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Information on EC 2.8.2.34 - glycochenodeoxycholate sulfotransferase
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EC Tree
2.8.2.34 glycochenodeoxycholate sulfotransferaseIUBMB Comments
The enzyme specifically sulfates glycochenodeoxycholate at the 7alpha-position (see also EC 2.8.2.14 bile-salt sulfotransferase). The monohydroxy bile acids glycolithocholate, chenodeoxycholate and ursodeoxycholate act as inhibitors.
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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Reaction Schemes
Synonyms
bile acid sulfotransferase, hydroxysteroid/bile acid sulfotransferase, bile acid:3'phosphoadenosine-5'phosphosulfate:sulfotransferase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
BAST
bile acid sulfotransferase
additional information
-
the enzyme is identical with the hydrosteroid sulfotransferase 2
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
3'-phosphoadenylyl sulfate + glycochenodeoxycholate = adenosine 3',5'-bisphosphate + glycochenodeoxycholate 7-sulfate
3'-phosphoadenylyl sulfate + glycochenodeoxycholate = adenosine 3',5'-bisphosphate + glycochenodeoxycholate 7-sulfate
-
-
-
-
3'-phosphoadenylyl sulfate + glycochenodeoxycholate = adenosine 3',5'-bisphosphate + glycochenodeoxycholate 7-sulfate
the enzyme is identical with the hydrosteroid sulfotransferase 2
-
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SYSTEMATIC NAME
IUBMB Comments
3'-phosphoadenylyl-sulfate:glycochenodeoxycholate 7-sulfotransferase
The enzyme specifically sulfates glycochenodeoxycholate at the 7alpha-position (see also EC 2.8.2.14 bile-salt sulfotransferase). The monohydroxy bile acids glycolithocholate, chenodeoxycholate and ursodeoxycholate act as inhibitors.
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CAS REGISTRY NUMBER
COMMENTARY
72668-90-7
-
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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
3'-phosphoadenylyl 5'-phosphosulfate + 3beta-hydroxy-5beta-cholanoic acid
adenosine 3',5'-bisphosphate + 3beta-hydroxy-5beta-cholanoic acid 3-sulfate
-
-
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + 7-hydroxymethyl-12-methylbenz[a]anthracene
adenosine 3',5'-bisphosphate + ?
-
bioactivation to an electrophilic sulfuric acid ester metabolite
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + chenodeoxycholate
adenosine 3',5'-bisphosphate + chenodeoxycholate 3-sulfate
-
low activity
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + cortisol
adenosine 3',5'-bisphosphate + ?
-
low activity
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + dehydroepiandrosterone
adenosine 3',5'-bisphosphate + dehydroepiandrosterone 3-sulfate
3'-phosphoadenylyl 5'-phosphosulfate + deoxycholate
adenosine 3',5'-bisphosphate + deoxycholate 3-sulfate
-
i.e. 3alpha,12alpha-dihydroxy-5beta-cholan-24-oic acid, low activity
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + estrone
adenosine 3',5'-bisphosphate + estrone 7-sulfate
-
-
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + glycochenodeoxycholate
adenosine 3',5'-bisphosphate + ?
3'-phosphoadenylyl 5'-phosphosulfate + glycodeoxycholate
adenosine 3',5'-bisphosphate + ?
-
-
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + glycolithocholate
adenosine 3',5'-bisphosphate + glycolithocholate 3-sulfate
3'-phosphoadenylyl 5'-phosphosulfate + lithocholate
adenosine 3',5'-bisphosphate + lithocholate 3-sulfate
3'-phosphoadenylyl 5'-phosphosulfate + phenol
adenosine 3',5'-bisphosphate + phenyl sulfate
-
-
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + taurochenodeoxycholate
adenosine 3',5'-bisphosphate + ?
-
low activity
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + taurodeoxycholate
adenosine 3',5'-bisphosphate + ?
-
-
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + taurolithocholate
adenosine 3',5'-bisphosphate + taurolithocholate 3-sulfate
3'-phosphoadenylyl 5'-phosphosulfate + testosterone
adenosine 3',5'-bisphosphate + ?
-
low activity
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + dehydroepiandrosterone
adenosine 3',5'-bisphosphate + dehydroepiandrosterone 3-sulfate
-
i.e. androst-5-ene-3beta-ol-17-one
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + dehydroepiandrosterone
adenosine 3',5'-bisphosphate + dehydroepiandrosterone 3-sulfate
-
-
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + dehydroepiandrosterone
adenosine 3',5'-bisphosphate + dehydroepiandrosterone 3-sulfate
-
i.e. androst-5-ene-3beta-ol-17-one
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + dehydroepiandrosterone
adenosine 3',5'-bisphosphate + dehydroepiandrosterone 3-sulfate
-
i.e. androst-5-ene-3beta-ol-17-one, best substrate
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + estradiol
adenosine 3',5'-bisphosphate + ?
-
-
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + estradiol
adenosine 3',5'-bisphosphate + ?
-
low activity
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + estradiol
adenosine 3',5'-bisphosphate + ?
-
-
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + glycochenodeoxycholate
adenosine 3',5'-bisphosphate + ?
-
-
product identification
-
?
3'-phosphoadenylyl 5'-phosphosulfate + glycochenodeoxycholate
adenosine 3',5'-bisphosphate + ?
-
low activity
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + glycolithocholate
adenosine 3',5'-bisphosphate + glycolithocholate 3-sulfate
-
-
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + glycolithocholate
adenosine 3',5'-bisphosphate + glycolithocholate 3-sulfate
-
low activity
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + glycolithocholate
adenosine 3',5'-bisphosphate + glycolithocholate 3-sulfate
-
i.e. N-(3-hydroxy-5beta-cholanoyl)glycine
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + glycolithocholate
adenosine 3',5'-bisphosphate + glycolithocholate 3-sulfate
-
-
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + lithocholate
adenosine 3',5'-bisphosphate + lithocholate 3-sulfate
-
-
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + lithocholate
adenosine 3',5'-bisphosphate + lithocholate 3-sulfate
-
low activity
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + taurolithocholate
adenosine 3',5'-bisphosphate + taurolithocholate 3-sulfate
-
-
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + taurolithocholate
adenosine 3',5'-bisphosphate + taurolithocholate 3-sulfate
-
low activity
-
-
?
additional information
?
-
-
the sulfation reaction may be a protective mechanism against the hepatotoxic effects of some bile acids in facilitating the excretion
-
-
?
additional information
?
-
-
poor activity with ursodeoxycholate and chenodeoxycholate, enzyme shows quite strict substrate specificity
-
-
?
additional information
?
-
-
substrate specificity of enzyme purified in different ways, overview
-
-
?
additional information
?
-
-
the enzyme is involved in prevention of toxicity of monohydroxy bile acids
-
-
?
additional information
?
-
-
substrate specificity, enzyme is most active with bile acids or steroids possessing a 3beta-hydroxy group and a 5-6 double bond or a trans A-B ring junction at the steroid nucleus, poor or no activity with cholate and conjugates, ursodeoxycholate, hyodeoxycholate, 3alpha,6alpha-dihydroxy-5beta-cholanoate, overview
-
-
?
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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
3'-phosphoadenylyl 5'-phosphosulfate + dehydroepiandrosterone
adenosine 3',5'-bisphosphate + dehydroepiandrosterone 3-sulfate
-
-
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + glycochenodeoxycholate
adenosine 3',5'-bisphosphate + ?
-
-
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + lithocholate
adenosine 3',5'-bisphosphate + lithocholate 3-sulfate
-
-
-
-
?
additional information
?
-
-
the sulfation reaction may be a protective mechanism against the hepatotoxic effects of some bile acids in facilitating the excretion
-
-
?
additional information
?
-
-
the enzyme is involved in prevention of toxicity of monohydroxy bile acids
-
-
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
additional information
-
activity is independent of ionic strength in the range of 25-125 mM
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
5alpha-dihydrotestosterone
-
inhibits the hepatic enzyme in sham-operated and castrated male rats, prevents activation by 6-methylene-4-pregnene-3,20-dione
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
6-methylene-4-pregnene-3,20-dione
-
activates the hepatic enzyme in sham-operated and castrated male rats, effect is counteracted by 5alpha-dihydrotestosterone
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.00023
glycochenodeoxycholate
-
male hamster, pH 7.0, 37°C, physiological substrate concentration
0.00142
glycochenodeoxycholate
-
female hamster, pH 7.0, 37°C, physiological substrate concentration
0.079
glycochenodeoxycholate
-
female hamster, pH 7.0, 37°C, saturating substrate concentration
0.317
glycochenodeoxycholate
-
male hamster, pH 7.0, 37°C, saturating substrate concentration
additional information
additional information
-
hyperbolic kinetics, allosteric effect
-
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.0000006
-
male rat liver cytosol, substrate 7-hydroxymethyl-12-methylbenz[a]anthracene
0.000012
-
castrated male rats with 5alpha-dihydrotestosterone, hepatic enzyme
0.000017
0.000019
-
sham-operated male rats with 5alpha-dihydrotestosterone and 6-methylene-4-pregnene-3,20-dione, hepatic enzyme
0.00002
-
female rat liver cytosol, substrate 7-hydroxymethyl-12-methylbenz[a]anthracene
0.000056
-
sham-operated male rats with 6-methylene-4-pregnene-3,20-dione, hepatic enzyme
0.000083
-
castrated male rats with 6-methylene-4-pregnene-3,20-dione, hepatic enzyme
0.000017
-
sham-operated male rats with 5alpha-dihydrotestosterone, hepatic enzyme
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.5
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
37
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pI VALUE
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
-
no activity in herat, spleen, skeletal muscle, brain, distal small intestine, and large intestine, activity is higher in femal than in male hamsters
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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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). ST2A8_MOUSE
282
0
33295
Swiss-Prot
other Location (Reliability: 2)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
additional information
-
enzyme appears in different aggregation forms, overview
additional information
-
the enzyme shows dfferent higher aggregation forms
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
monomer
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, hepatic and intestinal supernatant fractions, completely stable for at least 6 months
-
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
157fold by ultracentrifugation, ion exchange chromatography, and adenosine 3',5'-bisphosphate affinity chromatpgraphy
-
by ultracentrifugation, over 75fold by affinity chromatography on PK1B monoclonal antibody resin, which is especially effective with enzyme from female rat livers, and ammonium sulfate precipitation
-
from foetal liver cytosol, 760fold, ion exchange chromatography, adenosine 3',5'-bisphosphate affinity chromatography, and gel filtration, overview
-
from liver, by gel filtration, affinity chromatography, chromatofocusing, and hydroxyapatite chromatography, to homogeneity
-
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RENATURED/Commentary
ORGANISM
UNIPROT
LITERATURE
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Takikawa, H.; Stolz, A.; Kaplowitz, N.
Purification of a 32.5 kDa monomeric sulfotransferase from rat liver with activity for bile acids and phenolic steroids
FEBS Lett.
207
193-197
1986
Rattus norvegicus
brenda
Collins, R.H.; Lack, L.; Killenberg, P.G.
Rat hepatic bile acid sulfotransferase: enzyme response to androgens and estrogens
Am. J. Physiol.
252
G276-G280
1987
Rattus norvegicus
brenda
McKinney, S.C.; Collins, R.H.; Killenberg, P.G.; Lack, L.
Effect of 6-methylene-4-pregnene-3,20-dione treatment on hepatic bile acid sulfotransferase activity in male rats
Biochem. Pharmacol.
35
1050-1052
1986
Rattus norvegicus
brenda
Maghsoudloo, M.; Higgins, M.J.P.; Murphy, G.M.
Purification of human fetal hepatic bile acid sulfotransferase (BAST)
Biochem. Soc. Trans.
20
167S
1992
Homo sapiens
brenda
Suckling, R.J.; Murphy, G.M.; Higgins, M.J.P.
Human liver bile acid sulfotransferase: characterization of the partially purified enzyme
Biochem. Soc. Trans.
21
447S
1993
Homo sapiens
brenda
Falany, C.N.; Wheeler, J.; Coward, L.; Keehan, D.; Falany, J.L.; Barnes, S.
Bioactivation of 7-hydroxymethyl-12-methylbenz[a]anthracene by rat liver bile acid sulfotransferase I
J. Biochem. Toxicol.
7
241-248
1992
Rattus norvegicus
brenda
Barnes, S.; Burhol, P.G.; Zander, R.; Haggstrom, G.; Settine, R.L.; Hirschowitz, B.I.
Enzymic sulfation of glycochenodeoxycholic acid by tissue fractions from adult hamsters
J. Lipid Res.
20
952-959
1979
Mesocricetus auratus
brenda
Barnes, S.; Buchina, E.S.; King, R.J.; McBurnett, T.; Taylor, K.B.
Bile acid sulfotransferase I from rat liver sulfates bile acids and 3-hydroxy steroids: purification, N-terminal amino acid sequence, and kinetic properties
J. Lipid Res.
30
529-540
1989
Rattus norvegicus
brenda
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