Information on EC 2.8.2.33 - N-acetylgalactosamine 4-sulfate 6-O-sulfotransferase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.8.2.33
-
RECOMMENDED NAME
GeneOntology No.
N-acetylgalactosamine 4-sulfate 6-O-sulfotransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
3'-phospho-5'-adenylyl sulfate + [chondroitin]-4-O-sulfo-N-acetyl-D-galactosamine = adenosine 3',5'-bisphosphate + [chondroitin]-4,6-di-O-sulfo-N-acetyl-D-galactosamine
show the reaction diagram
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3'-phospho-5'-adenylyl sulfate + [dermatan]-4-O-sulfo-N-acetyl-D-galactosamine = adenosine 3',5'-bisphosphate + [dermatan]-4,6-di-O-sulfo-N-acetyl-D-galactosamine
show the reaction diagram
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-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
chondroitin sulfate biosynthesis (late stages)
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dermatan 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:[dermatan]-4-O-sulfo-N-acetyl-D-galactosamine 6-O-sulfotransferase
The enzyme is activated by divalent cations and reduced glutathione. The enzyme from human transfers sulfate to position 6 of both internal residues and non-reducing terminal GalNAc 4-sulfate residues of chondroitin sulfate and dermatan sulfate. Oligosaccharides derived from chondroitin sulfate also serve as acceptors but chondroitin sulfate E, keratan sulfate and heparan sulfate do not. Differs from EC 2.8.2.17, chondroitin 6-sulfotransferase, in being able to use both chondroitin and dermatan as effective substrates
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
C57BL/6 mice
UniProt
Manually annotated by BRENDA team
squid
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
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enzyme knockdown in Lewis lung carcinoma cells results in a reduction in the proportion of E-units in chondroitin sulfate chains, in adhesiveness to extracellular matrix adhesion molecules and in proliferation in vitro
metabolism
-
the enzyme is involved in chondroitin sulfate synthesis
physiological function
-
the enzyme is responsible for pulmonary metastasis
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 + 4-sulfated chondroitin pentasaccharide
adenosine 3',5'-bisphosphate + 4,6'-sulfated chondroitin pentasaccharide
show the reaction diagram
3'-phosphoadenylyl sulfate + 4-sulfated chondroitin trisaccharide
adenosine 3',5'-bisphosphate + 4,6'-sulfated chondroitin trisaccharide
show the reaction diagram
3'-phosphoadenylyl sulfate + chondroitin
adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate
show the reaction diagram
3'-phosphoadenylyl sulfate + chondroitin 4-sulfate
adenosine 3',5'-bisphosphate + chondroitin 4,6'-disulfate
show the reaction diagram
-
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major terminal sulfotransferase activity plus a minor interior sulfotransferase activity
-
?
3'-phosphoadenylyl sulfate + chondroitin A
adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate E
show the reaction diagram
3'-phosphoadenylyl sulfate + chondroitin C
adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate ED
show the reaction diagram
-
synthesis of a unique chondroitin sulfate containing E-D hybrid tetrasaccharide structure by the recombinant enzyme
-
-
?
3'-phosphoadenylyl sulfate + chondroitin sulfate A
adenosine 3',5'-bisphosphate + chondroitin sulfate A 6'-sulfate
show the reaction diagram
3'-phosphoadenylyl sulfate + chondroitin sulfate A
adenosine 3',5'-bisphosphate + chondroitin sulfate E
show the reaction diagram
-
-
-
-
?
3'-phosphoadenylyl sulfate + chondroitin sulfate C
adenosine 3',5'-bisphosphate + chondroitin sulfate C 6'-sulfate
show the reaction diagram
3'-phosphoadenylyl sulfate + chondroitin sulfate E
adenosine 3',5'-bisphosphate + chondroitin sulfate E 6'-sulfate
show the reaction diagram
0.5% of activity compared with 4-sulfated pentasaccharide
-
-
?
3'-phosphoadenylyl sulfate + dermatan sulfate
adenosine 3',5'-bisphosphate + 6'-sulfated dermatan sulfate
show the reaction diagram
3'-phosphoadenylyl sulfate + dermatan sulfate
adenosine 3',5'-bisphosphate + dermatan sulfate 6'-sulfate
show the reaction diagram
-
source pig skin
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-
?
3'-phosphoadenylyl sulfate + GalNAc(4SO4)-D-glucuronic acid-GalNAc(4SO4)
adenosine 3',5'-bisphosphate + GalNAc(4,6SO4)-D-glucuronic acid-GalNAc(4SO4)
show the reaction diagram
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-
-
-
?
3'-phosphoadenylyl sulfate + GalNAc(4SO4)-D-glucuronic acid-GalNAc(6SO4)
adenosine 3',5'-bisphosphate + GalNAc(4,6SO4)-D-glucuronic acid-GalNAc(6SO4)
show the reaction diagram
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-
-
-
?
3'-phosphoadenylyl sulfate + GalNAc(4SO4)-Glc(2SO4)-GalNAc(6SO4)
adenosine 3',5'-bisphosphate + GalNAc(4,6SO4)-Glc(2SO4)-GalNAc(6SO4)
show the reaction diagram
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acceptor is a derivative of chondroitin sulfate A
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-
?
3'-phosphoadenylyl sulfate + GlcAbeta1-3GalNAc(4-O-sulfate)
adenosine 3',5'-bisphosphate + GlcAbeta1-3GalNAc(4,6-O-disulfate)
show the reaction diagram
-
GlcAbeta1-3GalNAc(4,6-O-disulfate) units are synthesized through sulfation of GlcAbeta1-3GalNAc(4-O-sulfate) units by the enzyme
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-
?
3'-phosphoadenylyl sulfate + glucuronic acid-GalNAc(SO4)-glucuronic acid-GalNAc(SO4)
adenosine 3',5'-bisphosphate + ?
show the reaction diagram
-
-
-
-
?
3'-phosphoadenylyl sulfate + keratan
adenosine 3',5'-bisphosphate + keratan 6'-sulfate
show the reaction diagram
0.3% of activity compared with 4-sulfated pentasaccharide
-
-
?
3'-phosphoadenylyl sulfate + phenyl 2-acetamido-2-deoxy-beta-D-galactopyranoside 4-O-sulfate
adenosine 3',5'-bisphosphate + phenyl 2-acetamido-2-deoxy-beta-D-galactopyranoside 4,6-O-disulfate
show the reaction diagram
-
-
-
-
?
3'-phosphoadenylyl sulfate + UDP-GalNAc 4-sulfate
adenosine 3',5'-bisphosphate + UDP-GalNAc-4,6-disulfate
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 A
adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate E
show the reaction diagram
3'-phosphoadenylyl sulfate + chondroitin sulfate A
adenosine 3',5'-bisphosphate + chondroitin sulfate E
show the reaction diagram
-
-
-
-
?
3'-phosphoadenylyl sulfate + GlcAbeta1-3GalNAc(4-O-sulfate)
adenosine 3',5'-bisphosphate + GlcAbeta1-3GalNAc(4,6-O-disulfate)
show the reaction diagram
-
GlcAbeta1-3GalNAc(4,6-O-disulfate) units are synthesized through sulfation of GlcAbeta1-3GalNAc(4-O-sulfate) units by the enzyme
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?
additional information
?
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Q7LFX5
the enzyme is responsible for biosynthesis of chondroitin sulfate E, CS-E plays important roles in numerous biological events, such as neurite outgrowth, overview, in colorectal cancer cells, the enzyme plays a minor role in tumor progression
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1R,3R,4S)-menthyl 2-acetamido-2-deoxy-4-O-sulfonato-beta-D-galactopyranoside
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(1S,3S,4R)-menthyl 2-acetamido-2-deoxy-4-O-sulfonato-beta-D-galactopyranoside
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weak inhibition
1-naphthyl 2-acetamido-2-deoxy-4-O-sulfonato-beta-D-galactopyranoside
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17beta-hydroxyestra-1,3,5(10)-trien-3-yl 2-acetamido-2-deoxy-4-O-sulfonato-beta-D-galactopyranoside
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competitive inhibitor, 40% inhibition at 0.05 mM, nearly complete inhibition at 0.25 mM
3-hydroxyestra-1,3,5(10)-trien-17beta-yl 2-acetamido-2-deoxy-4-O-sulfonato-beta-D-galactopyranoside
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4-chlorophenyl 2-acetamido-2-deoxy-4-O-sulfonato-beta-D-galactopyranoside
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4-fluorophenyl 2-acetamido-2-deoxy-4-O-sulfonato-beta-D-galactopyranoside
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4-nitrophenyl 2-acetamido-2-deoxy-4-O-sulfonato-beta-D-galactopyranoside
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benzyl 2-acetamido-2-deoxy-4-O-sulfonato-beta-D-galactopyranoside
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beta-O-phenyl-GalNAc(4SO4)
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inhibition of the enzyme in vitro
cholesteryl 2-acetamido-2-deoxy-4-O-sulfonato-beta-D-galactopyranoside
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cyclohexyl 2-acetamido-2-deoxy-4-O-sulfonato-beta-D-galactopyranoside
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octyl 2-acetamido-2-deoxy-4-O-sulfonato-beta-D-galactopyranoside
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phenyl 2-acetamido-2-deoxy-1-seleno-4-O-sulfonato-beta-D-galactopyranoside
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phenyl 2-acetamido-2-deoxy-4-O-sulfonato-1-thio-beta-D-galactopyranoside
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phenyl 2-acetamido-2-deoxy-beta-D-galactopyranoside 4-O-sulfate
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competitive, 5 mM, 24% residual activity
phenyl-beta-D-GalNAc(4SO4)
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additional information
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not inhibited by cyclohexyl 2-acetamido-2,6-dideoxy-4-O-sulfonato-beta-D-galactopyranoside
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Ba2+
squid
-
2.5 to 3.5fold activation
Ca2+
squid
-
2.5 to 3.5fold activation
CaCl2
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5 mM, 2.5 fold stimulation of interior sulfotransferase activity, 1.9 fold stimulation of terminal sulfotransferase activity
Co2+
squid
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2.5 to 3.5fold activation
KCl
squid
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2fold activation
Mg2+
squid
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2.5 to 3.5fold activation
Mn2+
squid
-
2.5 to 3.5fold activation
NaCl
squid
-
2fold activation
protamine
squid
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2fold activation
retinoic acid
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upregulation of GALNAC4S-6ST
Sr2+
squid
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2.5 to 3.5fold activation
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0005
3'-phosphoadenylyl sulfate
squid
-
pH 6.8, 25C
0.027
chondroitin sulfate
-
pH 6.9
0.0011
chondroitin sulfate A
squid
-
pH 6.8, 25C
0.0013
dermatan sulfate
squid
-
pH 6.8, 25C
0.028
GalNAc(4SO4)-D-glucuronic acid-GalNAc(4SO4)
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pH 6.8, 37C
0.82
GalNAc(4SO4)-D-glucuronic acid-GalNAc(6SO4)
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pH 6.8, 37C
0.013
GalNAc(4SO4)-Glc(2SO4)-GalNAc(6SO4)
-
pH 6.8, 37C
0.0038
UDP-GalNAc 4-sulfate
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pH 5.2
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.008
17beta-hydroxyestra-1,3,5(10)-trien-3-yl 2-acetamido-2-deoxy-4-O-sulfonato-beta-D-galactopyranoside
-
in imidazole-HCl, pH 6.8, at 37C
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.25
4-chlorophenyl 2-acetamido-2-deoxy-4-O-sulfonato-beta-D-galactopyranoside
Homo sapiens
-
in imidazole-HCl, pH 6.8, at 37C
2.5
phenyl-beta-D-GalNAc(4SO4)
Homo sapiens
-
in imidazole-HCl, pH 6.8, at 37C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0022
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substrate UDP-GalNAc 4-sulfate, pH 5.2
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.2
squid
-
-
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
20
-
assay at
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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in B cells, the enzyme acts as a B-cell receptor or coreceptor
Manually annotated by BRENDA team
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the expression GalNAc4S-6ST increases during differentiation from bone marrow cells to bone marrow-derived mast cells, the expression in bone marrow-derived mast cells is 3fold higher, than the expression in bone marrow cells
Manually annotated by BRENDA team
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the expression of GalNAc4S-6ST decreases during postnatal development
Manually annotated by BRENDA team
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mucosa cells, enzyme expression analysis by real-time RT-PCR and in situ hybridization in formalin-fixed and paraffin-embedded tissue sections, comparison to cancer tissue
Manually annotated by BRENDA team
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samples from 40 patients, enzyme expression analysis by real-time RT-PCR and in situ hybridization in formalin-fixed and paraffin-embedded tissue sections, comparison to healthy tissue
Manually annotated by BRENDA team
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of the external and the internal granular layer
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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inhibitory interneuron
Manually annotated by BRENDA team
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of mouse embryo
Manually annotated by BRENDA team
-
cortical neuron
Manually annotated by BRENDA team
-
low level of expression
Manually annotated by BRENDA team
-
highest expression
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
the enzyme is principally Golgi associated, a small portion of the enzyme is located at the cell surface
Manually annotated by BRENDA team
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cell matrix, SKOV-3 cell
Manually annotated by BRENDA team
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B-cell
-
Manually annotated by BRENDA team
-
OVCAR-3 cell
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
63000
squid
-
1 * 63000, SDS-PAGE
66000
squid
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
squid
-
1 * 63000, SDS-PAGE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycoprotein
squid
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contains N-linked oligosaccharides
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
-
squid
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recombinant FLAG-tagged GalNAc4S-6ST from COS-7 cells by anti-FLAG immunoaffinity chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
enzyme expression pattern during early mouse embryonic development, overview
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expressed in Rattus norvegicus chondrosarcoma LTC cells
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expression analysis
expression of FLAG-tagged GalNAc4S-6ST in COS-7 cells
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quantitative expression analysis and mRNA preparation using paraffin-embedded tissue samples, overview
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
N-acetylgalactosamine 4-sulfate 6-O-sulfotransferase mRNA is frequently detected in astrocytic tumors
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
synthesis
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use of enzyme for synthesis of chondroitin sulfate E from chondroitin sulfate A and of oversulfated dermatan sulfate with defined proportions of 4,6-sulfated residues