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Information on EC 2.4.1.175 - glucuronosyl-N-acetylgalactosaminyl-proteoglycan 4-beta-N-acetylgalactosaminyltransferase and Organism(s) Escherichia coli and UniProt Accession Q8L0V4
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2.4.1.175 glucuronosyl-N-acetylgalactosaminyl-proteoglycan 4-beta-N-acetylgalactosaminyltransferaseIUBMB Comments
Involved in the biosynthesis of chondroitin sulfate. The human form of this enzyme is a bifunctional glycosyltransferase, which also has the 3-beta-glucuronosyltransferase (EC 2.4.1.226, N-acetylgalactosaminyl-proteoglycan 3-beta-glucuronosyltransferase) activity required for the synthesis of the chondroitin sulfate disaccharide repeats. Similar chondroitin synthase 'co-polymerases' can be found in Pasteurella multocida and Escherichia coli.
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Word Map
- 2.4.1.175
- glycosaminoglycans
- n-acetylgalactosamine
- udp-galnac
-
glcua
-
sulfotransferases
- medicine
-
glucuronyltransferase
- hexasaccharide
- udp-glca
- udp-sugars
-
d-glucuronic
-
chemo-enzymatically
- diagnostics
The taxonomic range for the selected organisms is: Escherichia coli
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota, Archaea
Reaction Schemes
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[protein]-3-O-(beta-D-GlcA-(1->3)-beta-D-GalNAc-(1->4)-beta-D-GlcA-(1->3)-beta-D-Gal-(1->3)-beta-D-Gal-(1->4)-beta-D-Xyl)-L-serine
=
+
[protein]-3-O-(beta-D-GalNAc-(1->4)-beta-D-GlcA-(1->3)-beta-D-GalNAc-(1->4)-beta-D-GlcA-(1->3)-beta-D-Gal-(1->3)-beta-D-Gal-(1->4)-beta-D-Xyl)-L-serine
+
=
+
+
[protein]-3-O-(beta-D-GlcA-(1->3)-[beta-D-GalNAc-(1->4)-beta-D-GlcA-(1->3)]n-beta-D-GalNAc-(1->4)-beta-D-GlcA-(1->3)-beta-D-Gal-(1->3)-beta-D-Gal-(1->4)-beta-D-Xyl)-L-serine
=
+
[protein]-3-O-([beta-D-GalNAc-(1->4)-beta-D-GlcA-(1->3)]n+1-beta-D-GalNAc-(1->4)-beta-D-GlcA-(1->3)-beta-D-Gal-(1->3)-beta-D-Gal-(1->4)-beta-D-Xyl)-L-serine
Synonyms
chondroitin polymerase, chsy-2, chondroitin synthase-1, csgalnact-2, n-acetylgalactosaminyltransferase ii, chondroitin synthase 1, cs synthase-1, cs glycosyltransferase, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
acetylgalactosaminyltransferase, uridine diphosphoacetylgalactosamine-chondroitin, II
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chondroitin synthase
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glucuronyl-N-acetylgalactosaminylproteoglycan beta1,4-N-acetylgalactosaminyltransferase
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-
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N-acetylgalactosaminyltransferase II
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UDP-N-acetyl-D-galactosamine:D-glucuronyl-N-acetyl-1,3-beta-D-galactosaminylproteoglycan beta-1,4-N-acetylgalactosaminyltransferase
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uridine diphosphoacetylgalactosamine-chondroitin acetylgalactosaminyltransferasec II
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additional information
additional information
the enzyme also has the 3-beta-glucuronosyltransferase, EC 2.4.1.226, activity
additional information
the human form of this enzyme is a bifunctional glycosyltransferase, which also has the 3-beta-glucuronosyltransferase, EC 2.4.1.226, activity required for the synthesis of the chondroitin sulfate disaccharide repeats. Similar chondroitin synthase co-polymerases can be found in Pasteurella multocida and Escherichia coli.
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hexosyl group transfer
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
UDP-N-acetyl-D-galactosamine:beta-D-glucuronosyl-(1->3)-N-acetyl-beta-D-galactosaminyl-proteoglycan 4-beta-N-acetylgalactosaminyltransferase
Involved in the biosynthesis of chondroitin sulfate. The human form of this enzyme is a bifunctional glycosyltransferase, which also has the 3-beta-glucuronosyltransferase (EC 2.4.1.226, N-acetylgalactosaminyl-proteoglycan 3-beta-glucuronosyltransferase) activity required for the synthesis of the chondroitin sulfate disaccharide repeats. Similar chondroitin synthase 'co-polymerases' can be found in Pasteurella multocida and Escherichia coli.
CAS REGISTRY NUMBER
COMMENTARY
96189-40-1
-
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
UDP-N-acetyl-alpha-D-galactosamine + (glucuronyl-N-acetyl-1,3-beta-D-galactosamine)2
UDP + N-acetyl-beta-D-galactosaminyl-1,4-glucuronyl-N-acetyl-1,3-beta-D-galactosaminyl-glucuronyl-N-acetyl-1,3-beta-D-galactosamine
minimal required acceptor substrate chain length
-
-
?
UDP-N-acetyl-alpha-D-galactosamine + (glucuronyl-N-acetyl-1,3-beta-D-galactosamine)3
UDP + N-acetyl-beta-D-galactosaminyl-1,4-glucuronyl-N-acetyl-1,3-beta-D-galactosaminyl-(glucuronyl-N-acetyl-1,3-beta-D-galactosamine)2
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-
-
?
UDP-N-acetyl-alpha-D-galactosamine + chondroitin oligosaccharide
UDP + N-acetyl-beta-D-galactosaminyl chondroitin oligosaccharide
biosynthesis of K4 antigen, a capsule polysaccharide consisting of a chondroitin backbone to which beta-fructose is linked at position C-3 of the GlcNAc residue
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-
?
UDP-N-acetyl-alpha-D-galactosamine + chondroitin sulfate oligosaccharide
UDP + N-acetyl-beta-D-galactosaminyl chondroitin sulfate oligosaccharide
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-
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?
UDP-N-acetyl-beta-D-galactosamine + chondroitin sulfate hexasaccharide
?
-
-
-
?
UDP-N-acetyl-D-galactosamine + chondroitin oligosaccharide
UDP + N-acetyl-D-galactosaminyl chondroitin oligosaccharide
UDP-N-acetyl-D-galactosamine + chondroitin sulfate oligosaccharide
UDP + N-acetyl-D-galactosaminyl chondroitin sulfate oligosaccharide
acceptor substrates longer than a tetrasaccharide are absolutely required
-
?
UDP-alpha-D-glucuronate + N-acetyl-beta-D-galactosaminyl-[GlcA-GalNAc]n-pyridylamine
UDP + [GlcA-GalNAc]n+1-pyridylamine
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-
-
-
?
UDP-N-acetyl-alpha-D-galactosamine + chondroitin hexasaccharide
UDP + N-acetyl-beta-D-galactosaminyl chondroitin hexasaccharide
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-
-
-
?
UDP-N-acetyl-alpha-D-galactosamine + chondroitin oligosaccharide
UDP + N-acetyl-beta-D-galactosaminyl chondroitin oligosaccharide
-
biosynthesis of K4 antigen, a capsule polysaccharide consisting of a chondroitin backbone to which beta-fructose is linked at position C-3 of the GlcNAc residue
-
-
?
UDP-N-acetyl-alpha-D-galactosamine + chondroitin pentasaccharide
UDP + N-acetyl-beta-D-galactosaminyl chondroitin pentasaccharide
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-
-
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?
UDP-N-acetyl-alpha-D-galactosamine + chondroitin polysaccharide
UDP + N-acetyl-beta-D-galactosaminyl chondroitin polysaccharide
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-
-
-
?
UDP-N-acetyl-alpha-D-galactosamine + chondroitin sulfate oligosaccharide
UDP + N-acetyl-beta-D-galactosaminyl chondroitin sulfate oligosaccharide
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-
-
-
?
UDP-N-acetyl-alpha-D-galactosamine + [GlcA-GalNAc]n-pyridylamine
UDP + N-acetyl-beta-D-galactosaminyl-[GlcA-GalNAc]n-pyridylamine
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-
-
-
?
UDP-N-acetyl-alpha-D-glucosamine + chondroitin sulfate oligosaccharide
UDP + N-acetyl-beta-D-glucosaminyl chondroitin sulfate oligosaccharide
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weak activity
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-
?
UDP-N-acetyl-D-galactosamine + chondroitin oligosaccharide
UDP + N-acetyl-D-galactosaminyl chondroitin oligosaccharide
UDP-N-acetyl-D-galactosamine + chondroitin sulfate C
UDP + N-acetyl-D-galactosaminyl chondroitin sulfate C
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no activity
-
-
?
UDP-N-acetyl-D-galactosamine + chondroitin sulfate oligosaccharide
UDP + N-acetyl-D-galactosaminyl chondroitin sulfate oligosaccharide
-
no activity
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-
?
UDP-N-acetyl-D-galactosamine + defructosylated K4 oligosaccharide
UDP + N-acetyl-D-galactosaminyl defructosylated K4 oligosaccharide
UDP-N-acetyl-D-galactosamine + chondroitin oligosaccharide
UDP + N-acetyl-D-galactosaminyl chondroitin oligosaccharide
acceptors are even-numbered chondroitin oligosaccharides with terminal glucuronyl-N-acetyl-1,3-beta-D-galactosamine sequence at non-reducing end, transfers N-acetyl-galactosamine to non-reducing glucuronic acid residues in beta-glycosidic linkage
transfer in beta-1,4-linkage
?
UDP-N-acetyl-D-galactosamine + chondroitin oligosaccharide
UDP + N-acetyl-D-galactosaminyl chondroitin oligosaccharide
acceptor substrates longer than a tetrasaccharide are absolutely required
transfer in beta-1,4-linkage
?
UDP-N-acetyl-D-galactosamine + chondroitin oligosaccharide
UDP + N-acetyl-D-galactosaminyl chondroitin oligosaccharide
-
long polymers are not formed
-
?
UDP-N-acetyl-D-galactosamine + chondroitin oligosaccharide
UDP + N-acetyl-D-galactosaminyl chondroitin oligosaccharide
-
in vitro: addition of single sugars to a nonreducing terminal GlcNAc residue of a chondroitin-derived oligosaccharide acceptor
-
?
UDP-N-acetyl-D-galactosamine + defructosylated K4 oligosaccharide
UDP + N-acetyl-D-galactosaminyl defructosylated K4 oligosaccharide
-
the native K4 oligosaccharide, containing a fructose residue branch at C-3 of each GlcNAc residue of the chondroitin backbone, is no substrate
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?
UDP-N-acetyl-D-galactosamine + defructosylated K4 oligosaccharide
UDP + N-acetyl-D-galactosaminyl defructosylated K4 oligosaccharide
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in vitro: addition of single sugars to a nonreducing terminal GlcNAc residue of a chondroitin-derived oligosaccharide acceptor, but long polymers are not formed
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?
additional information
?
-
the enzyme also has the 3-beta-glucuronosyltransferase, EC 2.4.1.226, activity
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-
?
additional information
?
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the enzyme also has the 3-beta-glucuronosyltransferase, EC 2.4.1.226, activity
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-
?
additional information
?
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no hydrolysis activity is observed with UDP-N-glucuronic acid
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-
?
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
UDP-N-acetyl-alpha-D-galactosamine + chondroitin oligosaccharide
UDP + N-acetyl-beta-D-galactosaminyl chondroitin oligosaccharide
biosynthesis of K4 antigen, a capsule polysaccharide consisting of a chondroitin backbone to which beta-fructose is linked at position C-3 of the GlcNAc residue
-
-
?
UDP-N-acetyl-alpha-D-galactosamine + chondroitin sulfate oligosaccharide
UDP + N-acetyl-beta-D-galactosaminyl chondroitin sulfate oligosaccharide
-
-
-
?
UDP-N-acetyl-alpha-D-galactosamine + chondroitin oligosaccharide
UDP + N-acetyl-beta-D-galactosaminyl chondroitin oligosaccharide
-
biosynthesis of K4 antigen, a capsule polysaccharide consisting of a chondroitin backbone to which beta-fructose is linked at position C-3 of the GlcNAc residue
-
-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mn2+
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.005895
UDP-N-acetyl-alpha-D-glucosamine
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wild type enzyme, in 25 mM HEPES (pH 7.5), 100 mM NaCl, 20 mM MnCl2, 1 mM CaCl2, at 30°C
0.005895
UDP-N-acetyl-beta-D-galactosamine
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wild type enzyme, in 25 mM HEPES (pH 7.5), 100 mM NaCl, 20 mM MnCl2, 1 mM CaCl2, at 30°C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.00053
purified rcombinant enzyme, substrate chondroitin polysaccharide with MW 10 kDa
0.00124
purified rcombinant enzyme, substrate chondroitin hexasaccharide
0.00331
purified rcombinant enzyme, substrate chondroitin sulfate polysaccharide with MW 20 kDa
0.00334
purified rcombinant enzyme, substrate chondroitin sulfate hexasaccharide
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
additional information
-
transport of the nascent polymer chain out of the cell through the lipid membranes requires at least seven distinct polypeptide species, possible transport mechanism
-
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). PDB
SCOP
CATH
UNIPROT
ORGANISM
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
K4CP in the presence of UDP and UDP-N-acetylgalactosamine as well as with UDP and UDP-glucuronic acid, hanging drop vapor diffusion method and batch method, using 15-20% (w/v) PEG 3350 and 200 mM NaCl
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
glutathione Sepharose column chromatography and Superdex 200 gel filtration
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, expression as soluble His-tagged protein in Escherichia coli strain TOP10
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
medicine
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antimicrobial approach, understanding microbial capsule biosynthesis may assist the uncloaking of bacterial camouflage without disrupting host GAG synthesis
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Ninomiya, T.; Sugiura, N.; Tawada, A.; Sugimoto, K.; Watanabe, H.; Kimata, K.
Molecular cloning and characterization of chondroitin polymerase from Escherichia coli strain K4
J. Biol. Chem.
277
21567-21575
2002
Escherichia coli (Q8L0V4), Escherichia coli, Escherichia coli K4 (Q8L0V4)
DeAngelis, P.L.
Microbial glycosaminoglycan glycosyltransferases
Glycobiology
12
9R-16R
2002
Escherichia coli, Escherichia coli K4, Pasteurella multocida (Q9CMP0)
Osawa, T.; Sugiura, N.; Shimada, H.; Hirooka, R.; Tsuji, A.; Shirakawa, T.; Fukuyama, K.; Kimura, M.; Kimata, K.; Kakuta, Y.
Crystal structure of chondroitin polymerase from Escherichia coli K4
Biochem. Biophys. Res. Commun.
378
10-14
2009
Escherichia coli (Q8L0V4), Escherichia coli K4 (Q8L0V4), Escherichia coli K4
Sugiura, N.; Shimokata, S.; Minamisawa, T.; Hirabayashi, J.; Kimata, K.; Watanabe, H.
Sequential synthesis of chondroitin oligosaccharides by immobilized chondroitin polymerase mutants
Glycoconj. J.
25
521-530
2008
Escherichia coli, Escherichia coli K4
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