Information on EC 2.4.99.6 - N-acetyllactosaminide alpha-2,3-sialyltransferase

for references in articles please use BRENDA:EC2.4.99.6
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The enzyme appears in viruses and cellular organisms

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EC NUMBER
COMMENTARY hide
2.4.99.6
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RECOMMENDED NAME
GeneOntology No.
N-acetyllactosaminide alpha-2,3-sialyltransferase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
CMP-N-acetyl-beta-neuraminate + beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-R = CMP + N-acetyl-alpha-neuraminyl-(2->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-R
show the reaction diagram
CMP-N-acetylneuraminate + beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-D-glucosyl-(1<->1)-ceramide = CMP + alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-D-glucosyl-(1<->1)-ceramide
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycosyl group transfer
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
biosynthesis of Lewis epitopes (H. pylori)
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ABH and Lewis epitopes biosynthesis from type 2 precursor disaccharide
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terminal O-glycans residues modification (via type 2 precursor disaccharide)
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neolacto-series glycosphingolipids biosynthesis
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Various types of N-glycan biosynthesis
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Other types of O-glycan biosynthesis
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Mannose type O-glycan biosynthesis
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Glycosaminoglycan biosynthesis - keratan sulfate
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Glycosphingolipid biosynthesis - lacto and neolacto series
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Metabolic pathways
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SYSTEMATIC NAME
IUBMB Comments
CMP-N-acetyl-beta-neuraminate:beta-D-galactosyl-(1->4)-N-acetyl-btea-D-glucosaminyl-R (2->3)-N-acetyl-alpha-neuraminyltransferase (configuration-inverting)
The enzyme recognizes the sequence beta-D-galactosyl-(1->4)-N-acetyl-D-glucosaminyl (known as type 2 histo-blood group precursor disaccharide) in non-reducing termini of glycan moieties in glycoproteins and glycolipids. The enzyme from chicken brain was shown to act on neolactotetraosylceramide, producing ganglioside LM1 [2].
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CAS REGISTRY NUMBER
COMMENTARY hide
77537-85-0
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83745-06-6
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
calf
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
brasilian strain, ATCC VR-115; from infected european rabbit RK13 cells
SwissProt
Manually annotated by BRENDA team
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
expression of isoform ST3Gal IV in gastrointestinal cell lines is correlated with the expression of sialyl Lewis x at the cell surface. Isoform ST3Gal IV leads to de novo synthesis of sialyl Lewis x determinant on different molecular weight glycoproteins of MKN45 cells; isoforms ST3Gal III leads to de novo synthesis of sialyl Lewis x determinant on different molecular weight glycoproteins of MKN45 cells
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
CMP-N-acetylneuraminate + 2-(trimethylsilyl)ethyl beta-D-galactopyranosyl-(1,3)-2-acetamido-2-deoxy-beta-D-galactopyranoside
CMP + 2-(trimethylsilyl)ethyl (5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylonic acid)-(2,3)-beta-D-galactopyranosyl-(1,3)-2-acetamido-2-deoxy-beta-D-galactopyranoside
show the reaction diagram
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the enzyme transfers sialyl residues to Galbeta(1-3)GlcNAc as well as to Galbeta(1-4)GlcNAc partial structures in gangliosides, thus making an allocation to EC 2.4.99.4 or EC 2.4.99.6 difficult
-
-
?
CMP-N-acetylneuraminate + 2-(trimethylsilyl)ethyl beta-D-galactopyranosyl-(1,3)-2-deoxy-2-trichloroacetamido-beta-D-galactopyranoside
CMP + 2-(trimethylsilyl)ethyl (5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylonic acid)-(2,3)-beta-D-galactopyranosyl-(1,3)-2-deoxy-2-trichloroacetamido-beta-D-galactopyranoside
show the reaction diagram
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the enzyme transfers sialyl residues to Galbeta(1-3)GlcNAc as well as to Galbeta(1-4)GlcNAc partial structures in gangliosides, thus making an allocation to EC 2.4.99.4 or EC 2.4.99.6 difficult
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-
?
CMP-N-acetylneuraminate + 2-(trimethylsilyl)ethyl beta-D-galactopyranosyl-(1,3)-beta-D-galactopyranoside
CMP + 2-(trimethylsilyl)ethyl (5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylonic acid)-(2,3)-beta-D-galactopyranosyl-(1,3)-beta-D-galactopyranoside
show the reaction diagram
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the enzyme transfers sialyl residues to Galbeta(1-3)GlcNAc as well as to Galbeta(1-4)GlcNAc partial structures in gangliosides, thus making an allocation to EC 2.4.99.4 or EC 2.4.99.6 difficult
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-
?
CMP-N-acetylneuraminate + 2-deoxy-beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl-glycoprotein
CMP + alpha-N-acetylneuraminyl-2,3-2-deoxy-beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl-glycoprotein
show the reaction diagram
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-
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?
CMP-N-acetylneuraminate + 2-deoxy-beta-D-galactosyl-1,4-N-propionyl-D-glucosaminyl-glycoprotein
CMP + alpha-N-acetylneuraminyl-2,3-2-deoxy-beta-D-galactosyl-1,4-N-propionyl-D-glucosaminyl-glycoprotein
show the reaction diagram
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-
-
-
?
CMP-N-acetylneuraminate + 2-nitrophenyl-beta-D-galactopyranoside
CMP + alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-2-nitrophenyl
show the reaction diagram
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-
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?
CMP-N-acetylneuraminate + 4-methylumbelliferyl beta-lactoside
CMP + ?
show the reaction diagram
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?
CMP-N-acetylneuraminate + 4-methylumbelliferyl Lewisx
CMP + ?
show the reaction diagram
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?
CMP-N-acetylneuraminate + 4-nitrophenyl-D-galactoside
CMP + alpha-N-acetylneuraminyl-2,3-beta-D-(1-O-(4-nitrophenyl)-galactopyranose)
show the reaction diagram
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?
CMP-N-acetylneuraminate + 6-(5-fluoresceincarboxamido)hexanoylsuccimidyl ester lactoside
CMP + ?
show the reaction diagram
CMP-N-acetylneuraminate + asialo-alpha1 acid glycoprotein
?
show the reaction diagram
CMP-N-acetylneuraminate + asialo-GM1
CMP + ?
show the reaction diagram
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?
CMP-N-acetylneuraminate + beta-D-galactopyranosyl-(1,3)-2-acetamido-2-deoxy-beta-D-glucopyranoside
CMP + 8-(methoxycarbonyl)octyl (5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylonic acid)-(2,3)-beta-D-galactopyranosyl-(1,3)-2-acetamido-2-deoxy-beta-D-glucopyranoside
show the reaction diagram
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the enzyme transfers sialyl residues to Galbeta(1-3)GlcNAc as well as to Galbeta(1-4)GlcNAc partial structures in gangliosides, thus making an allocation to EC 2.4.99.4 or EC 2.4.99.6 difficult
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-
?
CMP-N-acetylneuraminate + beta-D-galactopyranosyl-(1,4)-2-acetamido-2-deoxy-beta-D-glucopyranoside
CMP + 8-(methoxycarbonyl)octyl (5-acetamido-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylonic acid)-(2,3)-beta-D-galactopyranosyl-(1,4)-2-acetamido-2-deoxy-beta-D-glucopyranoside
show the reaction diagram
-
the enzyme transfers sialyl residues to Galbeta(1-3)GlcNAc as well as to Galbeta(1-4)GlcNAc partial structures in gangliosides, thus making an allocation to EC 2.4.99.4 or EC 2.4.99.6 difficult
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-
?
CMP-N-acetylneuraminate + beta-D-galactosyl-(1->3)-N-acetyl-alpha-D-galactosaminyl-R
CMP + alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-(1->3)-N-acetyl-alpha-D-galactosaminyl-R
show the reaction diagram
preferred substrate
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?
CMP-N-acetylneuraminate + beta-D-galactosyl-(1->4)-N-acetyl-alpha-D-galactosaminyl-R
?
show the reaction diagram
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-
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?
CMP-N-acetylneuraminate + beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-D-glucosyl-(1<->1)-ceramide
CMP + alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-D-glucosyl-(1<->1)-ceramide
show the reaction diagram
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-
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?
CMP-N-acetylneuraminate + beta-D-galactosyl-1,3-N-acetyl-D-glucosamine
CMP + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,4-N-acetyl-D-glucosamine
show the reaction diagram
CMP-N-acetylneuraminate + beta-D-galactosyl-1,4-beta-D-N-acetylglucosaminyl-1,6-beta-D-galactosyl-1,3-alpha-D-N-acetylgalactoaminyl-OR
CMP + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,4-beta-D-N-acetylglucosaminyl-1,6-beta-D-galactosyl-1,3-alpha-D-N-acetylgalactoaminyl-OR
show the reaction diagram
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-
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?
CMP-N-acetylneuraminate + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosaminyl-1,3-beta-D-galactosyl-1,4-D-glucosylceramide
CMP + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosaminyl-1,3-beta-D-galactosyl-1,4-D-glucosylceramide
show the reaction diagram
CMP-N-acetylneuraminate + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosaminyl-1,4-beta-D-galactosyl-1,4-beta-D-glucosyl-beta1-ceramide
CMP + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosaminyl-1,4-beta-D-galactosyl-1,4-beta-D-glucosyl-beta1-ceramide
show the reaction diagram
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i.e. paragloboside
i.e. alpha-2,3-sialylparagloboside
?
CMP-N-acetylneuraminate + beta-D-galactosyl-1,4-N-acetyl-D-glucosamine
CMP + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,4-N-acetyl-D-glucosamine
show the reaction diagram
CMP-N-acetylneuraminate + beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl-1,2-alpha-mannosyl-1,3-beta-mannosyl-1,4-N-acetyl-D-glucosamine
CMP + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl-1,2-alpha-mannosyl-1,3-beta-mannosyl-1,4-N-acetyl-D-glucosamine
show the reaction diagram
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-
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?
CMP-N-acetylneuraminate + beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl-1,2-alpha-mannosyl-1,6-beta-mannosyl-1,4-N-acetyl-D-glucosamine
CMP + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl-1,2-alpha-mannosyl-1,6-beta-mannosyl-1,4-N-acetyl-D-glucosamine
show the reaction diagram
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?
CMP-N-acetylneuraminate + beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl-1,O-2-(dimethyloctylsilyl)ethyl
CMP + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl-1,O-2-(dimethyloctylsilyl)ethyl
show the reaction diagram
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intermediate in the preparative production of gangliosides
?
CMP-N-acetylneuraminate + beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl-glycoprotein
CMP + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl-glycoprotein
show the reaction diagram
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?
CMP-N-acetylneuraminate + beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl-O(CH2)8CO2CH3
CMP + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl-O(CH2)8CO2CH3
show the reaction diagram
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?
CMP-N-acetylneuraminate + beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl-R
CMP + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl-R
show the reaction diagram
CMP-N-acetylneuraminate + beta-D-galactosyl-1,4-N-propionyl-D-glucosaminyl-glycoprotein
CMP + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,4-N-propionyl-D-glucosaminyl-glycoprotein
show the reaction diagram
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?
CMP-N-acetylneuraminate + Galbeta(1-4)GlcNAcbeta(1-2)Manalpha-(1-6/1-3))2Manbeta(1-4)GlcNAcbeta(1-4)GlcNAcbeta-1-asparagine-Fmoc
CMP + ?
show the reaction diagram
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?
CMP-N-acetylneuraminate + Galbeta(1->3)GlcNAcbeta(1->3)lac-4-nitrophenyl
?
show the reaction diagram
CMP-N-acetylneuraminate + Galbeta(1->4)(Fucalpha(1->3))GlcNAcbeta-OR
CMP + NeuAcalpha(2->3)Galbeta(1->4)(Fucalpha(1->3))GlcNAcbeta-OR
show the reaction diagram
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?
CMP-N-acetylneuraminate + Galbeta(1->4)Glc-NAcbeta(1->3)Gal-4-nitrophenyl
?
show the reaction diagram
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16.78% activity compared to Galbeta(1->4)GlcNAcbeta(1->6)(4FGalbeta(1->3))GalNAc-OBn
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?
CMP-N-acetylneuraminate + Galbeta(1->4)GlcNAcbeta(1->3)Gal-4-nitrophenyl
?
show the reaction diagram
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-
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?
CMP-N-acetylneuraminate + Galbeta(1->4)GlcNAcbeta(1->3)Galbeta(1->4)GlcNAc-4-nitrophenyl
?
show the reaction diagram
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15.21% activity compared to Galbeta(1->4)GlcNAcbeta(1->6)(4FGalbeta(1->3))GalNAc-OBn
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?
CMP-N-acetylneuraminate + Galbeta(1->4)GlcNAcbeta(1->6)(4FGalbeta(1->3))GalNAc-OBn
?
show the reaction diagram
-
100% activity
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?
CMP-N-acetylneuraminate + ganglioside GM1
CMP + ganglioside GM3
show the reaction diagram
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-
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?
CMP-N-acetylneuraminate + gangliotetraosylceramide
CMP + N-acetylneuraminyl-alpha-2,3-gangliotetraosylceramide
show the reaction diagram
-
-
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?
CMP-N-acetylneuraminate + globopentaosylceramide
CMP + ?
show the reaction diagram
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?
CMP-N-acetylneuraminate + GM1a
CMP + ?
show the reaction diagram
-
-
-
-
?
CMP-N-acetylneuraminate + GM3
CMP + ?
show the reaction diagram
CMP-N-acetylneuraminate + lacto-N-biose
CMP + ?
show the reaction diagram
CMP-N-acetylneuraminate + lacto-N-neohexaosylceramide
CMP + N-acetylneuraminyl-lacto-N-neohexaosylceramide
show the reaction diagram
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-
-
?
CMP-N-acetylneuraminate + lactose
CMP + ?
show the reaction diagram
CMP-N-acetylneuraminate + MeO-2-Galbeta(1->3)GlcNAc-OBn
?
show the reaction diagram
-
32.88% activity compared to Galbeta(1->4)GlcNAcbeta(1->6)(4FGalbeta(1->3))GalNAc-OBn
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?
CMP-N-acetylneuraminate + MeO-4-Galbeta(1->4)GlcNAc-OBn
?
show the reaction diagram
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15.56% activity compared to Galbeta(1->4)GlcNAcbeta(1->6)(4FGalbeta(1->3))GalNAc-OBn
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-
?
CMP-N-acetylneuraminate + N-acetyllactosamine
CMP + ?
show the reaction diagram
CMP-N-acetylneuraminate + neolactotetraosylceramide
CMP + sialyl paragloboside
show the reaction diagram
-
-
-
?
CMP-N-acetylneuraminate + nLc4Cer
CMP + Neu-5-NAc-nLc4Cer
show the reaction diagram
low activity, at least 1 mM substrate concentration required
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-
?
CMP-N-acetylneuraminate + T-antigen
CMP + ?
show the reaction diagram
-
-
-
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?
CMP-Neu5Ac + 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-alpha-D-glucopyranosyl bromide
CMP + ?
show the reaction diagram
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64% of the activity with CMP-Neu5Ac + 6-(dansyl)-aminohexyl O-beta-D-galactopyranosyl-(1,3)-(2-acetamido-2-deoxy-beta-D-glucopyranoside)
-
-
?
CMP-Neu5Ac + 6-(dansyl)-aminohexyl O-beta-D-galactopyranosyl-(1,3)-(2-acetamido-2-deoxy-beta-D-glucopyranoside)
CMP + 6-(dansyl)-aminohexyl (5-acetamido-3,5-dideoxy-alpha-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2,3)-O-beta-D-galactopyranosyl-(1,3)-2-acetamido-2-deoxy-beta-D-glucopyranoside
show the reaction diagram
-
-
-
-
?
CMP-Neu5Ac + asialofetuin
CMP + fetuin
show the reaction diagram
-
-
-
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?
CMP-Neu5Ac + beta-D-Galp-(1-4)-beta-D-GlcpNAc-(1-2)-alpha-D-Manp-O-CH3
CMP + alpha-Neu5Ac-(2-6)-beta-D-Galp-(1-4)-beta-D-GlcpNAc-(1-2)-alpha-D-Manp-O-CH3
show the reaction diagram
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-
-
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?
CMP-Neu5Ac + PA-LacNAc
?
show the reaction diagram
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-
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?
CMP-Neu5Gc + 6-(dansyl)-aminohexyl O-beta-D-galactopyranosyl-(1,3)-(2-acetamido-2-deoxy-beta-D-glucopyranoside)
CMP + ?
show the reaction diagram
-
28% of the activity with CMP-Neu5Ac + 6-(dansyl)-aminohexyl O-beta-D-galactopyranosyl-(1,3)-(2-acetamido-2-deoxy-beta-D-glucopyranoside)
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?
CMP-NeuAc + 3-O-sulfo-D-Fucbeta1,3GalNAcbeta1,3Galalpha-OMe
?
show the reaction diagram
-
-
-
-
?
CMP-NeuAc + D-Fucbeta1,3GalNAcbeta1,3Galalpha-O-Me
?
show the reaction diagram
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-
-
-
?
CMP-NeuAc + Galbeta-1,3-Galbeta-OC6H4NO2-p
CMP + Neualpha-2,3-Galbeta-1,3-Galbeta-OC6H4NO2-
show the reaction diagram
-
low activity, substrate of EC 2.4.99.4
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-
?
CMP-NeuAc + Galbeta-1,3-Glcbeta-OC6H4NO2-p
CMP + Neualpha-2,3-Galbeta-1,3-Glcbeta-OC6H4NO2-
show the reaction diagram
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-
-
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?
CMP-NeuAc + Galbeta-1,4-Galbeta-OC6H4NO2-p
CMP + Neualpha-2,3-Galbeta-1,4-Galbeta-OC6H4NO2-p
show the reaction diagram
-
-
-
-
?
CMP-NeuAc + Galbeta-1,4-Glcbeta-OC6H4NO2-p
CMP + Neualpha-2,3-Galbeta-1,4-Glcbeta-OC6H4NO2-p
show the reaction diagram
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-
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-
?
CMP-NeuAc + Galbeta-1,4-GlcNAcbeta-OC6H4NO2-p
CMP + Neualpha-2,3-Galbeta-1,4-GlcNAcbeta-OC6H4NO2-p
show the reaction diagram
-
best substrate
-
-
?
CMP-NeuAc + Galbeta1,4(Fucalpha1,3)GlcNAcbeta1,6(Galbeta1,3)GalNAcalphaO-Me
?
show the reaction diagram
-
-
-
-
?
CMP-NeuAc + GalNAcbeta1,4(Fucalpha1,3)GlcNAcbeta1,6(Galbeta1,3)GalNAcalphaO-Me
?
show the reaction diagram
-
-
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-
?
CMP-sialic acid + asialofetuin
?
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
CMP-N-acetylneuraminate + beta-D-galactosyl-(1->3)-N-acetyl-alpha-D-galactosaminyl-R
CMP + alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-(1->3)-N-acetyl-alpha-D-galactosaminyl-R
show the reaction diagram
I6WCL0
preferred substrate
-
-
?
CMP-N-acetylneuraminate + beta-D-galactosyl-(1->4)-N-acetyl-alpha-D-galactosaminyl-R
?
show the reaction diagram
I6WCL0
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-
-
?
CMP-N-acetylneuraminate + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosaminyl-1,3-beta-D-galactosyl-1,4-D-glucosylceramide
CMP + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosaminyl-1,3-beta-D-galactosyl-1,4-D-glucosylceramide
show the reaction diagram
-
involved in glycosphingolipid biosynthesis
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CMP-N-acetylneuraminate + beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl-glycoprotein
CMP + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl-glycoprotein
show the reaction diagram
-
-
-
-
?
CMP-N-acetylneuraminate + beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl-R
CMP + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl-R
show the reaction diagram
additional information
?
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
assay mixture contains 30 mM MnCl2
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(3alpha,5beta)-24-[4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl]cholan-3-ol
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IC50: 0.100 mM
2-(diethoxyphosphoryl)-3-[1-[(3alpha,5beta)-3-hydroxycholan-24-yl]-1H-1,2,3-triazol-4-yl]propanoic acid
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IC50: 0.007 mM
3-oxo-5beta-cholan-24-oic acid
-
IC50: 0.139 mM
3-[1-[(3alpha,5beta)-3-hydroxycholan-24-yl]-1H-1,2,3-triazol-4-yl]alanine
-
IC50: 0.083 mM
3-[1-[(3alpha,5beta)-3-hydroxycholan-24-yl]-1H-1,2,3-triazol-4-yl]propanoic acid
-
IC50: 0.010 mM
3alpha-D-aspartyl-5beta-cholan-24-oic acid
-
IC50: 0.006 mM
3alpha-L-aspartyl-5beta-cholan-24-oic acid
-
IC50: 0.012 mM
3alpha-succinyl-5beta-cholan-24-oic acid
-
IC50: 0.012 mM
3alpha-succinyl-5beta-cholan-24-oic acid carboxymethyl ester
-
IC50: 0.022 mM
3alpha-succinyl-5beta-cholan-24-oic acid tert-butyl ester
-
IC50: 0.013 mM
3beta-D-aspartyl-androstan-17-one
-
IC50: 0.480 mM
3beta-succinyl-androstan-17-one
-
IC50: 0.450 mM
4-[1-[(3alpha,5beta)-3-hydroxycholan-24-yl]-1H-1,2,3-triazol-4-yl]butanoic acid
-
noncompetitive inhibition, IC50: 0.005 mM
ammonium cytidin-5'-yl 2-[5-acetamido-2,6-anhydro-3,5-dideoxy-1-(ammonium (methyl-D-galactopyranosid-6-yl)phosphate)-D-erythro-L-gluco-nonitol-2-yl]ethylphosphonate
-
IC50: 1.3 mM
androstan-17-one 3beta-phosphate
-
IC50: 0.400 mM
cholane-3alpha,24-diol
-
IC50: 0.351 mM
CMP-N-acetylneuraminate
-
i.e. substrate inhibition by CMP-sialic acid
cytidin-5'-yl sialylethylphosphonate
-
i.e. sodium cytidin-5'-yl 2-(sodium 5-acetamido-2,6-anhydro-3,5-dideoxy-D-erythro-L-gluco-nonanoate-2-yl)ethylphosphonate, IC50: 0.047 mM
diphenyl [3alpha-hydroxy-5beta-ycholan-24-yl]phosphonate
-
IC50: 0.100 mM
epiandrosterone succinyl ester
-
-
lithocholic acid
-
non-competitive inhibition
N-ethylmaleimide
-
-
N-[(3alpha,5beta)-3-[(3-carboxypropanoyl)oxy]-24-oxocholan-24-yl]-L-aspartic acid
-
IC50: 0.018 mM
N-[3alpha-hydroxy-24-oxo-5beta-cholan-24-yl]-L-aspartic acid
-
IC50: 0.016 mM
N-[3alpha-hydroxy-24-oxo-5beta-cholan-24-yl]glycine
-
IC50: 0.025 mM
neolactotetraosylceramide
-
substrate inhibition
sialic acid
-
i.e. acetylneuraminate
sodium cytidin-5'-yl 2-(5-acetamido-2,6-anhydro-1-(sodium ethyl phosphate)-3,5-dideoxy-D-erythro-L-glucononitol-2-yl)ethylphosphonate
-
IC50: 0.95 mM
sodium cytidin-5'-yl 2-(5-acetamido-2,6-anhydro-3,5-dideoxy-D-erythro-L-gluco-nonanoate-2-yl)ethylphosphonate
-
IC50: 3.3 mM
sodium cytidin-5'-yl 2-(5-acetamido-2,6-anhydro-3,5-dideoxy-D-erythro-L-gluco-nonitol-2-yl)ethylphosphonate
-
IC50: 4.2 mM
soyasaponin I
-
a rigid pentacyclic system with trisaccharide from soybean saponin, in vitro and in vivo inhibition
Triton CF-54
-
additional information
-
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Triton CF-54
-
-
Triton CF-54/X-100
-
Triton DF-16
-
can replace Triton CF-54
-
Triton N-57
-
can replace Triton CF-54
-
Triton X-100
Tween 20
-
40% as efficient as Triton CF-54
Tween 60
-
27% as efficient as Triton CF-54
Tween 80
-
40% as efficient as Triton CF-54
additional information
-
no activation by Triton GR-7M, TW-30 or sodium taurocholate
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.995
2-(trimethylsilyl)ethyl beta-D-galactopyranosyl-(1,3)-2-acetamido-2-deoxy-beta-D-galactopyranoside
-
-
0.812
2-(trimethylsilyl)ethyl beta-D-galactopyranosyl-(1,3)-2-deoxy-2-trichloroacetamido-beta-D-galactopyranoside
-
-
0.99
2-(trimethylsilyl)ethyl beta-D-galactopyranosyl-(1,3)-beta-D-galactopyranoside
-
-
0.79 - 12
4-methylumbelliferyl beta-lactoside
8.1 - 17
4-methylumbelliferyl Lewisx
0.06608
beta-D-galactopyranosyl-(1,3)-2-acetamido-2-deoxy-beta-D-glucopyranoside
-
-
0.08761
beta-D-galactopyranosyl-(1,4)-2-acetamido-2-deoxy-beta-D-glucopyranoside
-
-
0.5
beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosaminyl-1,3-beta-D-galactosyl-1,4-D-glucosylceramide
-
pH 6.4, 37°C, neolactotetraosylceramide as substrate
0.11
beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl-O(CH2)8CO2CH3
-
0.3 - 13
CMP-N-acetylneuraminate
0.13
Galbeta(1->3)GlcNAcbeta(1->3)Lac-4-nitrophenyl
-
at pH 6.0 and 22°C
-
0.83
Galbeta(1->4)GlcNAcbeta(1->3)Gal-4-nitrophenyl
-
at pH 6.0 and 22°C
-
0.027
gangliotetraosylceramide
-
pH 7.2, 37°C
0.9
lacto-N-neohexaosylceramide
-
37°C
additional information
additional information
-
-
-
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
21 - 47
4-methylumbelliferyl beta-lactoside
4 - 8.4
4-methylumbelliferyl Lewisx
0.025 - 71
CMP-N-acetylneuraminate
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.9 - 34
4-methylumbelliferyl beta-lactoside
0.32 - 1
4-methylumbelliferyl Lewisx
0.018 - 73
CMP-N-acetylneuraminate
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0022
4-[1-[(3alpha,5beta)-3-hydroxycholan-24-yl]-1H-1,2,3-triazol-4-yl]butanoic acid
-
-
0.35
epiandrosterone succinyl ester
-
-
0.021
lithocholic acid
-
-
0.0021
soyasaponin I
-
-
additional information
additional information
-
kinetics
-
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.1
(3alpha,5beta)-24-[4-(2-hydroxyethyl)-1H-1,2,3-triazol-1-yl]cholan-3-ol
Rattus norvegicus;
-
IC50: 0.100 mM
0.007
2-(diethoxyphosphoryl)-3-[1-[(3alpha,5beta)-3-hydroxycholan-24-yl]-1H-1,2,3-triazol-4-yl]propanoic acid
Rattus norvegicus;
-
IC50: 0.007 mM
0.139
3-oxo-5beta-cholan-24-oic acid
Rattus norvegicus;
-
IC50: 0.139 mM
0.083
3-[1-[(3alpha,5beta)-3-hydroxycholan-24-yl]-1H-1,2,3-triazol-4-yl]alanine
Rattus norvegicus;
-
IC50: 0.083 mM
0.01
3-[1-[(3alpha,5beta)-3-hydroxycholan-24-yl]-1H-1,2,3-triazol-4-yl]propanoic acid
Rattus norvegicus;
-
IC50: 0.010 mM
0.006
3alpha-D-aspartyl-5beta-cholan-24-oic acid
Rattus norvegicus;
-
IC50: 0.006 mM
0.012
3alpha-L-aspartyl-5beta-cholan-24-oic acid
Rattus norvegicus;
-
IC50: 0.012 mM
0.012
3alpha-succinyl-5beta-cholan-24-oic acid
Rattus norvegicus;
-
IC50: 0.012 mM
0.022
3alpha-succinyl-5beta-cholan-24-oic acid carboxymethyl ester
Rattus norvegicus;
-
IC50: 0.022 mM
0.013
3alpha-succinyl-5beta-cholan-24-oic acid tert-butyl ester
Rattus norvegicus;
-
IC50: 0.013 mM
0.48
3beta-D-aspartyl-androstan-17-one
Rattus norvegicus;
-
IC50: 0.480 mM
0.45
3beta-succinyl-androstan-17-one
Rattus norvegicus;
-
IC50: 0.450 mM
0.005
4-[1-[(3alpha,5beta)-3-hydroxycholan-24-yl]-1H-1,2,3-triazol-4-yl]butanoic acid
Rattus norvegicus;
-
noncompetitive inhibition, IC50: 0.005 mM
1.3
ammonium cytidin-5'-yl 2-[5-acetamido-2,6-anhydro-3,5-dideoxy-1-(ammonium (methyl-D-galactopyranosid-6-yl)phosphate)-D-erythro-L-gluco-nonitol-2-yl]ethylphosphonate
Rattus norvegicus;
-
IC50: 1.3 mM
0.4
androstan-17-one 3beta-phosphate
Rattus norvegicus;
-
IC50: 0.400 mM
0.351
cholane-3alpha,24-diol
Rattus norvegicus;
-
IC50: 0.351 mM
0.047
cytidin-5'-yl sialylethylphosphonate
Rattus norvegicus;
-
i.e. sodium cytidin-5'-yl 2-(sodium 5-acetamido-2,6-anhydro-3,5-dideoxy-D-erythro-L-gluco-nonanoate-2-yl)ethylphosphonate, IC50: 0.047 mM
0.1
diphenyl [3alpha-hydroxy-5beta-ycholan-24-yl]phosphonate
Rattus norvegicus;
-
IC50: 0.100 mM
0.018
N-[(3alpha,5beta)-3-[(3-carboxypropanoyl)oxy]-24-oxocholan-24-yl]-L-aspartic acid
Rattus norvegicus;
-
IC50: 0.018 mM
0.016
N-[3alpha-hydroxy-24-oxo-5beta-cholan-24-yl]-L-aspartic acid
Rattus norvegicus;
-
IC50: 0.016 mM
0.025
N-[3alpha-hydroxy-24-oxo-5beta-cholan-24-yl]glycine
Rattus norvegicus;
-
IC50: 0.025 mM
0.95
sodium cytidin-5'-yl 2-(5-acetamido-2,6-anhydro-1-(sodium ethyl phosphate)-3,5-dideoxy-D-erythro-L-glucononitol-2-yl)ethylphosphonate
Rattus norvegicus;
-
IC50: 0.95 mM
3.3
sodium cytidin-5'-yl 2-(5-acetamido-2,6-anhydro-3,5-dideoxy-D-erythro-L-gluco-nonanoate-2-yl)ethylphosphonate
Rattus norvegicus;
-
IC50: 3.3 mM
4.2
sodium cytidin-5'-yl 2-(5-acetamido-2,6-anhydro-3,5-dideoxy-D-erythro-L-gluco-nonitol-2-yl)ethylphosphonate
Rattus norvegicus;
-
IC50: 4.2 mM
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
2.7
-
partially purified enzyme
additional information
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.2
-
assay at
6.7
-
assay at
6.8
-
in the presence of Triton CF-54 and Mg2+
7.4
-
assay at
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.8 - 7.2
-
about half-maximal activity at pH 5.8 and about 90% of maximal activity at pH 7.2
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
-
assay at
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
pancreatic adenocarcinoma cell line, enzyme expression and activity, overview
Manually annotated by BRENDA team
developmental regulation
Manually annotated by BRENDA team
developmental regulation
Manually annotated by BRENDA team
-
from peripheral blood mononuclear cells, enzyme level stimulated by phytohemagglutinin
Manually annotated by BRENDA team
-
pancreatic adenocarcinoma cell line, enzyme expression and activity, overview
Manually annotated by BRENDA team
-
pancreatic adenocarcinoma cell line, enzyme expression and activity, overview
Manually annotated by BRENDA team
-
high; high activity
Manually annotated by BRENDA team
-
pancreatic adenocarcinoma cell line, enzyme expression and activity, overview
Manually annotated by BRENDA team
-
four pancreatic adenocarcinoma cell lines of a wide range of neoplastic differentiation stages, ST3Gal III and ST3Gal IV expression and activity, overview
Manually annotated by BRENDA team
additional information
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
80000
-
x * 80000, isoform ST2, SDS-PAGE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
4°C, enzyme immobilized on Nickel charged Agarose beads via the His6-tag is stable for at least 5 months, crude culture supernatants are inactivated in 2 weeks
-
fractionation on Ultrogel AcA34 decreases activity, bovine serum albumin restores
-
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-70°C, purified enzyme, over 50 days, isoform ST2 remains stable
-
4°C, concentrated solution of recombinant enzyme, 6 months without loss of activity
-
4°C, partially purified, in 20% v/v glycerol, at least 1 week, after Ultrogel AcA34 fractionation, t1/2: 24 h
-
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
amylose column chromatography
-
HisTrap column chromatography
-
Ni2+-affinity column chromatography
partial, CDP-ethanolamine-Sepharose affinity chromatography
-
partial, using centrifugation in a sucrose gradient
-
partial, using DEAE-Cibacron Blue chromatography after sodium taurocholate solubilization
-
partially purified from host cell lysate
purification of a recombinant GST fusion protein using glutathione-agarose affinity chromatography
-
recombinant from COS-7 cells
recombinant soluble enzyme from the medium of baculovirus transfected Spodoptera frugiperda SF9 cells, partially
-
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis, expression in COS-7 cells, fused to staphylococcal protein A
expressed in 293FT cells
-
expressed in CHO and HEK-293T cells
-
expressed in Escherichia coli
-
expressed in Escherichia coli AD202 cells
-
expressed in Escherichia coli BL21(DE3) cells
expression as soluble enzyme under control of the late viral polyhedron promotor in Spodoptera frugiperda Sf9 cells via baculovirus infection
-
expression from baculovirus infected Sf9 insect cells in preparative amounts
-
expression in Cos-1 cells
-
expression of a GST fusion protein in Escherichia coli
-
expression of soluble ST3Gal-III in Sf9 cells
-
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
cyclooxygenase-2 upregulates the expression of isoform alpha-2,3-sialyltransferase-3 in breast cancer. 12-O-tetradecanoylphorbol-13-acetate and prostaglandin E2 (0.001 mM) can induce the expression of ST3Gal-I in the breast cancer cell line T-47
in gastric adenocarcinoma cells, isoform ST3GalIII mRNA expression is 6fold increased; in gastric adenocarcinoma cells, isoform ST3GalIV mRNA expression is increased 1000fold; in gastric adenocarcinoma cells, isoform ST3GalVI mRNA expression is 32000fold increased
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
H284D
-
the mutant shows reduced activity compared to the wild type enzyme
H284N
-
the mutant shows reduced activity compared to the wild type enzyme
H284Y
-
the mutant shows reduced activity compared to the wild type enzyme
D141A
the mutation results in 1000fold decrease in the efficiency of alpha2-3-sialyltransferase activity
E271F/R313Y
the mutant does not efficiently sialylate fucose-containing oligosaccharides such as Lex
H311A
the mutation results in 16fold decrease in the efficiency of alpha2-3-sialyltransferase activity
M144D
the mutant shows 20000fold decreased donor hydrolysis activity without significantly affecting its alpha2-3-sialylation activity when a poor fucose-containing acceptor substrate is used
M144H
the mutation results in 3fold decrease in the efficiency of alpha2-3-sialyltransferase activity
additional information
-
construction of a nonpolar alpha-2,3-sialyltransferase lst mutant, which is significantly attenuated in its capacity to colonize the lower genital tract of 17-beta estradiol-treated female BALB/c mice during competitive infection with the wild-type strain, genetic complementation of the lst mutation restores recovery of the mutant to wild-type levels, attenuation of the lst mutant is not due to increased sensitivity to complement-mediated bacteriolysis, phenotype, overview
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
drug development
-
the enzyme is a target for design of specific inhibitors
synthesis
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LINKS TO OTHER DATABASES (specific for EC-Number 2.4.99.6)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
InterPro (database of protein families, domains and functional sites)