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Information on EC 2.8.2.33 - N-acetylgalactosamine 4-sulfate 6-O-sulfotransferase and Organism(s) Homo sapiens and UniProt Accession Q7LFX5
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2.8.2.33 N-acetylgalactosamine 4-sulfate 6-O-sulfotransferaseIUBMB Comments
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
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Word Map
- 2.8.2.33
- chondroitin
- 5'-phosphosulfate
-
2-o-sulfotransferase
- 3'-phosphoadenosine
-
nonreducing
- glycosaminoglycans
-
sulfotransferases
- squid
-
6-sulfotransferase
-
uronyl
- trisaccharide
-
oversulfated
- midkine
- chondroitinase
- medicine
- synthesis
The taxonomic range for the selected organisms is: Homo sapiens
The enzyme appears in selected viruses and cellular organisms
The enzyme appears in selected viruses and cellular organisms
Reaction Schemes
+
=
+
+
=
+
Synonyms
galnac4s-6st, n-acetylgalactosamine 4-sulfate 6-o-sulfotransferase, galnac 4-sulfate 6-o-sulfotransferase, galnac(4s)-6-o-sulfotransferase, galnac4s6st, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
PATHWAY SOURCE
PATHWAYS
-
-, -
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
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 sulfate + 4-sulfated chondroitin pentasaccharide
adenosine 3',5'-bisphosphate + 4,6'-sulfated chondroitin pentasaccharide
best substrate, sulfation only with nonreducing terminal GalNAc(4-SO4) residues
-
-
?
3'-phosphoadenylyl sulfate + 4-sulfated chondroitin trisaccharide
adenosine 3',5'-bisphosphate + 4,6'-sulfated chondroitin trisaccharide
95.2% of activity compared with 4-sulfated pentasaccharide
-
-
?
3'-phosphoadenylyl sulfate + chondroitin
adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate
3'-phosphoadenylyl sulfate + chondroitin A
adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate E
synthesis of chondroitin sulfate E
-
-
?
3'-phosphoadenylyl sulfate + chondroitin sulfate A
adenosine 3',5'-bisphosphate + chondroitin sulfate A 6'-sulfate
33.7% of activity compared with 4-sulfated pentasaccharide
-
-
?
3'-phosphoadenylyl sulfate + chondroitin sulfate C
adenosine 3',5'-bisphosphate + chondroitin sulfate C 6'-sulfate
0.5% of activity compared with 4-sulfated pentasaccharide
-
-
?
3'-phosphoadenylyl sulfate + chondroitin sulfate E
adenosine 3',5'-bisphosphate + chondroitin sulfate E 6'-sulfate
0.5% of activity compared with 4-sulfated pentasaccharide
-
-
?
3'-phosphoadenylyl sulfate + dermatan sulfate
adenosine 3',5'-bisphosphate + 6'-sulfated dermatan sulfate
4.9% of activity compared with 4-sulfated pentasaccharide
-
-
?
3'-phosphoadenylyl sulfate + keratan
adenosine 3',5'-bisphosphate + keratan 6'-sulfate
0.3% of activity compared with 4-sulfated pentasaccharide
-
-
?
3'-phosphoadenylyl sulfate + chondroitin
adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate
3'-phosphoadenylyl sulfate + chondroitin 4-sulfate
adenosine 3',5'-bisphosphate + chondroitin 4,6'-disulfate
-
-
major terminal sulfotransferase activity plus a minor interior sulfotransferase activity
-
?
3'-phosphoadenylyl sulfate + chondroitin 4-sulfate
adenosine 3',5'-bisphosphate + chondroitin sulfate E
-
-
-
-
?
3'-phosphoadenylyl sulfate + chondroitin sulfate A
adenosine 3',5'-bisphosphate + chondroitin sulfate A 6'-sulfate
-
-
-
-
?
3'-phosphoadenylyl sulfate + chondroitin sulfate A
adenosine 3',5'-bisphosphate + chondroitin sulfate E
-
-
-
-
?
3'-phosphoadenylyl sulfate + dermatan sulfate
adenosine 3',5'-bisphosphate + dermatan sulfate 6'-sulfate
-
source pig skin
-
-
?
3'-phosphoadenylyl sulfate + GalNAc(4SO4)-D-glucuronic acid-GalNAc(4SO4)
adenosine 3',5'-bisphosphate + GalNAc(4,6SO4)-D-glucuronic acid-GalNAc(4SO4)
-
-
-
-
?
3'-phosphoadenylyl sulfate + GalNAc(4SO4)-D-glucuronic acid-GalNAc(6SO4)
adenosine 3',5'-bisphosphate + GalNAc(4,6SO4)-D-glucuronic acid-GalNAc(6SO4)
-
-
-
-
?
3'-phosphoadenylyl sulfate + GalNAc(4SO4)-Glc(2SO4)-GalNAc(6SO4)
adenosine 3',5'-bisphosphate + GalNAc(4,6SO4)-Glc(2SO4)-GalNAc(6SO4)
-
acceptor is a derivative of chondroitin sulfate A
-
-
?
3'-phosphoadenylyl sulfate + glucuronic acid-GalNAc(SO4)-glucuronic acid-GalNAc(SO4)
adenosine 3',5'-bisphosphate + ?
-
-
-
-
?
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
-
-
-
-
?
3'-phosphoadenylyl sulfate + UDP-GalNAc 4-sulfate
adenosine 3',5'-bisphosphate + UDP-GalNAc-4,6-disulfate
-
-
-
-
?
3'-phosphoadenylyl sulfate + chondroitin
adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate
-
-
-
?
3'-phosphoadenylyl sulfate + chondroitin
adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate
2.5% of activity compared with 4-sulfated pentasaccharide
-
-
?
3'-phosphoadenylyl sulfate + chondroitin
adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate
synthesis of chondroitin sulfate E
-
-
?
3'-phosphoadenylyl sulfate + chondroitin
adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate
involved in biosynthesis of chondroitin sulfate E, is one of the final steps in the chondroitin sulfate pathway creating disulfated GalNAc residues
-
-
?
3'-phosphoadenylyl sulfate + chondroitin
adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate
-
-
-
-
?
3'-phosphoadenylyl sulfate + chondroitin
adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate
-
a sulfotransferase that modifies galactosyl containing peptides to form chondroitin sulfates
-
-
?
additional information
?
-
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
-
-
?
additional information
?
-
-
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
-
-
?
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 sulfate + chondroitin
adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate
3'-phosphoadenylyl sulfate + chondroitin
adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate
-
-
-
-
?
3'-phosphoadenylyl sulfate + chondroitin sulfate A
adenosine 3',5'-bisphosphate + chondroitin sulfate E
-
-
-
-
?
3'-phosphoadenylyl sulfate + chondroitin
adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate
synthesis of chondroitin sulfate E
-
-
?
3'-phosphoadenylyl sulfate + chondroitin
adenosine 3',5'-bisphosphate + chondroitin 6'-sulfate
involved in biosynthesis of chondroitin sulfate E, is one of the final steps in the chondroitin sulfate pathway creating disulfated GalNAc residues
-
-
?
additional information
?
-
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
-
-
?
additional information
?
-
-
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
-
-
?
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(1R,3R,4S)-menthyl 2-acetamido-2-deoxy-4-O-sulfonato-beta-D-galactopyranoside
-
-
(1S,3S,4R)-menthyl 2-acetamido-2-deoxy-4-O-sulfonato-beta-D-galactopyranoside
-
weak inhibition
17beta-hydroxyestra-1,3,5(10)-trien-3-yl 2-acetamido-2-deoxy-4-O-sulfonato-beta-D-galactopyranoside
-
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
-
-
phenyl 2-acetamido-2-deoxy-beta-D-galactopyranoside 4-O-sulfate
-
competitive, 5 mM, 24% residual activity
additional information
-
not inhibited by cyclohexyl 2-acetamido-2,6-dideoxy-4-O-sulfonato-beta-D-galactopyranoside
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
CaCl2
-
5 mM, 2.5 fold stimulation of interior sulfotransferase activity, 1.9 fold stimulation of terminal sulfotransferase activity
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
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 37°C
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
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 37°C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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
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
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
the enzyme is principally Golgi associated, a small portion of the enzyme is located at the cell surface
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). CHSTF_HUMAN
561
1
64926
Swiss-Prot
other Location (Reliability: 2)
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
medicine
tumor-specific chondroitin sulfate modifications might be potential targets to influence tumor development
medicine
-
mRNA expressed by astrocytic tumor cells is associated with poor patient prognosis in case of astrocytic tumor, likely by enhancing chondroitin sulfate-E-unit-mediated tumor cell motility in the presence of pleiotrophin and/or midkine
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Sawada, T.; Fujii, S.; Nakano, H.; Ohtake, S.; Kimata, K.; Habuchi, O.
Synthesis of sulfated phenyl 2-acetamido-2-deoxy-D-galactopyranosides. 4-O-Sulfated phenyl 2-acetamido-2-deoxy-beta-D-galactopyranoside is a competitive acceptor that decreases sulfation of chondroitin sulfate by N-acetylgalactosamine 4-sulfate 6-O-sulfotransferase
Carbohydr. Res.
340
1983-1996
2005
Homo sapiens
Inoue, H.; Otsu, K.; Suzuki, S.; Nakanishi, Y.
Difference between N-acetylgalactosamine 4-sulfate 6-O-sulfotransferases from human serum and squid cartilage in specificity toward the terminal and interior portion of chondroitin sulfate
J. Biol. Chem.
261
4470-4475
1986
Homo sapiens
Ohtake, S.; Ito, Y.; Fukuta, M.; Habuchi, O.
Human N-acetylgalactosamine 4-sulfate 6-O-sulfotransferase cDNA is related to human B cell recombination activating gene-associated gene
J. Biol. Chem.
276
43894-43900
2001
Homo sapiens (Q7LFX5), Homo sapiens
Ohtake, S.; Kimata, K.; Habuchi, O.
A unique nonreducing terminal modification of chondroitin sulfate by N-acetylgalactosamine 4-sulfate 6-o-sulfotransferase
J. Biol. Chem.
278
38443-38452
2003
Homo sapiens
Ito, Y.; Watanabe, M.; Nishizawa, T.; Omachi, T.; Kobayashi, T.; Kasama, S.; Habuchi, O.; Nakayama, J.
The utility of formalin-fixed and paraffin-embedded tissue blocks for quantitative analysis of N-acetylgalactosamine 4-sulfate 6-O-sulfotransferase mRNA expressed by colorectal cancer cells
Acta Histochem. Cytochem.
40
53-59
2007
Homo sapiens (Q7LFX5), Homo sapiens
ten Dam, G.B.; van de Westerlo, E.M.; Purushothaman, A.; Stan, R.V.; Bulten, J.; Sweep, F.C.; Massuger, L.F.; Sugahara, K.; van Kuppevelt, T.H.
Antibody GD3G7 selected against embryonic glycosaminoglycans defines chondroitin sulfate-E domains highly up-regulated in ovarian cancer and involved in vascular endothelial growth factor binding
Am. J. Pathol.
171
1324-1333
2007
Homo sapiens (Q7LFX5)
Pai, T.; Chen, Q.; Zhang, Y.; Zolfaghari, R.; Ross, A.C.
Galactomutarotase and other galactose-related genes are rapidly induced by retinoic acid in human myeloid cells
Biochemistry
46
15198-15207
2007
Homo sapiens
Nozaki, H.; Tomoyama, Y.; Takagi, H.; Yokoyama, K.; Yamada, C.; Kaio, K.; Tsukimori, M.; Nagao, K.; Itakura, Y.; Ohtake-Niimi, S.; Nakano, H.; Habuchi, O.
Inhibition of N-acetylgalactosamine 4-sulfate 6-O-sulfotransferase by -D-4-O-sulfo-N-acetylgalactosaminides bearing various hydrophobic aglycons
Glycoconj. J.
27
237-248
2010
Homo sapiens
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