Information on EC 2.8.2.30 - [heparan sulfate]-glucosamine 3-sulfotransferase 3

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.8.2.30
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RECOMMENDED NAME
GeneOntology No.
[heparan sulfate]-glucosamine 3-sulfotransferase 3
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
3'-phosphoadenylyl sulfate + [heparan sulfate]-glucosamine = adenosine 3',5'-bisphosphate + [heparan sulfate]-glucosamine 3-sulfate
show the reaction diagram
Two major substrates contain the tetrasaccharides: undetermined 2-sulfo-uronic acid-GlcN2S-IdoA2S-GlcN*- and undetermined 2-sulfo-uronic acid-GlcN2S-IdoA2S-GlcN6S with modification of the N-unsubstituted glucosamine residue. Modification of selected sequences containing N-sulfo-glucosamine residues cannot yet be excluded. The 3-O-sulfated heparan sulfate can be utilized by Herpes simplex virus type 1 as an entry receptor to infect the target cells. There are two isoenzymes, known as 3-OST-3A and 3-OST-3B, which have identical catalytic domains but are encoded by different mammalian genes. The specificity of this enzyme differs from that of other [heparan sulfate]-glucosamine 3-sulfotransferases. It is inefficient at modifying precursors of antithrombin binding site, in contrast to EC 2.8.2.23, [heparan sulfate]-glucosamine 3-sulfotransferase 1, and it does not modify glucosamine preceded by GlcA2S, unlike EC 2.8.2.29, [heparan sulfate]-glucosamine 3-sulfotransferase 2
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
sulfate group transfer
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
heparan sulfate biosynthesis (late stages)
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Glycosaminoglycan biosynthesis - heparan sulfate / heparin
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SYSTEMATIC NAME
IUBMB Comments
3'-phosphoadenylyl-sulfate:[heparan sulfate]-glucosamine 3-sulfotransferase
Two major substrates contain the tetrasaccharides: -> undetermined 2-sulfo-uronic acid-> GlcN2S-> IdoA2S-> GlcN*-> and -> undetermined 2-sulfo-uronic acid-> GlcN2S-> IdoA2S-> GlcN6S*-> (symbols as in 2-Carb-38) with modification of the N-unsubstituted glucosamine residue (shown with an asterisk) [1,4]. Modification of selected sequences containing N-sulfo-glucosamine residues cannot yet be excluded. The 3-O-sulfated heparan sulfate can be utilized by Herpes simplex virus type 1 as an entry receptor to infect the target cells [2]. There are two isozymes, known as 3-OST-3A and 3-OST-3B, which have identical catalytic domains but are encoded by different mammalian genes [3]. The specificity of this enzyme differs from that of the other [heparan sulfate]-glucosamine 3-sulfotransferases. It is inefficient at modifying precursors of the antithrombin binding site [in contrast to EC 2.8.2.23 ([heparan sulfate]-glucosamine 3-sulfotransferase 1)] and it does not modify glucosamine preceded by GlcA2S [unlike EC 2.8.2.29 ([heparan sulfate]-glucosamine 3-sulfotransferase 2)].
CAS REGISTRY NUMBER
COMMENTARY hide
183257-54-7
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
HSV-1
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Manually annotated by BRENDA team
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M0RAN2
UniProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
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knocking down enzyme receptor in fibroblasts cells significantly reduces HSV-1 entry and glycoprotein D binding to cells
physiological function
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 sulfate
?
show the reaction diagram
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chondroitin sulfate exhibits similar high affinity binding to 3-OST-3A compared to heparan sulfate
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?
3'-phosphoadenylyl sulfate + chondroitin sulfate A
adenosine 3',5'-diphosphate + ?
show the reaction diagram
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isoform 3A, low activity
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?
3'-phosphoadenylyl sulfate + GlcA-beta-(1->4)-GlcNS6S-beta-(1->4)-IdoA-beta-(1->4)-GlcNS6S-alpha-(CH2)5NH2
adenosine 3',5'-bisphosphate + GlcA-beta-(1->4)-GlcNS3S6S-beta-(1->4)-IdoA-beta-(1->4)-GlcNS6S-alpha-(CH2)5NH2
show the reaction diagram
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?
3'-phosphoadenylyl sulfate + GlcA-beta-(1->4)-GlcNS6S-beta-(1->4)-IdoA-beta-(1->4)-GlcNS6S-beta-(1->4)-GlcA-beta-(1->4)-GlcNS6S-alpha-(CH2)5NH2
adenosine 3',5'-bisphosphate + GlcA-beta-(1->4)-GlcNS3S6S-beta-(1->4)-IdoA-beta-(1->4)-GlcNS3S6S-beta-(1->4)-GlcA-beta-(1->4)-GlcNS6S-alpha-(CH2)5NH2
show the reaction diagram
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?
3'-phosphoadenylyl sulfate + heparin
?
show the reaction diagram
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heparin exhibits similar high affinity binding to 3-OST-3A compared to heparan sulfate
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?
3'-phosphoadenylyl sulfate + IdoA-beta-(1->4)-GlcNS6S-beta-(1->4)-IdoA-beta-(1->4)-GlcNS6S-alpha-(CH2)5NH2
adenosine 3',5'-bisphosphate + IdoA-beta-(1->4)-GlcNS3S6S-beta-(1->4)-IdoA-beta-(1->4)-GlcNS6S-alpha-(CH2)5NH2
show the reaction diagram
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?
3'-phosphoadenylyl sulfate + keratan sulfate
adenosine 3',5'-diphosphate + ?
show the reaction diagram
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isoform 3A, low activity
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?
3'-phosphoadenylyl sulfate + [heparan sulfate]-glucosamine
adenosine 3',5'-bisphosphate + [heparan sulfate]-glucosamine 3-sulfate
show the reaction diagram
3'-phosphoadenylyl sulfate + [heparan sulfate]-glucosamine
adenosine 3',5'-diphosphate + [heparan sulfate]-glucosamine 3-sulfate
show the reaction diagram
heparan sulfate + 3'-phosphoadenylyl sulfate
3-O-sulfated heparan sulfate + adenosine 3',5'-bisphosphate
show the reaction diagram
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i.e. PAPS
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?
heparin 3-hydroxy octasaccharide + 3'-phosphoadenylyl sulfate
3-O-sulfated heparin octasaccharide + adenosine 3',5'-bisphosphate
show the reaction diagram
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 + [heparan sulfate]-glucosamine
adenosine 3',5'-bisphosphate + [heparan sulfate]-glucosamine 3-sulfate
show the reaction diagram
3'-phosphoadenylyl sulfate + [heparan sulfate]-glucosamine
adenosine 3',5'-diphosphate + [heparan sulfate]-glucosamine 3-sulfate
show the reaction diagram
heparan sulfate + 3'-phosphoadenylyl sulfate
3-O-sulfated heparan sulfate + adenosine 3',5'-bisphosphate
show the reaction diagram
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i.e. PAPS
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?
additional information
?
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Na+
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the enzyme contains sodium
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
5-aza-2'-deoxycytidine
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exposure of chondrosarcoma cells to the DNA-methyltransferase inhibitor 5-Aza-dc up-regulates expression of 3-OST3A mRNA
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
additional information
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cyclosporine B heparin binding kinetics, overview
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
22
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assay at room temperature
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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H-EMC-SS chondrosarcoma cell
Manually annotated by BRENDA team
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3-OST-3 expression analysis
Manually annotated by BRENDA team
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primary corneal, 3-OST-3 expression analysis
Manually annotated by BRENDA team
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clone E6-1,expresssion of 3-OST-3B isoform
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
M0RAN2
from bone marrow
Manually annotated by BRENDA team
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of peripheral blood, expresssion of 3-OST-3B isoform
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
33000
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x * 33743, His6-tagged truncated mutant, amino acid sequence calculation, x * 33000, recombinant His6-tagged truncated mutant, SDS-PAGE
33743
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x * 33743, His6-tagged truncated mutant, amino acid sequence calculation, x * 33000, recombinant His6-tagged truncated mutant, SDS-PAGE
39000
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x * 39000, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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analysis of the overall structural integrity of recombinant 3-OST-3A by steady-state fluorescence spectroscopy, secondary structure with a content of 38.7% alpha-helix and 13.3% beta-sheet, overview
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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thermal unfolding kinetics of the purified recombinant His6-tagged truncated mutant protein, overview
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Co2+ affinity chromatography and heparin-agarose column chromatography; recombinant N-terminally His6-tagged truncated mutant isozyme 3-OST-3A lacking the cytoplasmic, transmembrane and SPLAG domain from Escherichia coli by cobalt and heparin affinity chromatography, followed by dialysis, to over 95% puritiy
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recombinant N-terminally His6-tagged 3-OST-3 catalytic domain, comprising residues Gly139-Gly406, from Escherichia coli
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to homogeneity, recombinant isoform 3A
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Toyopearl AF-heparin 650M column chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
3-OST-3, transient expression in CHO-K1 cells
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3-OST3A cDNA is inserted into the expression vector pCDNA3.1 for transfection of HEMC cells
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DNA and amino acid sequence determination and analysis and developmental expression analysis of the 3-OST gene family, sequence comparisons, phylogentic analysis, overview
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expressed in CHO-K1 cells
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expressed in Escherichia coli strain BL21(DE3)pLysS; expression of the N-terminally His6-tagged truncated mutant isozyme 3-OST-3A lacking the cytoplasmic, transmembrane and SPLAG domain
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expressed in Sf9 insect cells
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expression in CHO cells
expression in COS-7 cells
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expression in Sf9 cells
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expression of N-terminally His6-tagged 3-OST-3 catalytic domain, comprising residues Gly139-Gly406, in Escherichia coli
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
3-OST3A is epigenetically repressed in breast cancer cell lines (except SKBR-3 cells)
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exposure of chondrosarcoma cells to 5-aza-2'-deoxycytidine up-regulates expression of 3-OST3A mRNA
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following treatment with 5-aza-2'-deoxycytidine at 24 h and both 5-aza-2'-deoxycytidine in combination with trichostatin-A at 48 h, isoform 3-OST-3B1 gene expression is activated in the pancreatic cancer cell line PANC-1
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mRNA and protein levels are upregulated in calcified cell spheroids of bone marrow mesenchymal stromal cells
M0RAN2
mRNA expression of isoform HS3ST3A1 is decreased by 27% in placental tissue obtained from preeclamptic compared to normotensive women
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the enzyme is down-regulated 10fold in the hepatocytes of chronic hepatitis B virus infection model
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the expression of isoform HS3ST3B is markedly up-regulated in human primary monocytes and the related cell line THP-1 after exposure to toll-like receptor agonists. tumor necrosis factor-alpha is also efficient, to a lesser extent, to increase isoform HS3ST3B expression, while interleukin-6, interleukin-4, and interferon-gamma are poor inducers. Lipopolysaccharide induces a rapid and strong transcription of the HS3ST3B1 gene
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
K259A
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the mutant shows 13.1% activity compared to the wild type enzyme
T256A
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the mutant shows 101.5% activity compared to the wild type enzyme
T256E
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the mutant shows 13.1% activity compared to the wild type enzyme
T256V
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the mutant shows 59.4% activity compared to the wild type enzyme
W283A
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the mutant shows 7.6% activity compared to the wild type enzyme
additional information
Renatured/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
addition of 6 M guanidinium-HCl results in a red shift of the emission maximum by 12 nm indicating that the enzyme is properly folded after purification
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
drug development
medicine