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B4894

Sigma-Aldrich

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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100 MG
$539.00

$539.00

Estimated to ship onJune 15, 2025

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100 MG
$539.00

About This Item

Empirical Formula (Hill Notation):
C15H21NO6 · xH2O
CAS Number:
3554-93-6
Molecular Weight:
311.33 (anhydrous basis)
MDL number:
MFCD00057920
UNSPSC Code:
12352201
PubChem Substance ID:
24891802
NACRES:
NA.25

$539.00

Estimated to ship onJune 15, 2025

Request a Bulk Order

Quality Level

100

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV6065
MKCV0683
MKCQ0048
MKCQ4422
MKCP5690

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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
Allison K Rodgers et al.
Fertility and sterility, 95(2), 823-825 (2010-10-26)
The attachment of endometrial epithelial cells (EECs) and endometrial stromal cells (ESCs) to peritoneal mesothelial cells (PMCs) with and without inhibition of N- and O-linked glycosylation, the viability of EECs and ESCs, and the expression of CD44 surface density were
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
Ashish V Kalra et al.
European journal of cancer (Oxford, England : 1990), 45(1), 164-173 (2008-12-03)
Current treatments for pancreatic cancer have failed to effectively manage the disease, and hence, more effective treatment approaches are urgently needed. Studies suggest that mucin O-glycosylation limits the cytotoxic effect of fluorouracil (5-FU) against the growth of human pancreatic cancer
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