Information on EC 2.8.2.17 - chondroitin 6-sulfotransferase

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The expected taxonomic range for this enzyme is: Chordata

EC NUMBER
COMMENTARY hide
2.8.2.17
-
RECOMMENDED NAME
GeneOntology No.
chondroitin 6-sulfotransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
3'-phosphoadenylyl sulfate + chondroitin = adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
sulfate group transfer
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
chondroitin sulfate biosynthesis (late stages)
-
-
Glycosaminoglycan biosynthesis - chondroitin sulfate / dermatan sulfate
-
-
SYSTEMATIC NAME
IUBMB Comments
3'-phosphoadenylyl-sulfate:chondroitin 6'-sulfotransferase
The sulfation is at the 6-position of N-acetylgalactosamine residues of chondroitin. Not identical with EC 2.8.2.5 chondroitin 4-sulfotransferase.
CAS REGISTRY NUMBER
COMMENTARY hide
37292-93-6
-
83589-04-2
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
calf
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Quail
-
-
Manually annotated by BRENDA team
carbohydrate sulfotransferase 3; gene C6st1
SwissProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
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 sulfate + chondroitin
adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate
show the reaction diagram
3'-phosphoadenylyl sulfate + chondroitin
adenosine 3',5'-bisphosphate + chondroitin 6-sulfate
show the reaction diagram
-
-
-
?
3'-phosphoadenylyl sulfate + DELTA4HexUAalpha(1->3)Galbeta(1->3)Galbeta(1->4)Xylbeta(1->O)-Ser
adenosine 3',5'-bisphosphate + DELTA4HexUAalpha(1->3)Gal(6S)beta(1->3)Gal(6S)beta(1->4)Xylbeta(1->O)-Ser
show the reaction diagram
-
24% of the activity with GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xyl-(Gly)Ser-(Gly-Glu)
-
-
?
3'-phosphoadenylyl sulfate + DELTA4HexUAalpha(1->3)GalNAc(4S)beta(1->4)GlcUAbeta(1->3)Gal(4S)beta(1->3)Galbeta(1->4)Xylbeta(1->O)-Ser
adenosine 3',5'-bisphosphate + DELTA4HexUAalpha(1->3)GalNAc(4S)beta(1->4)GlcUAbeta(1->3)Gal(4S)beta(1->3)Gal(6S)beta(1->4)Xylbeta(1->O)-Ser
show the reaction diagram
-
270% of the activity with GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xyl-(Gly)Ser-(Gly-Glu)
-
-
?
3'-phosphoadenylyl sulfate + DELTA4HexUAalpha(1->3)GalNAc(4S)beta(1->4)GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xylbeta(1->O)-Ser
adenosine 3',5'-bisphosphate + DELTA4HexUAalpha(1->3)GalNAc(4S)beta(1->4)GlcUAbeta(1->3)Gal(6S)beta(1->3)Gal(6S)beta(1->4)Xylbeta(1->O)-Ser
show the reaction diagram
-
260% of the activity with GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xyl-(Gly)Ser-(Gly-Glu)
-
-
?
3'-phosphoadenylyl sulfate + DELTA4HexUAalpha(1->3)GalNAc(6S)beta(1->4)GlcUAbeta(1->3)Gal-Gal(6S)beta(1->4)Xyl-ol
adenosine 3',5'-bisphosphate + DELTA4HexUAalpha(1->3)GalNAc(6S)beta(1->4)GlcUAbeta(1->3)Gal(6S)beta(1->3)Gal(6S)beta(1->4)Xyl-ol
show the reaction diagram
-
360% of the activity with GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xyl-(Gly)Ser-(Gly-Glu)
-
-
?
3'-phosphoadenylyl sulfate + DELTA4HexUAalpha(1->3)GalNAc(6S)beta(1->4)GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xyl(2P)-ol
adenosine 3',5'-bisphosphate + DELTA4HexUAalpha(1->3)GalNAc(6S)beta(1->4)GlcUAbeta(1->3)Gal(6S)beta(1->3)-Galbeta(1->4)Xyl(2P)-ol
show the reaction diagram
-
290% of the activity with GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xyl-(Gly)Ser-(Gly-Glu)
-
-
?
3'-phosphoadenylyl sulfate + DELTA4HexUAalpha(1->4)GlcNAc(6S)-GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xylbeta(1->O)-Ser
adenosine 3',5'-bisphosphate + DELTA4HexUAalpha(1->4)GlcNAc(6S)beta(1->3)GlcUAbeta(1->3)Gal(6S)beta(1->3)Gal(6S)beta(1->4)Xylbeta(1->O)-Ser
show the reaction diagram
-
17% of the activity with GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xyl-(Gly)Ser-(Gly-Glu)
-
-
?
3'-phosphoadenylyl sulfate + Galbeta(1->3)Galbeta(1->4)Xylbeta(1->O)-Ser
adenosine 3',5'-bisphosphate + Gal(6S)beta(1->3)Gal(6S)beta(1->4)Xylbeta(1->O)-Ser
show the reaction diagram
-
4% of the activity with GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xyl-(Gly)Ser-(Gly-Glu)
-
-
?
3'-phosphoadenylyl sulfate + GalNAcbeta(1->4)GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xylbeta(1->O)-Ser
adenosine 3',5'-bisphosphate + GalNAc(6S)beta(1->4)GlcUAbeta(1->3)Gal(6S)beta(1->3)Gal(6S)beta(1->4)Xylbeta(1->O)-Ser
show the reaction diagram
-
84% of the activity with GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xyl-(Gly)Ser-(Gly-Glu)
-
-
?
3'-phosphoadenylyl sulfate + GlcNAcalpha(1->4)GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xylbeta(1->O)-Ser
adenosine 3',5'-bisphosphate + GlcNAcalpha(1->4)GlcUAbeta(1->3)Gal(6S)beta(1->3)Gal(6S)beta(1->4)Xylbeta(1->O)-Ser
show the reaction diagram
-
2% of the activity with GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xyl-(Gly)Ser-(Gly-Glu)
-
-
?
3'-phosphoadenylyl sulfate + GlcUAbeta(1->3)Gal(4S)beta(1->3)Galbeta(1->4)Xylbeta(1->O)-Ser
adenosine 3',5'-bisphosphate + GlcUAbeta(1->3)Gal(4S)beta(1->3)Gal(6S)beta(1->4)Xylbeta(1->O)-Ser
show the reaction diagram
-
20% of the activity with GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xyl-(Gly)Ser-(Gly-Glu)
-
-
?
3'-phosphoadenylyl sulfate + GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xyl-(Gly)Ser-(Gly-Glu)
adenosine 3',5'-bisphosphate + GlcUAbeta(1->3)Gal(6S)beta(1->3)Gal(6S)beta(1->4)Xyl-(Gly)Ser-(Gly-Glu)
show the reaction diagram
-
-
-
-
?
3'-phosphoadenylyl sulfate + GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xylbeta(1->O)-Ser
adenosine 3',5'-bisphosphate + GlcUAbeta(1->3)Gal(6S)beta(1->3)Gal(6S)beta(1->4)Xylbeta(1->O)-Ser
show the reaction diagram
-
8% of the activity with GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xyl-(Gly)Ser-(Gly-Glu)
-
-
?
3'-phosphoadenylyl sulfate + GlcUAbeta(1->3)GalNAc(4S)beta(1->4)GlcUAbeta(1->3)Gal(4S)beta(1->3)Galbeta(1->4)Xylbeta(1->O)-Ser
adenosine 3',5'-bisphosphate + GlcUAbeta(1->3)GalNAc(4S)beta(1->4)GlcUAbeta(1->3)Gal(4S)beta(1->3)Gal(6S)beta(1->4)Xylbeta(1->O)-Ser
show the reaction diagram
-
250% of the activity with GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xyl-(Gly)Ser-(Gly-Glu)
-
-
?
3'-phosphoadenylyl sulfate + GlcUAbeta(1->3)GalNAcbeta(1->4)GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xylbeta(1->O)-Ser
adenosine 3',5'-bisphosphate + GlcUAbeta(1->3)GalNAc(6S)beta(1->3)GlcUAbeta(1->3)Gal(6S)beta(1->3)Gal(6S)beta(1->4)Xylbeta(1->O)-Ser
show the reaction diagram
-
130% of the activity with GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xyl-(Gly)Ser-(Gly-Glu)
-
-
?
3'-phosphoadenylyl sulfate + keratan sulfate
?
show the reaction diagram
-
-
-
?
3'-phosphoadenylylsulfate + 1-phospho-N-acetylgalactosamine 4-sulfate
adenosine 3',5'-bisphosphate + 1-phospho-N-acetylgalactosamine 4,6-bissulfate
show the reaction diagram
-
-
-
?
3'-phosphoadenylylsulfate + beta-benzyl N-acetylglucosamine
adenosine 3',5'-bisphosphate + beta-benzyl N-acetylglucosaminesulfate
show the reaction diagram
-
enzyme does not use alpha-or beta-benzyl N-acetylgalactosamine
-
-
?
3'-phosphoadenylylsulfate + chondroitin
adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate
show the reaction diagram
3'-phosphoadenylylsulfate + chondroitin 4-sulfate
adenosine 3',5'-bisphosphate + chondroitin 4,6-bissulfate
show the reaction diagram
3'-phosphoadenylylsulfate + chondroitin sulfate A
adenosine 3',5'-bisphosphate + ?
show the reaction diagram
-
6.2% of the activity with chondroitin
-
-
?
3'-phosphoadenylylsulfate + chondroitin sulfate C
adenosine 3',5'-bisphosphate + ?
show the reaction diagram
-
3% of the activity with chondroitin
-
-
?
3'-phosphoadenylylsulfate + chondroitin-derived oligosaccharides
?
show the reaction diagram
3'-phosphoadenylylsulfate + corneal keratan sulfate
?
show the reaction diagram
3'-phosphoadenylylsulfate + desulfated dermatan sulfate
adenosine 3',5'-bisphosphate + ?
show the reaction diagram
-
95% of the activity with chondroitin
-
-
?
3'-phosphoadenylylsulfate + N-acetylgalactosamine 4-sulfate
adenosine 3',5'-bisphosphate + N-acetylgalactosamine 4,6-bissulfate
show the reaction diagram
-
-
-
?
3'-phosphoadenylylsulfate + phenyl 2-acetamido-2-deoxy-4-O-sulfonato-D-galactopyranose
adenosine 3',5'-bisphosphate + phenyl 2-acetamido-2-deoxy-4,6-di-O-sulfonato-D-galactopyranose
show the reaction diagram
-
-
-
-
?
3'-phosphoadenylylsulfate + UDP-N-acetylgalactosamine 4-sulfate
adenosine 3',5'-bisphosphate + UDP-N-acetylgalactosamine 4,6-bissulfate
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
3'-phosphoadenylyl sulfate + chondroitin
adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate
show the reaction diagram
3'-phosphoadenylyl sulfate + chondroitin
adenosine 3',5'-bisphosphate + chondroitin 6-sulfate
show the reaction diagram
O88199
-
-
-
?
3'-phosphoadenylyl sulfate + keratan sulfate
?
show the reaction diagram
O88199
-
-
-
?
3'-phosphoadenylylsulfate + chondroitin
adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate
show the reaction diagram
3'-phosphoadenylylsulfate + chondroitin 4-sulfate
adenosine 3',5'-bisphosphate + chondroitin 4,6-bissulfate
show the reaction diagram
-
may play a role in synthesis of proteoglycans
-
-
?
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ba2+
-
stimulates chondroitin 6-sulfotransferase activity and keratan sulfate sulfotransferase activity
Co2+
-
good activator, stimulates chondroitin 6-sulfotransferase activity and keratan sulfate sulfotransferase activity
Sr2+
-
stimulates chondroitin 6-sulfotransferase activity and keratan sulfate sulfotransferase activity
Zn2+
-
can partially replace Mn2+ in activation
additional information
-
Ca2+ has no effect
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4-chloromercuribenzoate
-
1 mM
ADP
-
60% inhibition at 0.12 mM
CaCl2
-
90% inhibition at 5 mM
CoCl2
-
50% inhibition at 5 mM
EDTA
-
in absence of added metal ion
heparin
-
40% inhibition in the nanomolar range
MgCl2
-
40% inhibition at 5 mM
MnCl2
-
75% inhibition at 5 mM
phenyl 2-acetamido-2-deoxy-4-O-sulfonato-D-galactopyranose
-
competitive, 5 mM, 76% inhibition, specific
-
PNGase F
deglycosylation inactivates the enzyme
-
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Basic proteins
-
stimulate
-
Chondroitin sulfates
-
competitive inhibitors
histone
-
stimulates, optimum concentration: 0.5 mg/ml
lysozyme
poly-L-lysine
-
stimulates 2fold at 1.5 mg/ml
Polyamines
-
stimulate
-
protamine
spermidine
spermine
additional information
-
enzyme is present in supernatant and in particulate fraction, detergent activates indirectly by releasing enzyme into the medium
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00034 - 0.00417
3'-phosphoadenylyl sulfate
0.00011 - 0.0333
3'-phosphoadenylylsulfate
0.00076 - 0.15
Chondroitin
0.00049 - 0.038
chondroitin 4-sulfate
0.9
decasaccharide
-
derived from chondroitin
-
1.8
Desulfated chondroitin sulfate
-
pH 8.2, 37C
0.48
dodecasaccharide
-
derived from chondroitin
-
0.05
GlcUAbeta(1->3)GalNAc(4S)beta(1->4)GlcUAbeta(1->3)Gal(4S)beta(1->3)Galbeta(1->4)Xylbeta(1->O)-Ser
-
pH 6.8, 37C
5
hexasaccharide
-
derived from chondroitin
-
0.0029 - 0.005
Keratan sulfate
0.36
N-acetylgalactosamine 4-sulfate
-
pH 7, 37C
0.06
native chondroitin
-
pH 8.2, 37C
-
2.5
Octasaccharide
-
derived from chondroitin
-
0.027
UDP-N-acetylgalactosamine 4-sulfate
-
pH 7, 37C
additional information
additional information
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.98
phenyl 2-acetamido-2-deoxy-4-O-sulfonato-D-galactopyranose
-
pH 6.8, 37C
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0000002
recombinant truncated mutant enzyme in COS-7 cell extract
0.00000022
recombinant wild-type enzyme in COS-7 cell extract
0.0000005 - 0.0000011
-
wild-type activity in fibroblasts
0.000231
recombinant protein expressed in COS-7 cells
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 8.5
-
-
5.8
-
chondroitin 6-sulfotransferase activity
6
-
double pH-optimum: 100% at pH 6.0 and 65% at pH 7.3
6.2
-
keratan sulfate sulfotransferase activity
6.4
keratan sulfate sulfotransferase activity, assay at
7.3
-
double pH-optimum: 100% at pH 6.0 and 65% at pH 7.3
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4 - 9
-
pH 4.0: about 30% of activity maximum, pH 9.0: about 55% of activity maximum
additional information
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
-
Manually annotated by BRENDA team
stromal cells
Manually annotated by BRENDA team
-
embryo chondrocytes release enzyme into the cell culture medium
Manually annotated by BRENDA team
increased enzyme expression in mobile cells, downregulation accompanies declining mobility of Schwann cells as they engaged in the myelination of re-growing axons
Manually annotated by BRENDA team
-
from surgical disc procedures performed on individuals with herniated discs and degenerative disc disease
Manually annotated by BRENDA team
additional information
the C6st1 expression is upregulated GFAP-positive Schwann cells in an early phase of tissue reorganisation after nerve crush, overview
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
additional information
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
75000
glycolysated enzyme, SDS-PAGE
150000
-
gel filtration
160000
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
-
2 * 75000, SDS-PAGE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycoprotein
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
60
-
thermal inactivation
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
homogeneity
-
partial
recombinant wild-type and mutant FLAG-tagged C6ST-1s from COS-7 cells by anti-FLAG-tag immunoaffinity and wheat germ agglutinin affinity chromatography
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
C6ST-2 isozyme
gene C6st, expression of wild-type and mutant FLAG-tagged C6ST-1s in COS-7 cells, addition of tunicamycin completely abolishes N-glycosylation of the recombinant enzyme and enzyme activity, overview
gene C6st1, DNA and amino acid sequence determination and analysis, expression analysis and sequence comparison, expression of HIs-tagged full-length enzyme and truncated enzyme, lacking the N-terminal transmembrane domain but retaining the PAPS-binding sites and the catalytic domain, in COS-7 cells
gene CHST3, expression of Flag-tagged wild-type andmutant enzymes
-
gene CHST3, expression of wild-type enzyme and mutant L286P in COS-7 cells as soluble FLAG-tagged proteins
-
gene CHST3, gene structure, genotyping
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
L259P
-
naturally occuring mutation of CHST3 involved in enzyme deficiency and related disease
L286P
-
naturally occuring mutation of gene CHST3 causing the Spondyloepiphyseal dysplasia Omani type, almost inactive mutant, phenotype, overview
L307P
-
naturally occuring mutation of CHST3 involved in enzyme deficiency and related disease
R222W
-
naturally occuring mutation of CHST3 involved in enzyme deficiency and related disease
T141M
-
homozygous missense mutation leading to a reduction of C6ST-1 activity to 24-29% of the wild type enzyme, the naturally occuring missense mutation in exon 3 of gene CHST3 causes Omani-type spondyloepiphyseal dysplasia with cardiac involvement, phenotype with skeletal features, cardiac involvement including mitral, tricuspid and/or aortic regurgitations and type E brachydactyly, overview
N250S
site-directed mutagenesis, mutation of a putative N-glycosylation site, deletion of the fourth N-glycosylation site from the N-terminus of the enzyme inhibits production of the active C6ST-1, the mutant remains in the endoplasmic reticulum, while all other wild-type and mutant enzymes are located in the Golgi apparatus
N413S
site-directed mutagenesis, mutation of a putative N-glycosylation site, deletion of the fourth or sixth N-glycosylation site from the N-terminus of the enzyme inhibits production of the active C6ST-1
N457S
site-directed mutagenesis, mutation of a putative N-glycosylation site, deletion of the fifth N-glycosylation site from the N-terminus of the enzyme results in a marked loss of the keratan sulfate sulfotransferase activity
N63S
site-directed mutagenesis, mutation of a putative N-glycosylation site
N74S
site-directed mutagenesis, mutation of a putative N-glycosylation site
N96S
site-directed mutagenesis, mutation of a putative N-glycosylation site
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
-
missense mutation R304Q found in patients with a distinct form of spondyloepiphyseal dysplasia, SED Omani type, leads to complete loss of activity, resulting in significant reduction of both DELTAHexA-GalNAc(6S) and DELTAHexA(2S)-GalNAc(6S) and elevated levels of DELTAHexA-GalNAc(4S,6S). Defect in chondroitin sulfate chain sulfation results in chondrodysplasia with major involvement of the spine