Information on EC 2.8.2.22 - aryl-sulfate sulfotransferase

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

EC NUMBER
COMMENTARY hide
2.8.2.22
-
RECOMMENDED NAME
GeneOntology No.
aryl-sulfate sulfotransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
an aryl sulfate + a phenol = a phenol + an aryl sulfate
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
sulfate group transfer
-
-
-
-
SYSTEMATIC NAME
IUBMB Comments
aryl-sulfate:phenol sulfotransferase
The enzyme, characterized from bacteria that colonize the human and mouse intestine, catalyses the transfer of a sulfate group from a phenol sulfate ester to other phenolic compounds. Activity is enhanced by Mg2+ and Mn2+ [1]. Unlike EC 2.8.2.9, tyrosine-ester sulfotransferase and EC 2.8.2.1, aryl sulfotransferase, the enzyme does not act on 3'-phosphoadenylyl sulfate or adenosine 3',5'-bisphosphate [1]. The level of sulfation of polyphenols depends on the positions of the hydroxyl groups [3-5]. Hydroxy groups of tyrosine residues in peptides such as angiotensin can also act as acceptors [2]. The reaction proceeds according to a ping pong bi bi mechanism [6].
CAS REGISTRY NUMBER
COMMENTARY hide
158254-86-5
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
SwissProt
Manually annotated by BRENDA team
IIIH
SwissProt
Manually annotated by BRENDA team
IIIH
SwissProt
Manually annotated by BRENDA team
K-12
-
-
Manually annotated by BRENDA team
K-12
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
K-36
-
-
Manually annotated by BRENDA team
K-36
-
-
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-naphthyl sulfate + phenol
2-naphthol + phenyl sulfate
show the reaction diagram
3'-phosphoadenylylsulfate + 4-methylumbelliferol
adenosine 3',5'-bisphosphate + 4-methylumbelliferyl sulfate
show the reaction diagram
3'-phosphoadenylylsulfate + 4-nitrophenol
adenosine 3',5'-bisphosphate + 4-nitrophenyl sulfate
show the reaction diagram
3'-phosphoadenylylsulfate + phenol
adenosine 3',5'-bisphosphate + phenyl sulfate
show the reaction diagram
4-acetylphenyl sulfate + phenol
4-acetylphenol + phenyl sulfate
show the reaction diagram
-
28% of the activity with 4-nitrophenyl sulfate
-
-
?
4-acetylphenyl sulfate + tyramine
4-(2-aminoethyl)phenyl sulfate + 4-acetylphenol
show the reaction diagram
-
best donor with tyramine as acceptor
-
-
?
4-methylumbelliferyl sulfate + phenol
4-methylumbelliferol + phenyl sulfate
show the reaction diagram
4-methylumbelliferyl sulfate + tyramine
4-(2-aminoethyl)phenyl sulfate + 4-methylumbelliferol
show the reaction diagram
-
-
-
-
?
4-nitrophenyl sulfate + (5S)-5'-O-(5-amino-5-deoxy-beta-D-ribofuranosyl)-5'-C-[(2S,5S,6S)-5-carboxy-6-(hexadecanoyloxy)-4-methyl-3-oxo-1,4-diazepan-2-yl]uridine
?
show the reaction diagram
4-nitrophenyl sulfate + 1-butanol
4-nitrophenol + butyl sulfate
show the reaction diagram
-
10% conversion in 7 days
-
-
?
4-nitrophenyl sulfate + 1-naphthol
4-nitrophenol + 1-napththyl sulfate
show the reaction diagram
-
50% activity compared to phenol
-
-
?
4-nitrophenyl sulfate + 1-octanol
4-nitrophenol + octyl sulfate
show the reaction diagram
-
10% conversion in 7 days
-
-
?
4-nitrophenyl sulfate + 1-pentanol
4-nitrophenol + pentyl sulfate
show the reaction diagram
-
10% conversion in 7 days
-
-
?
4-nitrophenyl sulfate + 1-phenylethanol
4-nitrophenol + 1-phenylethyl sulfate
show the reaction diagram
-
2-10% conversion in 7 days
-
-
?
4-nitrophenyl sulfate + 17beta-estradiol
4-nitrophenol + ?
show the reaction diagram
-
after 24 h about 80% of the 17beta-estradiol is converted
-
-
?
4-nitrophenyl sulfate + 2-aminophenol
4-nitrophenol + 2-aminophenyl sulfate
show the reaction diagram
-
136% activity compared to phenol
-
-
?
4-nitrophenyl sulfate + 2-butanol
4-nitrophenol + 2-butyl sulfate
show the reaction diagram
-
2-10% conversion in 7 days
-
-
?
4-nitrophenyl sulfate + 2-naphthol
4-nitrophenol + 2-napththyl sulfate
show the reaction diagram
-
86% activity compared to phenol
-
-
?
4-nitrophenyl sulfate + 2-octanol
4-nitrophenol + 2-octyl sulfate
show the reaction diagram
-
2-10% conversion in 7 days
-
-
?
4-nitrophenyl sulfate + 2-phenylethanol
4-nitrophenol + 2-phenylethyl sulfate
show the reaction diagram
-
50% conversion in 7 days
-
-
?
4-nitrophenyl sulfate + 3,5-dimethoxyphenol
4-nitrophenol + 3,5-dimethoxyphenyl sulfate
show the reaction diagram
-
33% activity compared to phenol
-
-
?
4-nitrophenyl sulfate + 3-chlorophenol
3-chlorophenyl sulfate + 4-nitrophenol
show the reaction diagram
4-nitrophenyl sulfate + 3-chlorophenol
4-nitrophenol + 3-chlorophenyl sulfate
show the reaction diagram
-
138% activity compared to phenol
-
-
?
4-nitrophenyl sulfate + 4-acetaminophen
4-nitrophenol + 4-acetaminophenylsulfate
show the reaction diagram
4-nitrophenyl sulfate + 4-aminophenol
4-nitrophenol + 4-aminophenyl sulfate
show the reaction diagram
-
102% activity compared to phenol
-
-
?
4-nitrophenyl sulfate + 4-chlorophenol
4-nitrophenol + 4-chlorophenyl sulfate
show the reaction diagram
-
195% activity compared to phenol
-
-
?
4-nitrophenyl sulfate + 4-cresol
4-nitrophenol + 4-cresol sulfate
show the reaction diagram
-
200% activity compared to phenol
-
-
?
4-nitrophenyl sulfate + 4-hydroxybenzoate
4-nitrophenol + 4-hydroxybenzoyl sulfate
show the reaction diagram
4-nitrophenyl sulfate + 4-hydroxybenzoic acid
?
show the reaction diagram
-
0.7% activity compared to phenol
-
-
?
4-nitrophenyl sulfate + 4-hydroxyindole
4-nitrophenol + indol-4-yl sulfate
show the reaction diagram
-
88% activity compared to phenol
-
-
?
4-nitrophenyl sulfate + 5-hydroxyindole
4-nitrophenol + indol-5-yl sulfate
show the reaction diagram
-
74% activity compared to phenol
-
-
?
4-nitrophenyl sulfate + 9-phenanthrol
9-phenanthroyl sulfate + 4-nitrophenol
show the reaction diagram
4-nitrophenyl sulfate + alpha-naphthol
4-nitrophenol + 1-napththyl sulfate
show the reaction diagram
4-nitrophenyl sulfate + benzyl alcohol
4-nitrophenol + benzyl sulfate
show the reaction diagram
-
10% conversion in 7 days
-
-
?
4-nitrophenyl sulfate + cholecystokinin-8
? + 4-nitrophenol
show the reaction diagram
4-nitrophenyl sulfate + cyclohexanol
4-nitrophenol + cyclohexyl sulfate
show the reaction diagram
-
10% conversion in 7 days
-
-
?
4-nitrophenyl sulfate + D-glucose
?
show the reaction diagram
-
2-10% conversion in 7 days
-
-
?
4-nitrophenyl sulfate + dihydroxyacetone
4-nitrophenol + ?
show the reaction diagram
-
2-10% conversion in 7 days
-
-
?
4-nitrophenyl sulfate + dopamine
4-nitrophenol + ?
show the reaction diagram
-
540% activity compared to phenol
-
-
?
4-nitrophenyl sulfate + dopamine
? + 4-nitrophenol
show the reaction diagram
-
-
-
-
?
4-nitrophenyl sulfate + enkephalin
? + 4-nitrophenol
show the reaction diagram
4-nitrophenyl sulfate + epinephrine
? + 4-nitrophenol
show the reaction diagram
4-nitrophenyl sulfate + estradiol
estradiol sulfate + 4-nitrophenol
show the reaction diagram
4-nitrophenyl sulfate + estrone
4-nitrophenol + estrone 3-sulfate
show the reaction diagram
-
after 24 h 90% of the estrone is sulfated
-
-
?
4-nitrophenyl sulfate + furfuryl alcohol
4-nitrophenol + furfuryl sulfate
show the reaction diagram
-
10% conversion in 7 days
-
-
?
4-nitrophenyl sulfate + glycerol
4-nitrophenol + ?
show the reaction diagram
-
10% conversion in 7 days
-
-
?
4-nitrophenyl sulfate + insulin
? + 4-nitrophenol
show the reaction diagram
4-nitrophenyl sulfate + isoquercetin
4-nitrophenol + isoquercetin 4'-O-sulfate
show the reaction diagram
-
i.e. quercetin 3-O-glucoside
-
-
?
4-nitrophenyl sulfate + kyotorphin
? + 4-nitrophenol
show the reaction diagram
4-nitrophenyl sulfate + Leu-enkephalin
4-nitrophenol + Leu-enkephalin sulfate
show the reaction diagram
-
within 48 h 91% of Leu-enkephalin is sulfated which reaches 98% after 6 days of incubation
-
-
?
4-nitrophenyl sulfate + N-hydroxysuccinimide
?
show the reaction diagram
-
2-10% conversion in 7 days
-
-
?
4-nitrophenyl sulfate + octyl glucoside
?
show the reaction diagram
-
2-10% conversion in 7 days
-
-
?
4-nitrophenyl sulfate + phenol
4-nitrophenol + phenyl sulfate
show the reaction diagram
4-nitrophenyl sulfate + phenol
phenyl sulfate + 4-nitrophenol
show the reaction diagram
4-nitrophenyl sulfate + phenolphthalein
phenolphthalein O-sulfate + 4-nitrophenol
show the reaction diagram
4-nitrophenyl sulfate + quercetin
4-nitrophenol + quercetin 3'-O-sulfate
show the reaction diagram
-
-
-
-
?
4-nitrophenyl sulfate + R-PYYYLQ
? + 4-nitrophenol
show the reaction diagram
4-nitrophenyl sulfate + resorcinol
4-nitrophenol + resorcinyl sulfate
show the reaction diagram
-
70% activity compared to phenol
-
-
?
4-nitrophenyl sulfate + resorcinol
resorcinol O-sulfate + 4-nitrophenol
show the reaction diagram
4-nitrophenyl sulfate + salicylamide
salicylamide O-sulfate + 4-nitrophenol
show the reaction diagram
4-nitrophenyl sulfate + taxifolin
4-nitrophenol + taxifolin 4'-O-sulfate
show the reaction diagram
-
i.e. 2,3-dihydroquercetin
-
-
?
4-nitrophenyl sulfate + trypsin inhibitor
? + 4-nitrophenol
show the reaction diagram
-
-
-
-
?
4-nitrophenyl sulfate + tyramine
4-(2-aminoethyl)phenyl sulfate + 4-nitrophenol
show the reaction diagram
4-nitrophenyl sulfate + tyramine
4-nitrophenol + 4-(2-aminoethyl)phenyl sulfate
show the reaction diagram
-
60% activity compared to phenol
-
-
?
4-nitrophenyl sulfate + tyramine
4-nitrophenol + tyramine sulfate
show the reaction diagram
4-nitrophenyl sulfate + tyrosine
4-nitrophenol + tyrosine sulfate
show the reaction diagram
4-nitrophenyl sulfate + tyrosine
tyrosine O-sulfate + 4-nitrophenol
show the reaction diagram
4-nitrophenyl sulfate + tyrosine methylester
O-sulfotyrosine methylester + 4-nitrophenol
show the reaction diagram
-
-
-
-
?
alpha-naphthyl sulfate + phenol
alpha-naphthol + phenyl sulfate
show the reaction diagram
an aryl sulfate + a phenol
a phenol + an aryl sulfate
show the reaction diagram
estrone sulfate + phenol
estrone + phenyl sulfate
show the reaction diagram
-
11% of the activity with p-nitrophenyl sulfate
-
-
?
hydroxyacylcaprazol E + a phenol
a phenol + hydroxyacylcaprazol E sulfate
show the reaction diagram
methylumbelliferone sulfate + phenol
methylumbelliferone + phenyl sulfate
show the reaction diagram
phenyl sulfate + an aryl alcohol
phenol + an aryl sulfate
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
4-nitrophenyl sulfate + phenol
4-nitrophenol + phenyl sulfate
show the reaction diagram
-
100% activity
-
-
?
an aryl sulfate + a phenol
a phenol + an aryl sulfate
show the reaction diagram
Q8FDI4
periplasmic ASST is an in vivo substrate of DsbL, the most reactive oxidizing thioredoxin-like protein known to date, ASST activity is detected only when both functional proteins DsbL and DsbI are coexpressed
-
-
?
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
adenosine 3',5'-bisphosphate
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Co2+
-
33% increase at 2 mM
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1-naphthyl sulfate
4-chloromercuribenzenesulfonic acid
-
50% inhibition at 0.0000038 mM
4-nitrophenol
acetone
-
in acetone the activity of the enzyme decreases to 30-34% of the original activity
ATP
-
non-competitive, enzyme is not phosphorylated but binds ATP
Ca2+
-
33% inhibition at 2 mM
Co2+
-
slight inhibition at 2 mM
diethyl dicarbonate
-
50% inhibition at 0.28 mM
dimethylformamide
-
in dimethylformamide the activity of the enzyme decreases to 30-34% of the original activity
dioxane
-
in dioxane the activity of the enzyme decreases to 30-34% of the original activity
diphosphate
-
non-competitive
DTNB
-
50% inhibition at 0.023 mM
Fe2+
-
50% inhibition at 0.6 mM
Hg2+
-
50% inhibition at 0.001 mM
N-tosyl-L-lysylchloromethane
-
50% inhibition at 0.04 mM
nucleotide triphosphates
-
non-competitive
-
Pb2+
-
35% inhibition at 2 mM
PCMB
-
50% inhibition at 0.000025 mM
Pentachlorophenol
-
50% inhibition at 0.0255 mM with tyramine as substrate
phenol
tetrahydrofuran
-
in tetrhydrofuran the activity of the enzyme decreases to 30-34% of the original activity
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Diethyldithiocarbamic acid sodium salt
-
-
-
EDTA
-
the addition of 0.1 mM EDTA increases product formation by 2.5fold
thioredoxin-like protein DsbL
besides the role of DsbL in the formation of the structural disulfide bond of ASST, it might improve the folding efficiency of ASST in vivo by preventing unspecific aggregation of ASST
-
tosyl-L-Lys chloromethyl ketone
-
-
additional information
-
disulfide bond required for activity
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0445
4-Methylumbelliferyl sulfate
at pH 8.0, at 25C
0.0481 - 0.163
4-nitrophenyl sulfate
0.0111
dopamine
-
recombinant protein
0.0345
methylumbelliferone sulfate
-
at pH 6.7, temperature not specified in the publication
0.0259 - 1.35
phenol
3.5
tyramine
-
with 4-nitrophenyl sulfate as second substrate, pH 8, 37C
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.14
4-nitrophenyl sulfate
-
at pH 6.7, temperature not specified in the publication
0.15
methylumbelliferone sulfate
-
at pH 6.7, temperature not specified in the publication
48.6
phenol
at pH 8.0, at 25C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.63 - 2.72
1-naphthyl sulfate
0.12 - 0.89
4-nitrophenol
0.45 - 0.66
ATP
0.2 - 0.7
diphosphate
0.048 - 46.1
phenol
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25.6
-
purified, recombinant, enterokinase-cleaved enzyme
37.1
-
purified recombinant enzyme
additional information
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8.5
-
phenol
10 - 10.5
-
-
additional information
-
optimal pH depends on acceptor substrate
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5 - 7.6
-
maximal activity is observed at pH 6.7 with half-maximal values at pH 5.0 and 7.6
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
9
-
calculated from amino acid sequence, isoelectric focussing
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
58000
-
x * 58000, SDS-PAGE
63765
2 * 63765, freshly purified enzyme, electrospray ionization mass spectrometry
63800
2 * 63800, X-ray crystallography
63880
-
calculated from nucleotide sequence
64000
-
SDS-PAGE, gel filtration, wild-type and mutant enzymes
71400
-
x * 71400, calculated from amino acid sequence
73000
-
2 * 73000, SDS-PAGE
128000
size-exclusion chromatography, homodimer
160000
-
gel filtration
290000
-
gel filtration
315000
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homodimer
monomer
tetramer
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 7
-
most stable pH for storage
645838
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
45
-
10 min, pH 5.5-7, 50% loss of activity
47
-
the melting temperature is at 47C
50
-
10 min, stable below
55
-
10 min, pH 5.5-7, complete loss of activity
60
-
10 min, inactivation
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
4-nitrophenyl sulfate, stabilizes against thermal inactivation and against inactivation on storage under cold conditions
-
ORGANIC SOLVENT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
2-pentanone
-
enzyme activity in biphasic systems with more polar solvents gets completely lost
acetonitrile
butyl acetate
-
enzyme activity in biphasic systems with more polar solvents gets completely lost
chloroform
cyclohexane
-
retains high enzyme activity in biphasic systems composed of water and nonpolar solvents
dimethyl formamide
-
enzyme tolerates presence of 10% of polar cosolvents but loses significant activity at higher solvent concentrations of 30-40%
DMSO
-
the enzyme is stable in the presence of 10% (v/v) of DMSO and even in 25% of DMSO, the remaining activity is still 733
Ethyl acetate
Methanol
methyl tert-butyl ether
-
enzyme activity in biphasic systems with more polar solvents gets completely lost
toluene
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4C or -20C, more than 50% loss of activity after 1 month
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
chromatography
homogeneity
-
nickel affinity column chromatography, and Superdex 200 gel filtration
-
Poros column chromatography and Q-FF column chromatography
-
purification using polyclonal antibodies
-
recombinant His-tagged enzyme from Escherichia coli strain BL21 (DE3) by treatement with enterokinase to exclude the DsbA and nickel affinity chromatography
-
recombinant protein
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Escherichia coli
-
expressed in Escherichia coli BL21(DE3)cells
-
expressed in Escherichia coli NM522
-
expressed in Escherichia coli Rosetta2 (DE3)pLys cells
-
expression in Escherichia coli K12
gene astA, cloned from a genomic library, DNA and amino acid sequence determination and analysis, subcloning in Escherichia coli strain TH2, expression of His-tagged enzyme in Escherichia coli strain BL21 (DE3)
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
C349S
-
5% of wild type activity
C349S/C445S
-
7% of wild type activity
C349S/C445S/C451S
-
7% of wild type activity
C349S/C451S
-
8% of wild type activity
C445S
-
24% of wild type activity
C445S/C451S
-
7% of wild type activity
C451S
-
94% of wild type activity
Y101F
-
reduced enzyme activity
Y123F
-
severely reduced enzyme activity
Y160F
-
reduced enzyme activity
Y389F
-
reduced enzyme activity
Y47F
-
reduced enzyme activity
Y494F
-
enzyme activity similar to wild-type enzyme
Y500F
-
reduced enzyme activity
Y515F
-
reduced enzyme activity
Y533F
-
reduced enzyme activity
Y82F
-
reduced enzyme activity
Y92F
-
increased enzyme activity
Y101F
-
reduced enzyme activity
-
Y123F
-
severely reduced enzyme activity
-
Y47F
-
reduced enzyme activity
-
Y82F
-
reduced enzyme activity
-
Y92F
-
increased enzyme activity
-
H180L
-
the mutant shows less than 5% activity compared to the wild type enzyme
H253L
-
the mutant shows less than 5% activity compared to the wild type enzyme
H308L
-
the mutant shows less than 5% activity compared to the wild type enzyme
H180L
-
the mutant shows less than 5% activity compared to the wild type enzyme
-
H253L
-
the mutant shows less than 5% activity compared to the wild type enzyme
-
H308L
-
the mutant shows less than 5% activity compared to the wild type enzyme
-
Show AA Sequence (243 entries)
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