Information on EC 2.8.2.34 - glycochenodeoxycholate sulfotransferase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.8.2.34
-
RECOMMENDED NAME
GeneOntology No.
glycochenodeoxycholate sulfotransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
3'-phosphoadenylyl sulfate + glycochenodeoxycholate = adenosine 3',5'-bisphosphate + glycochenodeoxycholate 7-sulfate
show the reaction diagram
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.
CAS REGISTRY NUMBER
COMMENTARY hide
72668-90-7
-
72668-90.7
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
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
3'-phosphoadenylyl 5'-phosphosulfate + 3beta-hydroxy-5beta-cholanoic acid
adenosine 3',5'-bisphosphate + 3beta-hydroxy-5beta-cholanoic acid 3-sulfate
show the reaction diagram
-
-
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + 7-hydroxymethyl-12-methylbenz[a]anthracene
adenosine 3',5'-bisphosphate + ?
show the reaction diagram
-
bioactivation to an electrophilic sulfuric acid ester metabolite
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + chenodeoxycholate
adenosine 3',5'-bisphosphate + chenodeoxycholate 3-sulfate
show the reaction diagram
-
low activity
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + cortisol
adenosine 3',5'-bisphosphate + ?
show the reaction diagram
-
low activity
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + dehydroepiandrosterone
adenosine 3',5'-bisphosphate + dehydroepiandrosterone 3-sulfate
show the reaction diagram
3'-phosphoadenylyl 5'-phosphosulfate + deoxycholate
adenosine 3',5'-bisphosphate + deoxycholate 3-sulfate
show the reaction diagram
-
i.e. 3alpha,12alpha-dihydroxy-5beta-cholan-24-oic acid, low activity
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + estradiol
adenosine 3',5'-bisphosphate + ?
show the reaction diagram
3'-phosphoadenylyl 5'-phosphosulfate + estrone
adenosine 3',5'-bisphosphate + estrone 7-sulfate
show the reaction diagram
-
-
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + glycochenodeoxycholate
adenosine 3',5'-bisphosphate + ?
show the reaction diagram
3'-phosphoadenylyl 5'-phosphosulfate + glycodeoxycholate
adenosine 3',5'-bisphosphate + ?
show the reaction diagram
-
-
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + glycolithocholate
adenosine 3',5'-bisphosphate + glycolithocholate 3-sulfate
show the reaction diagram
3'-phosphoadenylyl 5'-phosphosulfate + lithocholate
adenosine 3',5'-bisphosphate + lithocholate 3-sulfate
show the reaction diagram
3'-phosphoadenylyl 5'-phosphosulfate + phenol
adenosine 3',5'-bisphosphate + phenyl sulfate
show the reaction diagram
-
-
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + taurochenodeoxycholate
adenosine 3',5'-bisphosphate + ?
show the reaction diagram
-
low activity
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + taurodeoxycholate
adenosine 3',5'-bisphosphate + ?
show the reaction diagram
-
-
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + taurolithocholate
adenosine 3',5'-bisphosphate + taurolithocholate 3-sulfate
show the reaction diagram
3'-phosphoadenylyl 5'-phosphosulfate + testosterone
adenosine 3',5'-bisphosphate + ?
show the reaction diagram
-
low activity
-
-
?
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
3'-phosphoadenylyl 5'-phosphosulfate + dehydroepiandrosterone
adenosine 3',5'-bisphosphate + dehydroepiandrosterone 3-sulfate
show the reaction diagram
-
-
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + glycochenodeoxycholate
adenosine 3',5'-bisphosphate + ?
show the reaction diagram
-
-
-
-
?
3'-phosphoadenylyl 5'-phosphosulfate + lithocholate
adenosine 3',5'-bisphosphate + lithocholate 3-sulfate
show the reaction diagram
-
-
-
-
?
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
NaCl
-
induces aggregation of the purified enzyme at 0.5 M
additional information
-
activity is independent of ionic strength in the range of 25-125 mM
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
3,6-dioxo-5alpha-cholanoate
-
-
3,6-dioxo-5beta-cholanoate
-
-
3,7-dioxo-5beta-cholanoate
-
-
3-oxo-5beta-cholanic acid
-
80-90% inhibition at equimolar amounts
3alpha,6beta-dihydroxy-5beta-cholanoate
-
-
5alpha-dihydrotestosterone
-
inhibits the hepatic enzyme in sham-operated and castrated male rats, prevents activation by 6-methylene-4-pregnene-3,20-dione
6-oxolithocholate
-
-
7-oxolithocholate
-
-
adenosine 3',5'-bisphosphate
-
potent, competitive inhibition
chenodeoxycholate
glycolithocholate
-
competitive, 50% inhibition at 0.04 mM
hyodeoxycholate
-
-
lithocholate
-
substrate inhibition
ursodeoxycholate
additional information
-
no inhibition by 3,12-dioxo-5beta-cholanoate
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
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
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00024
3beta-hydroxy-5beta-cholanoic acid
-
pH 6.5, 37C, 5 mM MgCl2
0.00072
dehydroepiandrosterone
-
pH 6.5, 37C, 5 mM MgCl2
0.00023 - 0.317
glycochenodeoxycholate
0.0016
lithocholate
-
-
additional information
additional information
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.26
3-oxo-5beta-cholanic acid
-
pH 6.5, 37C, 5 mM MgCl2
0.071
chenodeoxycholate
-
pH 7.0, 37C
0.018
glycolithocholate
-
pH 7.0, 37C
0.083 - 0.1
ursodeoxycholate
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0000006
-
male rat liver cytosol, substrate 7-hydroxymethyl-12-methylbenz[a]anthracene
0.000003
-
adrenal gland supernatant fraction
0.000004
-
proximal intestine supernatant fraction, female hamster
0.000005
-
proximal intestine supernatant fraction, male hamster
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
0.000023
-
sham-operated male rats, hepatic enzyme
0.000056
-
sham-operated male rats with 6-methylene-4-pregnene-3,20-dione, hepatic enzyme
0.00006
-
castrated male rats, hepatic enzyme
0.000062
-
liver supernatant fraction, female hamster
0.000083
-
castrated male rats with 6-methylene-4-pregnene-3,20-dione, hepatic enzyme
0.000094
-
purified enzyme, substrate glycolithocholate
0.000831
-
purified enzyme, substrate estradiol
0.018
-
purified enzyme
0.0187
-
purified enzyme
0.023
-
purified enzyme from femal rat liver
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.1
-
chromatofocusing
5.3
-
isoelectric focusing
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
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
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
29500
-
x * 29500, SDS-Page
30000
-
x * 30000, SDS-PAGE
32500
-
gel filtration
65000
-
x * 65000, SDS-PAGE
additional information
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
20% glycerol stabilizes
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C, hepatic and intestinal supernatant fractions, completely stable for at least 6 months
-
4C, 0.1 mg/ml purified enzyme, 3 weeks, no loss of activity
-
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
-
partially from liver by ion exchange chromatography
-
Renatured/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
redissolvation after precipitation with 1-6 M urea
-