B4894
Benzyl 2-acetamido-2-deoxy-α-D-galactopyranoside
O-glycosylation inhibitor, ≥97% (TLC)
Synonym(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
Empirical Formula (Hill Notation):
C15H21NO6 · xH2O
CAS Number:
Molecular Weight:
311.33 (anhydrous basis)
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
12352201
MDL number:
Quality Level
assay
≥97% (TLC)
form
powder
color
white to off-white
mp
204-208 °C
solubility
methanol: soluble 10 mg/mL, clear
storage temp.
−20°C
SMILES string
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
InChI key
SKOZFDIGKDPQBO-QMIVOQANSA-N
Biochem/physiol Actions
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.
Other Notes
To gain a comprehensive understanding of our extensive range of Disaccharides for your research, we encourage you to visit our Carbohydrates Category page.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Robert C De Lisle
Journal of cell science, 115(Pt 14), 2941-2952 (2002-06-26)
Packaging of proteins into regulated secretory granules is mediated by the mildly acidic pH of the trans Golgi network and immature secretory granules. This need for an acidic pH indicates that ionic interactions are important. The mouse pancreatic acinar cell
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
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| B4894-25MG | 04061833433522 |
| B4894-100MG | 04061832960791 |
| B4894-500MG | 04061832960807 |