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B4894

Sigma-Aldrich

Benzyl 2-acetamido-2-deoxy-α-D-galactopyranoside

O-glycosylation inhibitor, ≥97% (TLC)

Sinónimos:

Benzyl-α-GalNAc, α-D-GalNAc-1→OCH2Ph, Benzyl N-acetyl-α-D-galactosaminide, GalNAc α-O-benzyl, GalNAc-O-bn

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About This Item

Fórmula empírica (notación de Hill):
C15H21NO6 · xH2O
Número de CAS:
Peso molecular:
311.33 (anhydrous basis)
Número MDL:
Código UNSPSC:
12352201
ID de la sustancia en PubChem:
NACRES:
NA.25
En este momento no podemos mostrarle ni los precios ni la disponibilidad

Nivel de calidad

Ensayo

≥97% (TLC)

Formulario

powder

color

white to off-white

mp

204-208  °C

solubilidad

methanol: soluble 10 mg/mL, clear

temp. de almacenamiento

−20°C

cadena SMILES

CC(N[C@H]([C@H]([C@H]1O)O)[C@H](O[C@@H]1CO)OCC2=CC=CC=C2)=O

InChI

InChI=1S/C15H21NO6/c1-9(18)16-12-14(20)13(19)11(7-17)22-15(12)21-8-10-5-3-2-4-6-10/h2-6,11-15,17,19-20H,7-8H2,1H3,(H,16,18)/t11-,12-,13+,14-,15+/m1/s1

Clave InChI

SKOZFDIGKDPQBO-QMIVOQANSA-N

Acciones bioquímicas o fisiológicas

Benzyl-N-acetyl-α-galactosaminide inhibits glycosyltransferase incorporation of glucosamine into O-glycans. Suppresses mucin biosynthesis and inhibits MUC1 expression in breast cancer cell line MDF-7.

Otras notas

To gain a comprehensive understanding of our extensive range of Disaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)


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S F Kuan et al.
The Journal of biological chemistry, 264(32), 19271-19277 (1989-11-15)
Specific inhibitors of the glycosylation of O-glycosidically linked glycoproteins have not previously been described. When tested for their effects on mucin glycosylation in a mucin-producing colon cancer cell line, LS174T, benzyl-, phenyl-, and p-nitrophenyl-N-acetyl-alpha-galactosaminide inhibited the formation of fully glycosylated
Fausto Ulloa et al.
The Journal of biological chemistry, 278(14), 12374-12383 (2003-01-23)
The sugar analog O-benzyl-N-acetyl-alpha-d-galactosaminide (BG) is an inhibitor of glycan chain elongation and inhibits alpha2,3-sialylation in mucus-secreting HT-29 cells. Long-term exposure of these cells to BG is associated with the accumulation of apical glycoproteins in cytoplasmic vesicles. The mechanisms involved
Li Lu et al.
Ai zheng = Aizheng = Chinese journal of cancer, 23(11), 1294-1296 (2004-11-04)
Recent researches found that an abundant production of mucin protein well correlates with tumor cell metastasis. This study was to investigate inhibitory effect of benzyl-alpha-GalNAc on production of mucin 1 (MUC1), and on adhesion and invasion of breast cancer cell
Halina Porowska et al.
International journal of molecular medicine, 13(3), 459-464 (2004-02-10)
We have studied how benzyl-N-acetyl-alpha-D-galactosaminide, O-glycosylation inhibitor, affects the polymorphism and shedding of membrane-bound MUC1 mucin, and change in adhesive properties of cancer cells. In endometrial adenocarcinoma cells (Ishikawa line), high molecular weight MUC1 mucin was shed from cellular membrane
A V Kalra et al.
British journal of cancer, 97(7), 910-918 (2007-10-04)
Mucins are high molecular weight glycoproteins expressed on the apical surface of normal epithelial cells. In cancer disease mucins are overexpressed on the entire cellular surface. Overexpression of MUC1 mucin in pancreatic tumours has been correlated with poor patient survival.

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