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B4894

Sigma-Aldrich

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

O-glycosylation inhibitor, ≥97% (TLC)

Sinônimo(s):

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 (Notação de Hill):
C15H21NO6 · xH2O
Número CAS:
3554-93-6
Peso molecular:
311.33 (anhydrous basis)
Número MDL:
MFCD00057920
Código UNSPSC:
12352201
ID de substância PubChem:
24891802
NACRES:
NA.25

Ensaio

≥97% (TLC)

forma

powder

cor

white to off-white

pf

204-208  °C

solubilidade

methanol: soluble 10 mg/mL, clear

temperatura de armazenamento

−20°C

cadeia de caracteres 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

chave InChI

SKOZFDIGKDPQBO-QMIVOQANSA-N

Categorias relacionadas

Ações bioquímicas/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.

Outras 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 classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)

Certificados de análise (COA)

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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
Gabi Wetzel et al.
Biological chemistry, 390(7), 545-549 (2009-05-12)
Sucrase-isomaltase (SI) is a highly N- and O-glycosylated intestinal brush border membrane protein. SI is sorted with high fidelity to the apical membrane via O-linked glycans that mediate its association with lipid rafts or detergent-resistant membranes (DRMs). Here, we show
Koji Kimura et al.
Animal reproduction science, 103(3-4), 228-238 (2007-01-03)
Glucosamine is a component of hyaluronic acid and an alternative substrate to glucose for the extracellular matrix synthesis of COCs. Its addition to an IVM medium reduces the glucose consumption of bovine COCs. Glucosamine is also metabolized to UDP-N-acetyl glucosamine
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
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