Information on EC 2.4.99.1 - beta-galactoside alpha-(2,6)-sialyltransferase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
2.4.99.1
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RECOMMENDED NAME
GeneOntology No.
beta-galactoside alpha-(2,6)-sialyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
CMP-N-acetyl-beta-neuraminate + beta-D-galactosyl-R = CMP + N-acetyl-alpha-neuraminyl-(2->6)-beta-D-galactosyl-R
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycosyl group transfer
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
ganglio-series glycosphingolipids biosynthesis
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lacto-series glycosphingolipids biosynthesis
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Metabolic pathways
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N-Glycan biosynthesis
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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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SYSTEMATIC NAME
IUBMB Comments
CMP-N-acetyl-beta-neuraminate:beta-D-galactoside alpha-(2->6)-N-acetylneuraminyltransferase (configuration-inverting)
The terminal beta-D-galactosyl residue of the oligosaccharide of glycoproteins, as well as lactose, can act as acceptor.
CAS REGISTRY NUMBER
COMMENTARY hide
55071-95-9
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9075-81-4
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
fragment
SwissProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
C57BL/6 mice
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Manually annotated by BRENDA team
cichlid fish
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Manually annotated by BRENDA team
strain JT-SHIZ-119
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Manually annotated by BRENDA team
ST6GAL2, fragment; i.e. Silurana tropicalis, western clawed frog
SwissProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
asialo-alpha1-acidglycoprotein + CMP-Neu5Ac
?
show the reaction diagram
membrane-bound and soluble protein, 34% and 25% relative activity, respectively
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?
CMP-9''-benzamido-Neu5Ac + lactose
?
show the reaction diagram
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?
CMP-9''-benzamido-Neu5Ac + N-acetyllactosamine
?
show the reaction diagram
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-
-
-
?
CMP-9''-phenylacetamido-Neu5Ac + lactose
?
show the reaction diagram
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-
-
-
?
CMP-9''-phenylacetamido-Neu5Ac + N-acetyllactosamine
?
show the reaction diagram
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-
-
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?
CMP-9''-phenylhexanamido-Neu5Ac + lactose
?
show the reaction diagram
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-
-
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?
CMP-9''-phenylhexanamido-Neu5Ac + N-acetyllactosamine
?
show the reaction diagram
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?
CMP-9''-phenylpropionamido-Neu5Ac + lactose
?
show the reaction diagram
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-
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?
CMP-9''-phenylpropionamido-Neu5Ac + N-acetyllactosamine
?
show the reaction diagram
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-
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?
CMP-9-acetamido-N-acetylneuraminate + asialo-alpha1-acid glycoprotein
?
show the reaction diagram
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-
-
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?
CMP-9-amino-N-acetylneuraminate + asialo-alpha1-acid glycoprotein
?
show the reaction diagram
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-
-
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?
CMP-9-azido-N-acetylneuraminate + asialo-alpha1-acid glycoprotein
?
show the reaction diagram
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-
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?
CMP-9-benzamido-N-acetylneuraminate + asialo-alpha1-acid glycoprotein
?
show the reaction diagram
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-
-
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?
CMP-9-fluoresceinyl-N-acetylneuraminate + asialofetuin
?
show the reaction diagram
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-
-
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?
CMP-9-hexanoylamido-N-acetylneuraminate + asialo-alpha1-acid glycoprotein
?
show the reaction diagram
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-
-
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?
CMP-9-O-acetyl-N-acetylneuraminate + asialo-alpha1-acid glycoprotein
?
show the reaction diagram
CMP-9-O-acetyl-N-acetylneuraminate + asialo-alpha1-acid glycoprotein
CMP + ?
show the reaction diagram
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-
-
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?
CMP-N-acetylneuraminate + (2S,3S,4R,5R,6R)-5-acetylamino-4-hydroxy-6-methoxy-3-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
CMP + ?
show the reaction diagram
CMP-N-acetylneuraminate + (2S,3S,4R,5R,6R)-5-acetylamino-4-hydroxy-6-methoxy-3-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methylamide
CMP + ?
show the reaction diagram
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0.2% of the activity with Galbeta(1-3)GlcNAcbeta-O-Me
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?
CMP-N-acetylneuraminate + (Gal-3-O-Me)beta(1-3)(GlcNAc-6-O-Me)beta-O-Me
CMP + ?
show the reaction diagram
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50% of the activity with Galbeta(1-3)GlcNAcbeta-O-Me
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?
CMP-N-acetylneuraminate + (Gal-3-O-Me)beta(1-3)GlcNAcbeta-O-Me
CMP + ?
show the reaction diagram
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80% of the activity with Galbeta(1-3)GlcNAcbeta-O-Me
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?
CMP-N-acetylneuraminate + (Galbeta(1,4))2(GlcNAcbeta(1,2))2(Man)3(GlcNAc)2-Asn-Fmoc
?
show the reaction diagram
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34.9 activity compared to Galbeta(1,4)-GlcNAcbeta-4-nitrophenyl
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?
CMP-N-acetylneuraminate + (GalNAcbeta(1,4))2(GlcNAcbeta(1,2))2(Man)3(GlcNAc)2-Asn-Fmoc
?
show the reaction diagram
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140 activity compared to Galbeta(1,4)-GlcNAcbeta-4-nitrophenyl
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?
CMP-N-acetylneuraminate + 4-methylumbelliferyl beta-D-lactoside
?
show the reaction diagram
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?
CMP-N-acetylneuraminate + 4-nitrophenyl-D-galactoside
CMP + alpha-N-acetylneuraminyl-2,6-beta-D-galactosyl-(4-nitro)phenol
show the reaction diagram
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?
CMP-N-acetylneuraminate + 5-(5-dimethylaminonaphthalene-1-sulfonyl-2-(2-aminoethoxy))ethyl beta-lactose
CMP + ?
show the reaction diagram
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?
CMP-N-acetylneuraminate + 5-(5-dimethylaminonaphthalene-1-sulfonyl-2-(2-aminoethoxy))ethyl beta-N-acetyllactosamine
CMP + 5-(5-dimethylaminonaphthalene-1-sulfonyl-2-(2-aminoethoxy)) ethyl beta-N-acetylneuraminic acid alpha-2,6-N-acetyllactosamine
show the reaction diagram
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?
CMP-N-acetylneuraminate + 6'-sialyl-N-acetyl-D-lactosamine
?
show the reaction diagram
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?
CMP-N-acetylneuraminate + AA-labeled 6'-sialyllactose
?
show the reaction diagram
CMP-N-acetylneuraminate + AA-labeled G2 glycan
?
show the reaction diagram
CMP-N-acetylneuraminate + alpha1-acid glycoprotein
CMP + ?
show the reaction diagram
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20.6% of the activity with beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine
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?
CMP-N-acetylneuraminate + asialo-agalacto-prothrombin
CMP + agalacto-prothrombin
show the reaction diagram
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?
CMP-N-acetylneuraminate + asialo-alpha1-acid glycoprotein
CMP + ?
show the reaction diagram
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12.3% of the activity with beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine
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?
CMP-N-acetylneuraminate + asialo-alpha1-acid glycoprotein
CMP + alpha1-acid glycoprotein
show the reaction diagram
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176% of the activity with beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine
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?
CMP-N-acetylneuraminate + asialo-apoceruloplasmin
CMP + apoceruloplasmin
show the reaction diagram
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best substrate
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?
CMP-N-acetylneuraminate + asialo-ceruloplasmin
CMP + ceruloplasmin
show the reaction diagram
CMP-N-acetylneuraminate + asialo-chorionic gonadotropin
CMP + chorionic gonadotropin
show the reaction diagram
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acceptor protein from human source
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?
CMP-N-acetylneuraminate + asialo-fetuin
CMP + fetuin
show the reaction diagram
CMP-N-acetylneuraminate + asialo-fibrinogen
CMP + fibrinogen
show the reaction diagram
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?
CMP-N-acetylneuraminate + asialo-immunoglobulin G
CMP + immunoglobulin G
show the reaction diagram
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?
CMP-N-acetylneuraminate + asialo-immunoglobulin M
CMP + immunoglobulin M
show the reaction diagram
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?
CMP-N-acetylneuraminate + asialo-orosomucoid
CMP + orosomucoid
show the reaction diagram
CMP-N-acetylneuraminate + asialo-proteose peptone
CMP + proteose peptone
show the reaction diagram
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?
CMP-N-acetylneuraminate + asialo-prothrombin
CMP + prothrombin
show the reaction diagram
CMP-N-acetylneuraminate + asialo-Tamm-Horsfall glycoprotein
CMP + Tamm-Horsfall glycoprotein
show the reaction diagram
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?
CMP-N-acetylneuraminate + asialo-thyroglobulin
CMP + thyroglobulin
show the reaction diagram
CMP-N-acetylneuraminate + asialo-thyroglobulin glycopeptide
CMP + thyroglobulin glycopeptide
show the reaction diagram
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?
CMP-N-acetylneuraminate + asialo-transferrin
CMP + transferrin
show the reaction diagram
CMP-N-acetylneuraminate + asialofetuin
?
show the reaction diagram
CMP-N-acetylneuraminate + asialoovomucoid
CMP + ?
show the reaction diagram
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9.1% of the activity with beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine
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?
CMP-N-acetylneuraminate + beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosamine
CMP + alpha-N-acetylneuraminyl-(2->6)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosamine
show the reaction diagram
CMP-N-acetylneuraminate + beta-D-galactosyl-1,3-N-acetyl-beta-D-glucosamine
CMP + alpha-N-acetylneuraminyl-2,6-beta-D-galactosyl-1,3-N-acetyl-beta-D-glucosamine
show the reaction diagram
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36% of the activity with beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine
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?
CMP-N-acetylneuraminate + beta-D-galactosyl-1,3-N-acetyl-beta-D-glucosaminyl-1,3-galactosyl-beta-1,4-D-glucose
CMP + alpha-N-acetylneuraminyl-2,6-beta-D-galactosyl-1,3-N-acetyl-beta-D-glucosaminyl-1,3-galactosyl-beta-1,4-D-glucose
show the reaction diagram
CMP-N-acetylneuraminate + beta-D-galactosyl-1,4-beta-D-glucosylceramide
CMP + alpha-N-acetylneuraminyl-2,6-beta-D-galactosyl-1,4-beta-D-glucosylceramide
show the reaction diagram
CMP-N-acetylneuraminate + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine
CMP + alpha-N-acetylneuraminyl-2,6-beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine
show the reaction diagram
CMP-N-acetylneuraminate + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine-R
CMP + alpha-N-acetylneuraminyl-2,6-beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine-R
show the reaction diagram
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exhibits highest activity toward GalNAcbeta1,4GlcNAc carbohydrate structures at the non-reducing termini of oligosaccharides and glycoprotein glycans. Oligosaccharides are preferred over glycoproteins as acceptors, and no activity toward glycolipid acceptors is detected. Recombinant Drosophila SiaT expressed in cultured insect cells possesses in vivo and in vitro autosialylation activity toward beta-linked GalNAc termini of its own N-linked glycans
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?
CMP-N-acetylneuraminate + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosaminyl-1,2-alpha-mannosyl-1,6-beta-mannosyl-1,4-N-acetylglucosamine
CMP + alpha-N-acetylneuraminyl-2,6-beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosaminyl-1,2-alpha-mannosyl-1,6-beta-mannosyl-1,4-N-acetylglucosamine
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-1,4-beta-D-galactosyl-1,4-beta-D-glucosyl-beta1-ceramide
CMP + alpha-N-acetylneuraminyl-2,6-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-2,6-sialylparagloboside
?
CMP-N-acetylneuraminate + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosaminyl-R
CMP + alpha-N-acetylneuraminyl-2,6-beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosaminyl-R
show the reaction diagram
CMP-N-acetylneuraminate + fetuin
?
show the reaction diagram
CMP-N-acetylneuraminate + formic acid (2R,3R,4S,5R,6R)-2-((2R,3R,4R,5R,6R)-3-acetylamino-5-hydroxy-2-methoxy-6-methylaminomethyl-tetrahydro-pyran-4-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl ester
CMP + ?
show the reaction diagram
-
as active as Galbeta(1-3)GlcNAcbeta-O-Me
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?
CMP-N-acetylneuraminate + fucosyllactose
CMP + alpha-N-acetylneuraminyl-2,6-[alpha-L-fucopyranosyl-1,2]-beta-D-galactopyranosyl-1,4-D-glucopyranose
show the reaction diagram
-
also pyridylaminated
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?
CMP-N-acetylneuraminate + Gal-beta-1,3-GlcNAc-beta-OMe
?
show the reaction diagram
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77% of the activity with lactose
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?
CMP-N-acetylneuraminate + Galbeta(1,3)-GlcNAcbeta-4-nitrophenyl
?
show the reaction diagram
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2.5% activity compared to Galbeta(1,4)-GlcNAcbeta-4-nitrophenyl
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?
CMP-N-acetylneuraminate + Galbeta(1,4)-GlcNAcbeta-4-nitrophenyl
?
show the reaction diagram
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100% activity
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?
CMP-N-acetylneuraminate + Galbeta(1-3)(GlcNAc-6-O-Me)beta-O-Me
CMP + ?
show the reaction diagram
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80% of the activity with Galbeta(1-3)GlcNAcbeta-O-Me
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?
CMP-N-acetylneuraminate + Galbeta(1-3)-GlcNAcbeta(1-3)Galbeta(1-4)Glc
CMP + NeuNAcalpha(2-6)-Galbeta(1-3)GlcNAcbeta(1-3)Galbeta(1-4)Glc
show the reaction diagram
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30% of the activity with beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine
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-
?
CMP-N-acetylneuraminate + Galbeta(1-3)GlcNAcbeta-O-Me
CMP + NeuAcalpha(2-6)Galbeta(1-3)GlcNAcbeta-O-Me
show the reaction diagram
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-
-
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?
CMP-N-acetylneuraminate + Galbeta(1-4)GlcNAcbeta(1-3)Galbeta(1-4)Glc
CMP + alpha-N-acetylneuraminyl-(2-6)Galbeta(1-4)GlcNAcbeta(1-3)Galbeta(1-4)Glc
show the reaction diagram
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79% of the activity with beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine
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?
CMP-N-acetylneuraminate + Galbeta(1->3)GalNAc
CMP + NeuAcalpha(2->6)Galbeta(1->3)GalNAc
show the reaction diagram
10% activity compared to beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine
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-
?
CMP-N-acetylneuraminate + Galbeta(1->3)GlcNAc
CMP + NeuAcalpha(2->6)Galbeta(1->3)GlcNAc
show the reaction diagram
2% activity compared to beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine
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-
?
CMP-N-acetylneuraminate + Galbeta(1->4)GlcNAcbeta(1->2)Manalpha(1->6)[Galbeta(1->4)GlcNAcbeta(1>2)Manalpha(1->3)]Manbeta(1->4)GlcNAcbeta(1->4)GlcNAc-pyridylamine
CMP + NeuAcalpha(2->6)Galbeta(1->4)GlcNAcbeta(1->2)Manalpha(1->6)[Galbeta(1->4)GlcNAcbeta(1>2)Manalpha(1->3)]Manbeta(1->4)GlcNAcbeta(1->4)GlcNAc-pyridylamine
show the reaction diagram
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-
-
-
?
CMP-N-acetylneuraminate + Galbeta(1->4)GlcNAcbeta(1->3)Galbeta(1->4)Glcbeta(1<->1)ceramide
CMP + NeuAcalpha(2->6)Galbeta(1->4)GlcNAcbeta(1->3)Galbeta(1->4)Glcbeta(1<->1)ceramide
show the reaction diagram
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-
-
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?
CMP-N-acetylneuraminate + Galbeta-4-nitrophenyl
?
show the reaction diagram
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26.4% activity compared to Galbeta(1,4)-GlcNAcbeta-4-nitrophenyl
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?
CMP-N-acetylneuraminate + GalNAcbeta(1,4)-GlcNAcbeta-4-nitrophenyl
?
show the reaction diagram
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best acceptor with 371.5% activity compared to Galbeta(1,4)-GlcNAcbeta-4-nitrophenyl
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-
?
CMP-N-acetylneuraminate + GalNAcbeta-4-nitrophenyl
?
show the reaction diagram
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120.4% activity compared to Galbeta(1,4)-GlcNAcbeta-4-nitrophenyl
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-
?
CMP-N-acetylneuraminate + GalNAcbeta1,4-GlcNAc-R
CMP + alpha-N-acetylneuraminyl-2,6-GalNAcbeta1,4-GlcNAc-R
show the reaction diagram
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190% of the activity with beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine
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?
CMP-N-acetylneuraminate + lacto-N-neotetraose
?
show the reaction diagram
CMP-N-acetylneuraminate + lacto-N-neotetraose
CMP + ?
show the reaction diagram
108% activity compared to beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine
-
-
?
CMP-N-acetylneuraminate + lacto-N-tetraose
CMP + ?
show the reaction diagram
CMP-N-acetylneuraminate + lactosamine
?
show the reaction diagram
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-
-
-
?
CMP-N-acetylneuraminate + lactose
CMP + 6'-sialyllactose
show the reaction diagram
CMP-N-acetylneuraminate + lactose
CMP + alpha-N-acetylneuraminyl-2,6-beta-D-galactosyl-1,4-beta-D-glucose
show the reaction diagram
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15.5% of the activity with beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine
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-
?
CMP-N-acetylneuraminate + methanesulfonic acid (2R,3S,4R,5R,6R)-5-acetylamino-4-hydroxy-6-methoxy-3-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester
CMP + ?
show the reaction diagram
-
90% of the activity with Galbeta(1-3)GlcNAcbeta-O-Me
-
-
?
CMP-N-acetylneuraminate + methyl-alpha-D-galactopyranoside
?
show the reaction diagram
-
2% of the activity with lactose
-
-
?
CMP-N-acetylneuraminate + methyl-beta-D-galactopyranoside
?
show the reaction diagram
-
59% of the activity with lactose
-
-
?
CMP-N-acetylneuraminate + methyl-beta-D-galactopyranoside
CMP + alpha-N-acetylneuraminyl-2,6-beta-D-methylgalactopyranoside
show the reaction diagram
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-
-
-
?
CMP-N-acetylneuraminate + N-((1R,3R,5R,6R,7S,8R,13R,15R,16R,17S)-6,7,17-trihydroxy-5-hydroxymethyl-15-methoxy-2,4,9,11,14-pentaoxa-tricyclo[11.3.1.03,8]heptadec-16-yl)-acetamide
CMP + ?
show the reaction diagram
-
as active as Galbeta(1-3)GlcNAcbeta-O-Me
-
-
?
CMP-N-acetylneuraminate + N-((1R,3R,5R,6R,7S,8R,14R,16R,17R,18R)-6,7,18-trihydroxy-5-hydroxymethyl-16-methoxy-11-oxo-2,4,9,15-tetraoxa-12-aza-tricyclo[12.3.1.03,8]octadec-17-yl)-acetamide
CMP + ?
show the reaction diagram
-
110% of the activity with Galbeta(1-3)GlcNAcbeta-O-Me
-
-
?
CMP-N-acetylneuraminate + N-((1R,3R,5R,6R,7S,8R,14R,16R,17R,18S)-6,7,18-trihydroxy-5-hydroxymethyl-16-methoxy-2,4,9,12,15-pentaoxa-tricyclo[12.3.1.03,8]octadec-17-yl)-acetamide
CMP + ?
show the reaction diagram
-
130% of the activity with Galbeta(1-3)GlcNAcbeta-O-Me
-
-
?
CMP-N-acetylneuraminate + N-acetyl-D-galactosamine
?
show the reaction diagram
-
12% of the activity with lactose
-
-
?
CMP-N-acetylneuraminate + N-acetyllactosamine
?
show the reaction diagram
CMP-N-acetylneuraminate + N-[(2R,3R,4R,5S,6R)-4-hydroxy-6-(methanesulfonylamino-methyl)-2-methoxy-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
CMP + ?
show the reaction diagram
-
70% of the activity with Galbeta(1-3)GlcNAcbeta-O-Me
-
-
?
CMP-N-acetylneuraminate + N-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5R,6R)-4,5-dihydroxy-6-hydroxymethyl-3-methoxy-tetrahydro-pyran-2-yloxy)-6-formylaminomethyl-4-hydroxy-2-methoxy-tetrahydro-pyran-3-yl]-acetamide
CMP + ?
show the reaction diagram
-
as active as Galbeta(1-3)GlcNAcbeta-O-Me
-
-
?
CMP-N-acetylneuraminate + N-[(2R,3R,4R,5S,6R)-6-(acetylamino-methyl)-4-hydroxy-2-methoxy-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
CMP + ?
show the reaction diagram
-
60% of the activity with Galbeta(1-3)GlcNAcbeta-O-Me
-
-
?
CMP-N-acetylneuraminate + N-[(2R,3R,4R,5S,6R)-6-aminomethyl-4-hydroxy-2-methoxy-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
CMP + ?
show the reaction diagram
-
50% of the activity with Galbeta(1-3)GlcNAcbeta-O-Me
-
-
?
CMP-N-acetylneuraminate + Neu5Acalpha-2,3-Galbeta-1,4-Glc
CMP + alpha-N-acetylneuraminyl-2,6-(Neu5Acalpha-2,3-)Galbeta-1,4-Glc
show the reaction diagram
-
also pyridylaminated
-
-
?
CMP-N-acetylneuraminate + ovomucoid
CMP + ?
show the reaction diagram
-
8.4% of the activity with beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine
-
-
?
CMP-N-acetylneuraminate + pyridylamine-type 2H
CMP + alpha2,6-sialylated blood group type 2H antigen
show the reaction diagram
-
2% activity compared to pyridylaminyl-lacto-N-neotetraose
-
-
?
CMP-N-acetylneuraminate + pyridylamino-lactose
CMP + alpha-N-acetylneuraminyl-2,6-beta-D-galactosyl-1,4-beta-D-glucosyl-pyridylaminoside
show the reaction diagram
-
recombinant enzyme
-
-
?
CMP-N-acetylneuraminate + pyridylaminyl-lacto-N-neotetraose
CMP + ?
show the reaction diagram
-
100% activity
-
-
?
CMP-N-acetylneuraminate + submaxillary asialo-mucin
CMP + submaxillary mucin
show the reaction diagram
CMP-N-acetylneuraminate + tumor necrosis factor receptor 1
CMP + alpha2,6-sialyated tumor necrosis factor receptor 1
show the reaction diagram
CMP-N-alpha-neuraminate + ganglioside nLc4Cer
?
show the reaction diagram
-
-
-
-
?
CMP-N-alpha-neuraminate + ganglioside nLc6Cer
?
show the reaction diagram
-
-
-
-
?
CMP-N-alpha-neuraminate + pyridylaminated ganglioside nLc4Cer
?
show the reaction diagram
-
-
-
-
?
CMP-N-aminoacetylneuraminate + asialo-alpha1-acid glycoprotein
?
show the reaction diagram
CMP-N-formylneuraminate + asialo-alpha1-acid glycoprotein
?
show the reaction diagram
CMP-N-glycolylneuraminate + asialo-alpha1-acid glycoprotein
?
show the reaction diagram
CMP-Neu5Ac + lactose
CMP + Neu5Acalpha(2-6)Lac
show the reaction diagram
CMP-Neu5Ac + methyl-beta-D-galactopyranoside
CMP + Neu5Acalpha(2-6)Gal-alpha-methyl
show the reaction diagram
CMP-Neu5Ac + N-acetyllactosamine
CMP + Neu5Acalpha(2-6)LacNAc
show the reaction diagram
cytidine 5'-monophosphate 3-(axial)-fluoro-N-acetylneuraminic acid + alpha-lactose
?
show the reaction diagram
-
[15N]Phe-labeled ST6Gal-I with a 15fold excess of CMP-3FNeuAc
-
-
?
cytidine 5'-monophosphate 4-O-(4-carboxy-2,2,6,6-tetramethylpiperidine-1-oxyl) + alpha-N-acetyllactosamine
?
show the reaction diagram
-
-
-
-
?
cytidine-5'-monophospho-sialic acid + lactose
?
show the reaction diagram
-
-
-
-
?
cytidine-5'-monophospho-sialic acid + N-acetyllactosamine
?
show the reaction diagram
-
-
-
-
?
Galbeta(1,4)GlcNAc-octyl + CMP-Neu5Ac
?
show the reaction diagram
membrane-bound and soluble protein, 100% relative activity
-
-
?
GalNAcbeta(1,4)GlcNAc-octyl + CMP-Neu5Ac
?
show the reaction diagram
membrane-bound and soluble protein, 312% and 346% relative activity, respectively
-
-
?
N-acetyllactosamine 4-O-(4-carboxy-2,2,6,6-tetramethylpiperidine-1-oxyl)
?
show the reaction diagram
-
[15N]Phe-labeled ST6Gal-I with a 20fold excess of N-acetyllactosamine 4-O-(4-carboxy-2,2,6,6-tetramethylpiperidine-1-oxyl)
-
-
?
Neu5Acalpha-4-nitrophenyl + 4-methylumbelliferyl-beta-D-lactoside
?
show the reaction diagram
-
alpha2,6-trans-sialidase activity of DELTA15Pd2,6ST
-
-
?
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->4)-N-acetyl-beta-D-glucosamine
CMP + alpha-N-acetylneuraminyl-(2->6)-beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosamine
show the reaction diagram
CMP-N-acetylneuraminate + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine
CMP + alpha-N-acetylneuraminyl-2,6-beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine
show the reaction diagram
-
-
-
-
?
CMP-N-acetylneuraminate + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosaminyl-R
CMP + alpha-N-acetylneuraminyl-2,6-beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosaminyl-R
show the reaction diagram
CMP-N-acetylneuraminate + tumor necrosis factor receptor 1
CMP + alpha2,6-sialyated tumor necrosis factor receptor 1
show the reaction diagram
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mg2+
about 120% activity in the presence of 10 mM Mg2+
NaCl
-
alpha2,6-sialyltransferase activity is increased approximately 40% in the presence of 300-800 mM
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
Aflatoxins
-
aflatoxins B1, B2a, G1, slightly by aflatoxins B2 and G2, inhibition is probably due to membrane disruption through binding of the aflatoxins and change in enzyme conformation
Alkaline phosphatase
-
CMP-4-O-[2,2,6,6-tetramethylpiperidine-1-oxyl]
-
-
CMP-4-O-[4-carboxy-2,2,6,6-tetramethylpiperidinine-1-oxyl]
-
-
cycloheximide
-
reduces the enzyme expression 3fold in normal hepatocytes and 16 to 17fold in Zaidela ascitic hepatoma, but not in cells isolated from the tumor and cultured for 48 h
cytidine
deoxycholate
-
9fold stimulation at 0.25%, inactivation at 0.5%
endo F
-
inactivation due to deglycosylation of the enzyme, best in methanol or ethanol, less efficient than glycanase
-
Endogenous acidic peptide
-
heat-stable, amino acid composition
-
glycanase
-
inactivation due to deglycosylation of the enzyme, best in methanol or ethanol
-
long chain fatty acids
-
oleic acid, stearic acid, less efficient: palmitic acid, lauric acid, capric acid, caprylic acid or caproic acid, no inhibition by linoleic acid or linolenic acid
N-acetyllactosamine
-
with asialo-alpha1 acid glycoprotein as substrate
PCMB
-
weak
UTP
-
0.25 mM, inhibition decreases at higher concentrations
additional information
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
CMP-N-acetylneuraminate
deoxycholate
-
9fold stimulation at 0.25%, inhibition at 0.5%
natural factor from rat colon
-
may also be present in rat brain and kidney; partially purified; specific, 4fold stimulation by decreasing the Km value for the substrates and increasing Vmax, present in the cytosol, temperature dependent, protease sensitive, independent of metal ions or detergent, unaffceted by monosaccharides; stimulation is decreased by CTP, no activation at 0.75 mM CTP
-
Triton CF-54/Tween 80
-
Triton X-100
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.1
(2S,3S,4R,5R,6R)-5-Acetylamino-4-hydroxy-6-methoxy-3-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
-
-
2.4
(2S,3S,4R,5R,6R)-5-Acetylamino-4-hydroxy-6-methoxy-3-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid methylamide
-
-
11.2
(Gal-3-O-Me)beta(1-3)(GlcNAc-6-O-Me)beta-O-Me
4.1
(Gal-3-O-Me)beta(1-3)GlcNAcbeta-O-Me
-
-
0.6 - 0.8
4-methylumbelliferyl beta-D-lactoside
2.8
5-(5-dimethylaminonaphthalene-1-sulfonyl-2-(2-aminoethoxy))ethyl beta-lactose
-
-
0.92
5-(5-dimethylaminonaphthalene-1-sulfonyl-2-(2-aminoethoxy))ethyl beta-N-acetyllactosamine
-
-
0.0047 - 0.0361
AA-labeled G2 glycan
-
0.14 - 0.53
asialo-alpha1-acid glycoprotein
-
0.078
asialo-ceruloplasmin
-
expressed as concentration of acceptor sites
-
0.0064 - 0.035
asialo-fetuin
-
0.59
asialo-thyroglobulin glycopeptides
-
-
-
0.16 - 0.21
asialo-transferrin
-
1 - 6.5
beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosamine
1.25
beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine
-
-
0.051 - 0.11
CMP-9''-benzamido-Neu5Ac
0.05 - 0.34
CMP-9''-phenylacetamido-Neu5Ac
0.098 - 0.53
CMP-9''-phenylhexanamido-Neu5Ac
0.11 - 0.165
CMP-9''-phenylpropionamido-Neu5Ac
0.12
CMP-9-acetamido-N-acetylneuraminate
-
-
0.72
CMP-9-amino-N-acetylneuraminate
-
-
0.03
CMP-9-benzamido-N-acetylneuraminate
-
-
0.003 - 10.7
CMP-N-acetylneuraminate
0.3
CMP-Neu5Ac
-
alpha2,6-sialyltransferase activity of the truncated recombinant enzyme
0.12 - 0.14
cytidine-5'-monophospho-sialic acid
3.3
Formic acid (2R,3R,4S,5R,6R)-2-((2R,3R,4R,5R,6R)-3-acetylamino-5-hydroxy-2-methoxy-6-methylaminomethyl-tetrahydro-pyran-4-yloxy)-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl ester
-
pH 6.5, 37C
13.6
fucosyl-alpha-1,2-D-galactosyl-beta-1,4-D-glucose
-
-
35.7 - 52.8
Galbeta(1,4)-GlcNAcbeta-4-nitrophenyl
-
2.04 - 2.12
Galbeta(1,4)GlcNAc-octyl
4.3
Galbeta(1-3)(GlcNAc-6-O-Me)beta-O-Me
-
-
1.7
Galbeta(1-3)GlcNAcbeta-O-Me
1.4
Galbeta(1-4)GlcNAc
-
non-reducing terminus of asialofetuin glycans
0.97 - 1.09
GalNAcbeta(1,4)GlcNAc-octyl
1.67
lacto-N-neotetraose
-
-
1.8 - 129
lactose
0.7
Methanesulfonic acid (2R,3S,4R,5R,6R)-5-acetylamino-4-hydroxy-6-methoxy-3-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester
-
-
99 - 174
methyl-beta-D-galactopyranoside
11.6
N-((1R,3R,5R,6R,7S,8R,13R,15R,16R,17S)-6,7,17-Trihydroxy-5-hydroxymethyl-15-methoxy-2,4,9,11,14-pentaoxa-tricyclo[11.3.1.03,8]heptadec-16-yl)-acetamide
-
pH 6.5, 37C
1
N-((1R,3R,5R,6R,7S,8R,14R,16R,17R,18R)-6,7,18-trihydroxy-5-hydroxymethyl-16-methoxy-11-oxo-2,4,9,15-tetraoxa-12-aza-tricyclo[12.3.1.03,8]octadec-17-yl)-acetamide
-
pH 6.5, 37C
1.1
N-((1R,3R,5R,6R,7S,8R,14R,16R,17R,18S)-6,7,18-Trihydroxy-5-hydroxymethyl-16-methoxy-2,4,9,12,15-pentaoxa-tricyclo[12.3.1.03,8]octadec-17-yl)-acetamide
-
pH 6.5, 37C
1.62 - 15.4
N-acetyllactosamine
8.95
N-acetyllactosaminide
-
-
0.8
N-[(2R,3R,4R,5S,6R)-4-Hydroxy-6-(methanesulfonylamino-methyl)-2-methoxy-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
-
-
3.1
N-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-3-methoxy-tetrahydro-pyran-2-yloxy)-6-formylaminomethyl-4-hydroxy-2-methoxy-tetrahydro-pyran-3-yl]-acetamide
-
-
1.4
N-[(2R,3R,4R,5S,6R)-6-(Acetylamino-methyl)-4-hydroxy-2-methoxy-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
-
-
5.8
N-[(2R,3R,4R,5S,6R)-6-Aminomethyl-4-hydroxy-2-methoxy-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
-
-
8.1
Neu5Acalpha-2,3-Galbeta-1,4-Glc
-
-
53
Neu5Acalpha-4-nitrophenyl
-
alpha2,6-trans-sialidase activity of DELTA15Pd2,6ST
0.91
nLc4Cer
-
recombinant enzyme
3.5
pyridylamine-type 2H
-
recombinant enzyme, in 50 mM MES-NaOH buffer (pH 6.0), 1 mM MnCl2, at 37C
102
pyridylamino-lactose
-
recombinant enzyme
1.3
pyridylamino-N-acetyllactosamine
-
recombinant enzyme
1.5
pyridylamino-nLc4Cer
-
recombinant enzyme
0.9
pyridylaminyl-lacto-N-neotetraose
-
recombinant enzyme, in 50 mM MES-NaOH buffer (pH 6.0), 1 mM MnCl2, at 37C
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.1 - 2.3
4-methylumbelliferyl beta-D-lactoside
0.087
5-(5-dimethylaminonaphthalene-1-sulfonyl-2-(2-aminoethoxy))ethyl beta-lactose
Rattus norvegicus
-
-
1.13
5-(5-dimethylaminonaphthalene-1-sulfonyl-2-(2-aminoethoxy))ethyl beta-N-acetyllactosamine
Rattus norvegicus
-
-
0.07 - 0.67
beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosamine
0.05 - 20.3
CMP-N-acetylneuraminate
4.3 - 110
lactose
0.883
Neu5Acalpha-4-nitrophenyl
Photobacterium damselae
-
alpha2,6-trans-sialidase activity of DELTA15Pd2,6ST
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.031
5-(5-dimethylaminonaphthalene-1-sulfonyl-2-(2-aminoethoxy))ethyl beta-lactose
Rattus norvegicus
-
-
40078
1.23
5-(5-dimethylaminonaphthalene-1-sulfonyl-2-(2-aminoethoxy))ethyl beta-N-acetyllactosamine
Rattus norvegicus
-
-
40077
0.01 - 0.44
beta-D-galactosyl-(1->4)-N-acetyl-beta-D-glucosamine
193433
0.13 - 7.3
CMP-N-acetylneuraminate
180
0.58 - 1.78
lactose
114
0.016
Neu5Acalpha-4-nitrophenyl
Photobacterium damselae
-
alpha2,6-trans-sialidase activity of DELTA15Pd2,6ST
40079
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0047 - 0.016
CDP
0.18
CMP
-
-
4.07
CMP-4-O-[2,2,6,6-tetramethylpiperidine-1-oxyl]
-
pH 6.5, 37C
0.79
CMP-4-O-[4-carboxy-2,2,6,6-tetramethylpiperidinine-1-oxyl]
-
pH 6.5, 37C
additional information
additional information
-
-
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
8.7
CMP-4-O-[2,2,6,6-tetramethylpiperidine-1-oxyl]
Rattus norvegicus
-
pH 6.5, 37C
1.7
CMP-4-O-[4-carboxy-2,2,6,6-tetramethylpiperidinine-1-oxyl]
Rattus norvegicus
-
pH 6.5, 37C