Information on EC 2.8.2.17 - chondroitin 6-sulfotransferase and Organism(s) Homo sapiens

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The taxonomic range for the selected organisms is: Homo sapiens

The enzyme appears in selected viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.8.2.17
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RECOMMENDED NAME
GeneOntology No.
chondroitin 6-sulfotransferase
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
sulfate group transfer
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-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
chondroitin sulfate biosynthesis (late stages)
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Glycosaminoglycan biosynthesis - chondroitin sulfate / dermatan sulfate
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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
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83589-04-2
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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 + 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
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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
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270% of the activity with GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xyl-(Gly)Ser-(Gly-Glu)
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-
?
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
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260% of the activity with GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xyl-(Gly)Ser-(Gly-Glu)
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-
?
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
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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
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290% of the activity with GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xyl-(Gly)Ser-(Gly-Glu)
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?
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
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17% of the activity with GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xyl-(Gly)Ser-(Gly-Glu)
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-
?
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
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4% of the activity with GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xyl-(Gly)Ser-(Gly-Glu)
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-
?
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
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84% of the activity with GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xyl-(Gly)Ser-(Gly-Glu)
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-
?
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
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2% of the activity with GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xyl-(Gly)Ser-(Gly-Glu)
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?
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
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20% of the activity with GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xyl-(Gly)Ser-(Gly-Glu)
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?
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
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8% of the activity with GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xyl-(Gly)Ser-(Gly-Glu)
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?
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
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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
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130% of the activity with GlcUAbeta(1->3)Galbeta(1->3)Galbeta(1->4)Xyl-(Gly)Ser-(Gly-Glu)
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?
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
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?
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
-
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?
3'-phosphoadenylylsulfate + chondroitin sulfate A
adenosine 3',5'-bisphosphate + ?
show the reaction diagram
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6.2% of the activity with chondroitin
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?
3'-phosphoadenylylsulfate + chondroitin sulfate C
adenosine 3',5'-bisphosphate + ?
show the reaction diagram
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3% of the activity with chondroitin
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?
3'-phosphoadenylylsulfate + corneal keratan sulfate
?
show the reaction diagram
transfers sulfate to position 6 of Gal residues
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?
3'-phosphoadenylylsulfate + desulfated dermatan sulfate
adenosine 3',5'-bisphosphate + ?
show the reaction diagram
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95% of the activity with chondroitin
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?
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
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-
-
-
?
additional information
?
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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
additional information
?
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the enzyme mediates the sulfation of proteoglycans, particularly chondroitin sulfate, in the extracellular matrix of cartilage
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
phenyl 2-acetamido-2-deoxy-4-O-sulfonato-D-galactopyranose
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competitive, 5 mM, 76% inhibition, specific
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.038
chondroitin 4-sulfate
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pH 6.8, 37°C
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
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pH 6.8, 37°C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.98
phenyl 2-acetamido-2-deoxy-4-O-sulfonato-D-galactopyranose
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pH 6.8, 37°C
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0000005 - 0.0000011
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wild-type activity in fibroblasts
additional information
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.8
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assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
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assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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from surgical disc procedures performed on individuals with herniated discs and degenerative disc disease
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
C6ST-2 isozyme
gene CHST3, expression of Flag-tagged wild-type andmutant enzymes
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gene CHST3, expression of wild-type enzyme and mutant L286P in COS-7 cells as soluble FLAG-tagged proteins
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gene CHST3, gene structure, genotyping
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
L259P
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naturally occuring mutation of CHST3 involved in enzyme deficiency and related disease
L286P
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naturally occuring mutation of gene CHST3 causing the Spondyloepiphyseal dysplasia Omani type, almost inactive mutant, phenotype, overview
L307P
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naturally occuring mutation of CHST3 involved in enzyme deficiency and related disease
R222W
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naturally occuring mutation of CHST3 involved in enzyme deficiency and related disease
T141M
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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
additional information
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identification of eight naturally occuring CHST3 mutations in six unrelated individuals who presented at birth with congenital joint dislocations with diagnosis of either Larsen syndrome or humero-spinal dysostosis, the patients show reduced enzyme activity and congenital dislocation of the knees, elbow joint dysplasia with subluxation and limited extension, hip dysplasia or dislocation, clubfoot, short stature, and kyphoscoliosis developing in late childhood, genotyping, enzyme mutant phenotypes, overview
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
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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