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

Word Map on EC 2.4.99.6
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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.4.99.6
-
RECOMMENDED NAME
GeneOntology No.
N-acetyllactosaminide alpha-2,3-sialyltransferase
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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-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
ABH and Lewis epitopes biosynthesis from type 2 precursor disaccharide
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biosynthesis of Lewis epitopes (H. pylori)
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Glycosaminoglycan biosynthesis - keratan sulfate
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Glycosphingolipid biosynthesis - lacto and neolacto series
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Mannose type O-glycan biosynthesis
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Metabolic pathways
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neolacto-series glycosphingolipids biosynthesis
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Other types of O-glycan biosynthesis
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terminal O-glycans residues modification (via type 2 precursor disaccharide)
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Various types of N-glycan biosynthesis
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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)
Acts on beta-D-galactosyl-1,4-N-acetyl-D-glucosaminyl termini on glycoprotein.
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
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
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
-
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
-
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)-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
-
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-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
-
-
-
-
?
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
-
-
-
-
?
CMP-N-acetylneuraminate + 2-nitrophenyl-beta-D-galactopyranoside
CMP + alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-2-nitrophenyl
show the reaction diagram
-
-
-
-
?
CMP-N-acetylneuraminate + 4-methylumbelliferyl beta-lactoside
CMP + ?
show the reaction diagram
-
-
-
?
CMP-N-acetylneuraminate + 4-methylumbelliferyl Lewisx
CMP + ?
show the reaction diagram
-
-
-
?
CMP-N-acetylneuraminate + 4-nitrophenyl-D-galactoside
CMP + alpha-N-acetylneuraminyl-2,3-beta-D-(1-O-(4-nitrophenyl)-galactopyranose)
show the reaction diagram
-
-
-
-
?
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
-
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
-
-
?
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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-
-
?
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
-
-
-
?
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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-
-
?
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
-
-
-
?
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
-
-
-
?
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
-
-
?
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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-
-
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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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-
-
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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
-
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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-
-
-
?
CMP-N-acetylneuraminate + Galbeta(1->4)GlcNAcbeta(1->3)Galbeta(1->4)GlcNAc-4-nitrophenyl
?
show the reaction diagram
-
15.21% activity compared to Galbeta(1->4)GlcNAcbeta(1->6)(4FGalbeta(1->3))GalNAc-OBn
-
-
?
CMP-N-acetylneuraminate + Galbeta(1->4)GlcNAcbeta(1->6)(4FGalbeta(1->3))GalNAc-OBn
?
show the reaction diagram
-
100% activity
-
-
?
CMP-N-acetylneuraminate + ganglioside GM1
CMP + ganglioside GM3
show the reaction diagram
-
-
-
?
CMP-N-acetylneuraminate + gangliotetraosylceramide
CMP + N-acetylneuraminyl-alpha-2,3-gangliotetraosylceramide
show the reaction diagram
-
-
-
?
CMP-N-acetylneuraminate + globopentaosylceramide
CMP + ?
show the reaction diagram
-
-
-
-
?
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
-
-
-
?
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
-
-
?
CMP-N-acetylneuraminate + MeO-4-Galbeta(1->4)GlcNAc-OBn
?
show the reaction diagram
-
15.56% activity compared to Galbeta(1->4)GlcNAcbeta(1->6)(4FGalbeta(1->3))GalNAc-OBn
-
-
?
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
-
-
?
CMP-N-acetylneuraminate + T-antigen
CMP + ?
show the reaction diagram
-
-
-
-
?
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
-
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
-
-
-
-
?
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
-
-
-
-
?
CMP-Neu5Ac + PA-LacNAc
?
show the reaction diagram
-
-
-
-
?
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)
-
-
?
CMP-NeuAc + 3-O-sulfo-D-Fucbeta1,3GalNAcbeta1,3Galalpha-OMe
?
show the reaction diagram
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-
-
-
?
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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-
-
-
?
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
-
-
-
-
?
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
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-
-
-
?
CMP-NeuAc + GalNAcbeta1,4(Fucalpha1,3)GlcNAcbeta1,6(Galbeta1,3)GalNAcalphaO-Me
?
show the reaction diagram
-
-
-
-
?
CMP-sialic acid + asialofetuin
?
show the reaction diagram
-
-
-
-
?
additional information
?
-
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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-
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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
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
assay mixture contains 30 mM MnCl2
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
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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
-
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
-
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, 37C, 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 22C
-
0.83
Galbeta(1->4)GlcNAcbeta(1->3)Gal-4-nitrophenyl
-
at pH 6.0 and 22C
-
0.027
gangliotetraosylceramide
-
pH 7.2, 37C
0.9
lacto-N-neohexaosylceramide
-
37C
additional information
additional information
-
-
-
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
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.9 - 34
4-methylumbelliferyl beta-lactoside
4392
0.32 - 1
4-methylumbelliferyl Lewisx
12237
0.018 - 73
CMP-N-acetylneuraminate
180
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
-
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
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
2.7
-
partially purified enzyme
additional information
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
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
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
-
assay at
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
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
80000
-
x * 80000, isoform ST2, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
4C, 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
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-70C, purified enzyme, over 50 days, isoform ST2 remains stable
-
4C, concentrated solution of recombinant enzyme, 6 months without loss of activity
-
4C, partially purified, in 20% v/v glycerol, at least 1 week, after Ultrogel AcA34 fractionation, t1/2: 24 h
-
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
-
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
-
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
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
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
drug development
-
the enzyme is a target for design of specific inhibitors
synthesis