy-9-oxo-5,20-epoxytax-11-en-13-yl]oxy]carbonyl)-4-methyl-3,8,13-trioxo-11,13-diphenyl-2,7,9-trioxa-4,12-diazatridec-1-yl]phenyl beta-D-glucopyranosiduronic acid + H2O
D-glucuronate + (2alpha,5beta,7beta,13alpha)-4,10-bis(acetyloxy)-2-(benzoyloxy)-7-hydroxy-9-oxo-5,20-epoxytax-11-en-13-yl (10R)-1-(3-amino-4-hydroxyphenyl)-10-[(S)-(benzoylamino)(phenyl)methyl]-4-methyl-3,8-dioxo-2,7,9-trioxa-4-azaundecan-11-oate
show the reaction diagram
-
-
-
-
?
4-([[(2-[[4-(acetylamino)benzoyl]amino]phenyl)carbamoyl]oxy]methyl)-2-nitrophenyl beta-D-glucopyranosiduronic acid + H2O
D-glucuronate + 4-hydroxy-3-nitrobenzyl (2-[[4-(acetylamino)benzoyl]amino]phenyl)carbamate
show the reaction diagram
-
-
-
-
?
4-([[(4S)-4-ethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl]oxy]methyl)-2-nitrophenyl beta-D-glucopyranosiduronic acid + H2O
D-glucuronate + (4S)-4-ethyl-4-hydroxy-9-[(4-hydroxy-3-nitrobenzyl)oxy]-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
show the reaction diagram
-
-
-
-
?
4-methylumbelliferyl beta-D-glucuronide
4-methylumbelliferone + D-glucuronic acid
show the reaction diagram
-
-
-
-
?
4-methylumbelliferyl-beta-D-glucuronide + H2O
4-methylumbelliferol + D-glucuronate
show the reaction diagram
-
-
-
-
?
4-methylumbelliferyl-beta-D-glucuronide + H2O
4-methylumbelliferone + D-glucuronic acid
show the reaction diagram
4-nitrophenyl beta-D-glucuronide + H2O
4-nitrophenol + beta-D-glucuronate
show the reaction diagram
-
-
-
-
?
4-nitrophenyl beta-D-glucuronide + H2O
4-nitrophenol + D-glucuronic acid
show the reaction diagram
4-[(10R,11S)-10-([[(2alpha,5beta,7beta,13alpha)-4,10-bis(acetyloxy)-2-(benzoyloxy)-7-hydroxy-9-oxo-5,20-epoxytax-11-en-13-yl]oxy]carbonyl)-4-methyl-3,8,13-trioxo-11,13-diphenyl-2,7,9-trioxa-4,12-diazatridec-1-yl]-2-nitrophenyl beta-D-glucuronate + H2O
D-glucuronate + (2alpha,5beta,7beta,13alpha)-4,10-bis(acetyloxy)-2-(benzoyloxy)-7-hydroxy-9-oxo-5,20-epoxytax-11-en-13-yl (10R)-10-[(S)-(benzoylamino)(phenyl)methyl]-1-(4-hydroxy-3-nitrophenyl)-4-methyl-3,8-dioxo-2,7,9-trioxa-4-azaundecan-11-oate
show the reaction diagram
-
-
-
-
?
4-[([[(3b,22S,23R)-3-hydroxy-17,23-epoxyveratraman-28-yl]carbonyl]oxy)methyl]-2-nitrophenyl beta-D-glucopyranosiduronic acid + H2O
D-glucuronate + 4-hydroxy-3-nitrobenzyl (3b,22S,23R)-3-hydroxy-17,23-epoxyveratraman-28-carboxylate
show the reaction diagram
-
-
-
-
?
4-[([[(4S)-4-ethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-10-yl]carbamoyl]oxy)methyl]phenyl beta-D-glucopyranosiduronic acid + H2O
D-glucuronate + 4-hydroxybenzyl [(4S)-4-ethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-10-yl]carbamate
show the reaction diagram
-
-
-
-
?
4-[2-[1-(2-[2-[2-(beta-D-glucopyranuronosyloxy)ethoxy]ethoxy]ethyl)-1H-1,2,3-triazol-4-yl]-1-([[(3b,22S,23R)-3-hydroxy-17,23-epoxyveratraman-28-yl]carbonyl]oxy)ethyl]-2-nitrophenyl beta-D-glucopyranosiduronic acid + H2O
D-glucuronate + 2-[2-(2-[4-[2-([[(3beta,22S,23R)-3-hydroxy-17,23-epoxyveratraman-28-yl]carbonyl]oxy)-2-(4-hydroxy-3-nitrophenyl)ethyl]-1H-1,2,3-triazol-1-yl]ethoxy)ethoxy]ethyl beta-D-glucopyranosiduronic acid
show the reaction diagram
-
-
-
-
?
daidzein 7-O-beta-D-glucuronide + H2O
daidzein + D-glucuronate
show the reaction diagram
-
-
-
-
?
equol 7-O-beta-D-glucuronide + H2O
equol + D-glucuronate
show the reaction diagram
-
-
-
-
?
kaempferol 3-O-beta-D-glucuronide + H2O
kaempferol + D-glucuronate
show the reaction diagram
-
-
-
-
?
N-([[4-(beta-D-glucopyranuronosyloxy)-3-nitrobenzyl]oxy]carbonyl)-N-methyl-L-valyl-N-[(3R,4S,5S)-1-[(2S)-2-[(1R,2R)-3-[[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]amino]-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl]-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N-met + H2O
D-glucuronate + N-[[(4-hydroxy-3-nitrobenzyl)oxy]carbonyl]-N-methyl-L-valyl-N-[(3R,4S,5S)-1-[(2S)-2-[(1R,2R)-3-[[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]amino]-1-methoxy-2-methyl-3-oxopropyl]pyrrolidin-1-yl]-3-methoxy-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide
show the reaction diagram
-
-
-
-
?
phenolphthalein-beta-D-glucuronide + H2O
phenolphthalein + D-glucuronic acid
show the reaction diagram
-
-
-
-
-
quercetin 3-O-beta-D-glucuronide + H2O
quercetin + D-glucuronate
show the reaction diagram
-
-
-
-
?
quercetin 7-O-beta-D-glucuronide + H2O
quercetin + D-glucuronate
show the reaction diagram
-
-
-
-
?
quercetin-4'-O-glucuronide + H2O
quercetin + D-glucuronate
show the reaction diagram
-
-
-
-
?
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,1'-(3-methyl-4-phenylthieno[2,3-b]thiophene-2,5-diyl)bis(4,4,4-triethoxybut-2-en-1-one)
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-
ascorbic acid
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-
azide
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50 mM, 70% loss of activity of wild-type enzyme and mutant enzyme E451A. 50 mM-0.5 M, stimulation of mutant enzyme E451A. 1 mM, inhibition of wild-type enzyme and mutant enzyme E451A
Cu2+
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D-saccharic acid 1,4-lactone
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estradiol 3-glucuronide
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fucoxanthin
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mixed-type inhibition
glycyrrhizin
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-
Hg2+
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reversed by EDTA
Inhibitor
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heat stable, competetive, in plasma
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Ni2+
-
-
paracetamol glucuronide
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saccharo-1,4-lactone
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complete inhibition of liver enzyme
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
azide
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50 mM-0.5 M, stimulation of mutant enzyme E451A
bovine serum albumin
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activation
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chlorpyrifos-methyl
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diazinon
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dichlorvos
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fenitrothion
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fenthion
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Plasma serum
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acivation
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propetamphos
-
-
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.041 - 2.76
4-methylumbelliferyl-beta-D-glucuronide
1.4
4-nitrophenyl-beta-D-glucuronide
-
pH 7.2, 37C
0.272
daidzein 7-O-beta-D-glucuronide
-
pH 7.2, 37C
0.266
equol 7-O-beta-D-glucuronide
-
pH 7.2, 37C
0.025
kaempferol 3-O-beta-D-glucuronide
-
pH 7.2, 37C
0.13 - 2.9
p-nitrophenyl-beta-D-glucuronide
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-
0.018 - 3.08
phenolphthalein glucuronide
-
dependency on pH
0.048
quercetin 4'-O-beta-D-glucuronide
-
pH 7.2, 37C
0.237
quercetin 7-O-beta-D-glucuronide
-
pH 7.2, 37C
0.167
quercetin-3-O-beta-D-glucuronide
-
pH 7.2, 37C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.004 - 276
4-methylumbelliferyl-beta-D-glucuronide
0.67
4-nitrophenyl-beta-D-glucuronide
-
pH 7.2, 37C
1.07
daidzein 7-O-beta-D-glucuronide
-
pH 7.2, 37C
0.35
equol 7-O-beta-D-glucuronide
-
pH 7.2, 37C
0.65
kaempferol 3-O-beta-D-glucuronide
-
pH 7.2, 37C
0.26
quercetin 4'-O-beta-D-glucuronide
-
pH 7.2, 37C
1.65
quercetin 7-O-beta-D-glucuronide
-
pH 7.2, 37C
1.9
quercetin-3-O-beta-D-glucuronide
-
pH 7.2, 37C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.9 - 1.2
estradiol 3-glucuronide
0.47 - 0.57
glycyrrhizin
1.6 - 2
paracetamol glucuronide
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0009
1,1'-(3-methyl-4-phenylthieno[2,3-b]thiophene-2,5-diyl)bis(4,4,4-triethoxybut-2-en-1-one)
Homo sapiens;
-
pH not specified in the publication, 37C
0.0458
D-saccharic acid 1,4-lactone
Homo sapiens;
-
pH not specified in the publication, 37C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
31.33
-
-
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
3
-
substrate 4-methylumbelliferyl-beta-D-glucuronide
4 - 4.5
-
-
4 - 5
-
mutant enzyme E451A
4.5
-
wild-type enzyme
4.6
-
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
high varability in the expression
Manually annotated by BRENDA team
-
chronic myelogenous
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
recombinant enzyme in BHK cells
Manually annotated by BRENDA team
PDB
SCOP
CATH
UNIPROT
ORGANISM
Homo sapiens;
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
75000
-
4 * 75000, SDS-PAGE
79000
-
2 * 79000, intracellular human beta-glucuronidase in transfected BHK cells, SDS-PAGE
83000
-
4 * 83000, the enzyme consists of two disulfide-linked dimers, wild-type enzyme and secreted recombinant enzyme, SDS-PAGE
250000 - 310000
300000
-
SDS-PAGE
390000
-
wild-type enzyme, gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
-
2 * 79000, intracellular human beta-glucuronidase in transfected BHK cells, SDS-PAGE
homotetramer
-
4 * 75000, SDS-PAGE
tetramer
additional information
-
the enzyme is composed of three components of 18000, 64000 and 80000 Da
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycoprotein
phosphoprotein
-
both the placental 80000 Da and 64000 Da peptides, though not the 18000 Da one, are apparently phosphorylated, whereas the enzyme of leukemic cells is poorly phosphorylated
proteolytic modification
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
55
-
depending on pH, substrate protects against inactivation
65
-
retains 90% of initial activity after 3 h at 65C
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Blue Sepharose FF column chromatography, phenyl-Sepharose high-Sub FF column chromatography, DEAE-Sephacel column chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in 3T3 fibroblasts and EJ carcinoma cells
-
expression vectors pMCG-GLUC and pMCG-dGLUC containing cDNA coding for human beta-glucuronidase and a C-terminal-truncated form of beta-glucuronidase respectively are transfected into BHK cells. The stable clones B702 expressing wild-type and B688 expressing mutant beta-glucuronidase. In the mutant enzyme a stop codon is introduced after the CAC/His-637 codon, thereby eliminating 14 amino acids from the C-terminus
-
wild-type and mutant enzymes expressed COS cells and GUSB-deficient fibroblasts from the SV40 late promoter in vector pJC119
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
D207A
-
4.9% of the wild-type activity is expressed in COS cells
E451A
-
0.6% of the wild-type activity is expressed in COS cells, tetrameric enzyme, ratio of turnover number to KM-value is decreased 9100fold as compared to wild-type enzyme. Mutant enzyme E541A is inactivated at a faster rate than the wild-type enzyme, and is completely inactivated within 30 min. 50 mM azide causes 70% loss of activity of wild-type enzyme and mutant enzyme E451A. 50 mM-0.5 M stimulates mutant enzyme E451A. 1 mM inhibits wild-type enzyme and mutant enzyme E451A
E451Q
-
5.9% of the wild-type activity is expressed in COS cells
E515A
-
no activity is expressed in COS cells
E540A
-
no activity is expressed in COS cells, tetrameric enzyme, ratio of turnover number to KM-value is decreased 33000 fold as compared to wild-type enzyme, optimal pH is 5.0 instead of 4.5 for the wild-type enzyme. Mutant enzyme is inactivated at a faster rate than the wild-type enzyme at 68C
E540D
-
no activity is expressed in COS cells
E540Q
-
0.3% of the wild-type activity is expressed in COS cells
Y504A
-
1.4% of the wild-type activity is expressed in COS cells, tetrameric enzyme, the ratio of turnover number to KM-value is decreased 830fold as compared to wild-type enzyme. Mutant enzyme is as stable as the wild-type enzyme at 68C
Y504F
-
2.3% of the wild-type activity is expressed in COS cells
Y504H
-
0.6% of the wild-type activity is expressed in COS cells
Y508A
-
no activity is expressed in COS cells
additional information
-
in the mutant enzyme a stop codon is introduced after the CAC/His-637 codon, thereby eliminating 14 amino acids from the C-terminus. Thereby the last Cys at position 644 is eliminated. In the mutant, covalent linkage between two monomers is no longer observed, indicating that Cys44 is involved in intermolecular disulfide-bond formation
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
diagnostics
-
beta-glucuronidase activity is a sensitive biomarker to assess low-level organophosphorus insecticide exposure, e.g. plasma BG activity for low-level organophosphorus-exposure compared to BChE activity, overview
medicine
nutrition
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crossover feeding trial in healthy women and men with a diet high in selected citrus fruit, crucifers and soy and a diet devoid of fruits, vegetables, and soy. Participants of the fruit and soy diet display a signifcantly higher beta-glucuronidase activity than those with the basal diet, where the enzyme activity decreased during the diet. Response to the diet does not differ by sex
toxicology
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measurement of beta-glucuronidase activity has no additive clinical value following a parathion overdose in humans