Information on EC 2.4.99.7 - alpha-N-acetylneuraminyl-2,3-beta-galactosyl-1,3-N-acetylgalactosaminide 6-alpha-sialyltransferase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
2.4.99.7
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RECOMMENDED NAME
GeneOntology No.
alpha-N-acetylneuraminyl-2,3-beta-galactosyl-1,3-N-acetylgalactosaminide 6-alpha-sialyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
CMP-N-acetylneuraminate + N-acetyl-alpha-neuraminyl-(2->3)-beta-D-galactosyl-(1->3)-N-acetyl-D-galactosaminyl-R = CMP + N-acetyl-alpha-neuraminyl-(2->3)-beta-D-galactosyl-(1->3)-[N-acetyl-alpha-neuraminyl-(2->6)]-N-acetyl-D-galactosaminyl-R
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
Glycosphingolipid biosynthesis - ganglio series
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Metabolic pathways
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SYSTEMATIC NAME
IUBMB Comments
CMP-N-acetylneuraminate:N-acetyl-alpha-neuraminyl-(2->3)-beta-D-galactosyl-(1->3)- N-acetyl-D-galactosaminide galactosamine-6-alpha-N-acetylneuraminyltransferase
Attaches N-acetylneuraminic acid in alpha-2,6-linkage to N-acetyl-galactosamine only when present in the structure of alpha-N-acetyl-neuraminyl-(2->3)-beta-galactosyl-(1->3)-N-acetylgalactosaminyl-R, where R may be protein or p-nitrophenol. Not identical with EC 2.4.99.3 alpha-N-acetylgalactosaminide alpha-2,6-sialyltransferase.
CAS REGISTRY NUMBER
COMMENTARY hide
129924-24-9
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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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Manually annotated by BRENDA team
sheep
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Manually annotated by BRENDA team
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 + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,3-N-acetyl-D-galactosaminyl-R
CMP + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,3-(N-acetylneuraminyl-2,6)-N-acetyl-D-galactosaminyl-R
show the reaction diagram
CMP-N-acetylneuraminate + alpha1-acid glycoprotein
?
show the reaction diagram
acceptor structur: Neu5Acalpha2-6Galbeta1-4GlcNac-R, 8.7% of activity with fetuin
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?
CMP-N-acetylneuraminate + fetuin
?
show the reaction diagram
acceptor structures: Neu5Acalpha2-3Galbeta1-3GalNacalpha1-O-Ser/Thr, Neu5Acalpha2-3Galbeta1-3[Neu5Acalpha2-6]GalNacalpha1-O-Ser/Thr and Neu5Acalpha2-6(3)Galbeta1-4GlcNac-R
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?
CMP-N-acetylneuraminate + GlcNac-alpha1-O-benzyl
?
show the reaction diagram
7.6% of activity with fetuin
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?
CMP-N-acetylneuraminate + GM1b
CMP + ?
show the reaction diagram
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?
CMP-N-acetylneuraminate + monosialylgalactosylgloboside
CMP + disialylgalactosylgloboside
show the reaction diagram
isoforms ST6GalNAc III and ST6GalNAc VI generate disialylgalactosylgloboside from monosialylgalactosylgloboside with Vmax/Km values of 1.91 and 4.16 respectively
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?
CMP-N-acetylneuraminate + N-alpha-acetylneuraminyl-2,3-beta-D-galactosyl-1,3-N-acetyl-D-galactosaminyl-R
CMP + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,3-(N-acetylneuraminyl-2,6)-N-acetyl-D-galactosaminyl-R
show the reaction diagram
CMP-N-acetylneuraminate + Neu5Acalpha2-3Galbeta1-3GalNac
?
show the reaction diagram
60.3% of activity with fetuin
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?
CMP-N-acetylneuraminate + Neu5Acalpha2-3Galbeta1-4GlcNac-alpha1-O-benzyl
?
show the reaction diagram
224% of activity with fetuin
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?
CMP-N-acetylneuraminate + NeuAc-alpha-(2->3)-Gal-beta-(1->3)-GalNAc
?
show the reaction diagram
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?
CMP-N-acetylneuraminate + sialyl lactoetraosylceramide
CMP + ?
show the reaction diagram
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product are disialyl Lewis a structures
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?
CMP-NAC + monosialylgalactosylgloboside
CMP + disialylgalactosylgloboside
show the reaction diagram
CMP-Neu5Ac + fetuin
?
show the reaction diagram
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ST6GalNAc III also shows activity with O-glycans, but not N-glycans, in fetuin
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?
CMP-Neu5Ac + Galbeta1,3GlcNAcbeta1,3Galbeta1,4Glcbeta1-Cer
?
show the reaction diagram
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?
CMP-Neu5Ac + Galbeta1,4GlcNAcbeta1,3Galbeta1,4Glcbeta1-Cer
?
show the reaction diagram
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CMP-Neu5Ac + GM1b
?
show the reaction diagram
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i.e. NeuAcalpha2,3Galbeta1,3GalNAcbeta1,4Galbeta1,4Glcbeta1-Cer, best substrate
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?
CMP-NeuAc + glycoprotein
?
show the reaction diagram
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?
CMP-NeuAc + glycosphingolipid
?
show the reaction diagram
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?
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 + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,3-N-acetyl-D-galactosaminyl-R
CMP + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,3-(N-acetylneuraminyl-2,6)-N-acetyl-D-galactosaminyl-R
show the reaction diagram
CMP-N-acetylneuraminate + NeuAc-alpha-(2->3)-Gal-beta-(1->3)-GalNAc
?
show the reaction diagram
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?
CMP-NAC + monosialylgalactosylgloboside
CMP + disialylgalactosylgloboside
show the reaction diagram
Q8NDV1, Q969X2
the enzyme is responsible for the synthesis of disialylgalactosylgloboside from monosialylgalactosylgloboside in normal and malignant kidney cells, the reaction suppressed during the malignant transformation of the proximal tubules as a maturation arrest of glycosylation, overview
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?
additional information
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enzyme is responsible for synthesis of disialyl Lewis a structures in colon tissues, but not for synthesis of alpha-series gangliosides, model of pathway for synthesis of disialyl lactoetraosylceramides and disialyl Lewis a structures
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
5,5'-dithiobis-(2-nitrobenzoic acid)
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0.01 mM, 50% inhibition, 0.1 mM, 97% inhibition
6,6'-dithiodinicotinic acid carboxypyridine disulfide
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IC50: 0.028 mM
CMP
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50 mM, strong inhibition
Mersalyl acid
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0.025 mM, 50% inhibition
N-bromosuccinimide
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5 mM, 98% inhibition
N-ethylmaleimide
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0.014 mM, 50% non-competitive inhibition, almost complete protection with 0.05 mM CMP-N-acetylneuraminate
p-chloromercuribenzoic acid
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0.036 mM, 50% inhibition, 0.1 mM, 97% inhibition
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.07
CMP-N-acetylneuraminate
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0.33 - 0.56
GM1b
1.1
Neu5Acalpha2-3Galbeta1-3GalNac
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2.21
Neu5Acalpha2-3Galbeta1-3GalNacalpha-O-benzyl
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0.46 - 0.9
sialyl lactoetraosylceramide
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.028
6,6'-dithiodinicotinic acid carboxypyridine disulfide
Rattus norvegicus
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IC50: 0.028 mM
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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Epstein-Barr virus transformed cell line
Manually annotated by BRENDA team
expression of ST6GalNAc VI
Manually annotated by BRENDA team
; renal cancer cell line, expression of ST6GalNAc VI
Manually annotated by BRENDA team
expression of ST6GalNAc VI
Manually annotated by BRENDA team
; renal cancer cell line, expression of ST6GalNAc VI
Manually annotated by BRENDA team
; renal cancer cell line, expression of ST6GalNAc VI
Manually annotated by BRENDA team
; renal cancer cell line, expression of ST6GalNAc VI
Manually annotated by BRENDA team
; renal cancer cell line, expression of ST6GalNAc VI
Manually annotated by BRENDA team
; renal cancer cell line, expression of ST6GalNAc VI
Manually annotated by BRENDA team
; renal cancer cell line, expression of ST6GalNAc VI
Manually annotated by BRENDA team
renal cancer cell line, expression of ST6GalNAc VI
Manually annotated by BRENDA team
; renal cancer cell line, expression of ST6GalNAc VI
Manually annotated by BRENDA team
; renal cancer cell line, expression of ST6GalNAc VI
Manually annotated by BRENDA team
; renal cancer cell line, expression of ST6GalNAc VI
Manually annotated by BRENDA team
constitutive expression of ST6GalNac IV gene
Manually annotated by BRENDA team
expression of ST6GalNAc VI
Manually annotated by BRENDA team
expression of ST6GalNAc VI
Manually annotated by BRENDA team
constitutive expression of ST6GalNac IV gene
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
34900
x * 34900, deduced from nucleotide sequence
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 34900, deduced from nucleotide sequence
additional information
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two transmembrane isozymes, short and long enzyme form of 305 and 240 amino acids, respectively, the long form shows a short cytoplasmic transmembrane domain of sixteen amino acids and a catalytic domain of 280 amino acids, both isozymes contain the sialyl motif L and sialyl motif S, overview
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
co-expression of ST6GalNAc VI and ST6GalNAc III with disialylgalactosylgloboside in Caki-1 cells; co-expression of ST6GalNAc VI and ST6GalNAc III with disialylgalactosylgloboside in Caki-1 cells
expression of ST6GalNac IV in COS-7 cells
phylogenetic analysis, sequence comparison and sialylmotif regions analysis, overview; phylogenetic analysis, sequence comparison and sialylmotif regions analysis, overview; phylogenetic analysis, sequence comparison and sialylmotif regions analysis, overview; phylogenetic analysis, sequence comparison and sialylmotif regions analysis, overview
short and long enzyme form of 305 and 240 amino acids, respectively, DNA and amino acid sequence determination and analysis, alternative usage of the second exon seems to generate these two transcripts, expression analysis, sequence comparisons, overview, expression of soluble fusion enzyme, a truncated form of ST6GalNAc III lacking 21 amino acids from the NH2 terminus
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ST6GalNac III and IV genes
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
medicine
the expression profiles of isoform ST6GalNAc VI among 20 renal cancer cell lines correlates clearly with those of disialylgalactosylgloboside, suggesting that the sialyltransferase involved in the synthesis of disialylgalactosylgloboside in the kidney is ST6GalNAc-VI. ST6GalNAc-VI and disialylgalactosylgloboside are found in proximal tubule epithelial cells in normal kidney tissues, while they are downregulated in renal cancer cell lines and cancer tissues