5.1.3.17: heparosan-N-sulfate-glucuronate 5-epimerase
This is an abbreviated version!
For detailed information about heparosan-N-sulfate-glucuronate 5-epimerase, go to the full flat file.
Word Map on EC 5.1.3.17
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5.1.3.17
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l-iduronic
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d-glucuronic
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epimerization
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proteoglycans
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idoa
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glycosaminoglycans
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glca
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n-sulfated
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2-o-sulfotransferase
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hexuronic
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hspgs
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2-o-sulfation
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mastocytoma
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mannuronan
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lindahl
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o-desulfated
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medicine
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diagnostics
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analysis
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synthesis
- 5.1.3.17
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l-iduronic
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d-glucuronic
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epimerization
- proteoglycans
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idoa
- glycosaminoglycans
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glca
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n-sulfated
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2-o-sulfotransferase
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hexuronic
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hspgs
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2-o-sulfation
- mastocytoma
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mannuronan
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lindahl
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o-desulfated
- medicine
- diagnostics
- analysis
- synthesis
Reaction
Synonyms
C5 uronosyl epimerase, C5-epi, C5-epimerase, D-Glucuronyl C-5 epimerase, D-glucuronyl C5-epimerase, Epimerase, polyglucuronate, Glce, GlceA, GlceB, glucuronosyl C-5 epimerase, glucuronyl C5-epimerase, heparan sulfate C-5 epimerase, Heparan sulfate C5-epimerase, Heparosan N-sulfate D-glucuronosyl 5-epimerase, heparosan-glucuronate 5-epimerase, Heparosan-N-sulfate-D-glucuronosyl-5-epimerase, HG-5epi, HNSG-5epi, HS C5-epimerase, HS glucuronyl C5-epimerase, Hsepi, RED-C5-epimerase
ECTree
5.1.3.17 heparosan-N-sulfate-glucuronate 5-epimeraseAdvanced search results
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results (Substrates Products
Substrates Products on EC 5.1.3.17 - heparosan-N-sulfate-glucuronate 5-epimerase
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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
GlcA-beta-(1->4)-GlcNAc-beta-(1->4)-GlcA-beta-(1->4)-GlcNS-beta-(1->4)-GlcA-beta-(1->4)-GlcNAc-beta-(1->4)-GlcA-beta-(1->4)-2,5-andydro-D-mannitol
GlcA-beta-(1->4)-GlcNAc-beta-(1->4)-GlcA-beta-(1->4)-GlcNS-beta-(1->4)-IdoA-beta-(1->4)-GlcNAc-beta-(1->4)-GlcA-beta-(1->4)-2,5-andydro-D-mannitol
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i.e. Octa-4
i.e. epi-Octa-4
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ir
GlcA-beta-(1->4)-GlcNAc-beta-(1->4)-GlcA-beta-(1->4)-GlcNS-beta-(1->4)-GlcA-beta-(1->4)-GlcNS-beta-(1->4)-GlcA-beta-(1->4)-2,5-andydro-D-mannitol
GlcA-beta-(1->4)-GlcNAc-beta-(1->4)-GlcA-beta-(1->4)-GlcNS-beta-(1->4)-GlcA-beta-(1->4)-GlcNS-beta-(1->4)-GlcA-beta-(1->4)-2,5-andydro-D-mannitol
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i.e. Octa-3, two GlcA units in Octa-1 are susceptible to C5-epi modification, and both epimerization sites are reversible
i.e. epi-Octa-3
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ir
GlcA-beta-(1->4)-GlcNAc-beta-(1->4)-GlcA-beta-(1->4)-GlcNS-beta-(1->4)-GlcA-beta-(1->4)-GlcNS-beta-(1->4)-GlcA-beta-(1->4)-GlcNS-beta-(1->4)-GlcA-beta-(1->4)-2,5-andydro-D-mannitol
GlcA-beta-(1->4)-GlcNAc-beta-(1->4)-GlcA-beta-(1->4)-GlcNS-beta-(1->4)-IdoA-beta-(1->4)-GlcNS-beta-(1->4)-IdoA-beta-(1->4)-GlcNS-beta-(1->4)-GlcA-beta-(1->4)-2,5-andydro-D-mannitol
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i.e. Deca-8 with GlcA-beta-(1->4)-GlcNAc-beta-(1->4)-GlcA-beta-(1->4)-GlcNS-beta-(1->4)-GlcA(irreversible site)-beta-(1->4)-GlcNS-beta-(1->4)-GlcA (reversible site)-beta-(1->4)-GlcNS-beta-(1->4)-GlcA-beta-(1->4)-2,5-andydro-D-mannitol
i.e. epi-Deca-8
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?
GlcA-beta-(1->4)-GlcNH2-beta-(1->4)-GlcA-beta-(1->4)-GlcNS-beta-(1->4)-GlcA-beta-(1->4)-GlcNS-beta-(1->4)-GlcA-beta-(1->4)-2,5-andydro-D-mannitol
GlcA-beta-(1->4)-GlcNH2-beta-(1->4)-GlcA-beta-(1->4)-GlcNS-beta-(1->4)-IdoA-beta-(1->4)-GlcNS-beta-(1->4)-GlcA-beta-(1->4)-2,5-andydro-D-mannitol
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i.e. Octa-6
i.e. epi-Octa-6
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r
GlcA-beta-(1->4)-GlcNS-beta-(1->4)-GlcA-beta-(1->4)-GlcNS-beta-(1->4)-GlcA-beta-(1->4)-2,5-andydro-D-mannitol
GlcA-beta-(1->4)-GlcNS-beta-(1->4)-IdoA-beta-(1->4)-GlcNS-beta-(1->4)-GlcA-beta-(1->4)-2,5-andydro-D-mannitol
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i.e. Hexa-7
i.e. epi-Hexa-7
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r
GlcA-beta-(1->4)-GlcNS-beta-(1->4)-GlcA-beta-(1->4)-GlcNS-beta-(1->4)-GlcA-beta-(1->4)-GlcNAc-beta-(1->4)-GlcA-beta-(1->4)-2,5-andydro-D-mannitol
GlcA-beta-(1->4)-beta-(1->4)-GlcNS-beta-(1->4)-L-IdoA-alpha-(1->4)-GlcNS-beta-(1->4)-L-IdoA-alpha-(1->4)-GlcNAc-beta-(1->4)-GlcA-beta-(1->4)-2,5-andydro-D-mannitol
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i.e. Octa-1, two GlcA units in Octa-1 are susceptible to C5-epi modification, and both epimerization sites are reversible
i.e. epi-Octa-1
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r
GlcA-beta-(1->4)-GlcNS-beta-(1->4)-GlcA-beta-(1->4)-GlcNS-beta-(1->4)-GlcA-beta-(1->4)-GlcNS-beta-(1->4)-GlcA-beta-(1->4)-2,5-andydro-D-mannitol
GlcA-beta-(1->4)-GlcNS-beta-(1->4)-IdoA-beta-(1->4)-GlcNS-beta-(1->4)-IdoA-beta-(1->4)-GlcNS-beta-(1->4)-GlcA-beta-(1->4)-2,5-andydro-D-mannitol
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i.e. Octa-2
i.e. epi-Octa-2
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r
Heparosan-N-sulfate D-glucuronate
Heparosan-N-sulfate L-iduronate
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-
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?
Heparosan-N-sulfate D-glucuronate
Heparosan-N-sulfate L-iduronate
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heparosan N-sulfate prepared by metabolic labeling of a capsular polysaccharide from E. coli K5 and subsequent chemical partial N-deacetylation and N-sulfation. Approximately 30% of the D-glucuronyl residues located between two N-sulfated glucosamine units are converted to L-iduronyl units
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?
Heparosan-N-sulfate D-glucuronate
Heparosan-N-sulfate L-iduronate
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-
-
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?
Heparosan-N-sulfate D-glucuronate
Heparosan-N-sulfate L-iduronate
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-
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?
Heparosan-N-sulfate D-glucuronate
Heparosan-N-sulfate L-iduronate
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C5-epimerization is irreversible in vivo
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-
ir
Heparosan-N-sulfate D-glucuronate
Heparosan-N-sulfate L-iduronate
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development of a coupled assay method using the enzyme and a 2-O-sulfotransferase mutant 2OST Y94I, overview
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?
Heparosan-N-sulfate D-glucuronate
Heparosan-N-sulfate L-iduronate
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-
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?
Heparosan-N-sulfate D-glucuronate
Heparosan-N-sulfate L-iduronate
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a D-glucuronosyl residue is recognized as a substrate if it is linked at C-1 to an N-acetyl glucosamine residue and at C-4 to a N-sulfated unit. Large substrates are preferred
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?
Heparosan-N-sulfate D-glucuronate
Heparosan-N-sulfate L-iduronate
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the enzyme controle heparan sulfate chain flexibility, its activity, modifiying the substrate, is required for proper lymphoid organ development, overview
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?
Heparosan-N-sulfate D-glucuronate
Heparosan-N-sulfate L-iduronate
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-
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?
Heparosan-N-sulfate D-glucuronate
Heparosan-N-sulfate L-iduronate
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the enzyme controle heparan sulfate chain flexibility, its activity, modifiying the substrate, is required for proper lymphoid organ development, overview
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?
additional information
?
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enzyme catalyzes formation of L-iduronic acid residues in the course of heparin biosynthesis
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?
additional information
?
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enzyme is involved in the biosynthesis of heparan sulfate in liver
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?
additional information
?
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key heparan sulfate modifying enzyme, a biosynthetic step that enhances biological activity of heparan sulfate. The enzyme is an important determinant of dorso-ventral axis formation and patterning in zebrafish
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?
additional information
?
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heparin hexasaccharide is product of Glce following O-sulfation, structure of the Glce dimer in complex with heparin hexasaccharide, detailed overview
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?
additional information
?
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limiting factor in dermatan sulfate biosynthesis
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?
additional information
?
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the D-glucuronyl C5-epimerase gene is transcriptionally activated through the beta-catenin-TCF4 pathway
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?
additional information
?
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the D-glucuronyl C5-epimerase gene is transcriptionally activated through the beta-catenin-TCF4 pathway
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?
additional information
?
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the enzyme is known for being a two-way catalytic enzyme, displaying a reversible catalytic mode by converting a glucuronic acid to an iduronic acid residue, and vice versa. The enzyme can also serve as a one-way catalyst to convert a glucuronic acid to an iduronic acid residue, displaying an irreversible catalytic mode. The reversible or irreversible catalytic mode strictly depends on the saccharide substrate structures
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?
additional information
?
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oligosaccharides containing a nonreducing end GlcNS residue immediately adjacent to the EPS residue are reactive to the enzyme. In contrast, when the GlcNS is replaced with GlcNAc, the oligosaccharide is no longer a substrate of the enzyme, substrate specificity, overview. No activity with GlcA-beta-(1->4)-GlcNAc-beta-(1->4)-GlcA-beta-(1->4)-GlcNAc-beta-(1->4)-GlcA-beta-(1->4)-GlcNAc-beta-(1->4)-GlcA-beta-(1->4)-2,5-andydro-D-mannitol. Determination of epimerization sites in different substrates and reaction reversibility using D2O and tandem mass spectrometry, critical role of N-sulfated glucosamine at the nonreducing end of the epimerization site
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?
additional information
?
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development and evaluation of a rapid, nonradioactive assay for measuring heparan sulfate C-5 epimerase activity using hydrogen/deuterium exchange-mass spectrometry, overview. The method involves the following steps: H/D exchange upon epimerization of the substrate with HS C5-epimerase, low-pH nitrous acid treatment of the substrate, the separation of low-pH nitrous acid-cleaved disaccharides using HPLC, and mass spectrometry analysis
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?
additional information
?
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development and evaluation of a rapid, nonradioactive assay for measuring heparan sulfate C-5 epimerase activity using hydrogen/deuterium exchange-mass spectrometry, overview. The method involves the following steps: H/D exchange upon epimerization of the substrate with HS C5-epimerase, low-pH nitrous acid treatment of the substrate, the separation of low-pH nitrous acid-cleaved disaccharides using HPLC, and mass spectrometry analysis
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?
additional information
?
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recombinant enzyme HG-5epi, expressed in insect cells, epimerizes GlcA residues in heparosan, but not in N-sulfated-heparosan. Conversion of IdoA to GlcA is also catalyzed by HG-5epi when completely desulfated N-acetylated heparin is used as the substrate, indicating a reversible reaction mechanism. At equilibrium of the epimerization, the proportion of IdoA in the reaction product reaches up to 30% of total hexuronic acid. The recombinant enzyme catalyzes the epimerization of non-sulfated heparosan, product identification by using a combination of anion-exchange HPLC and postcolumn fluorescent labeling system
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?
additional information
?
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recombinant enzyme HG-5epi, expressed in insect cells, epimerizes GlcA residues in heparosan, but not in N-sulfated-heparosan. Conversion of IdoA to GlcA is also catalyzed by HG-5epi when completely desulfated N-acetylated heparin is used as the substrate, indicating a reversible reaction mechanism. At equilibrium of the epimerization, the proportion of IdoA in the reaction product reaches up to 30% of total hexuronic acid. The recombinant enzyme catalyzes the epimerization of non-sulfated heparosan, product identification by using a combination of anion-exchange HPLC and postcolumn fluorescent labeling system
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?
additional information
?
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enzyme catalyzes formation of L-iduronic acid residues in the course of heparin biosynthesis
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?
additional information
?
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L-iduronosyl moieties are formed after N-sulfation but before O-sulfation
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?
additional information
?
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the enzyme is involved in the biosynthesis of heparin and heparan sulfate
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?
additional information
?
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the enzyme is involved in the biosynthesis of heparin and heparan sulfate
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?
additional information
?
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analysis of N-sulfation and glycosylation patterns, as well as chain lengths of heparan sulfate samples from wild-type and mutant cells, overview
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?
