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B4894

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

Name: Benzyl 2-acetamido-2-deoxy-α-<sc>D</sc>-galactopyranoside
Brand: SIGMA

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:

3554-93-6

Molecular Weight:

311.33 (anhydrous basis)

NACRES:

NA.25

PubChem Substance ID:

24891802

UNSPSC Code:

12352201

MDL number:

MFCD00057920

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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

Related Categories

Biochemicals

Carbohydrates for Biochemical Research

Cell Culture Supplements & Reagents

Chemical Biology

Chemistry & Biochemicals

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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Inhibition of mucin glycosylation by aryl-N-acetyl-alpha-galactosaminides in human colon cancer cells.

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

[Correlation of MUC1 expression to adhesion of breast cancer cell line MDA-MB-231].

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

Inhibition of CD44 N- and O-linked glycosylation decreases endometrial cell lines attachment to peritoneal mesothelial cells.

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

Antiadhesive character of mucin O-glycans at the apical surface of corneal epithelial cells.

Mika Sumiyoshi et al.

Investigative ophthalmology & visual science, 49(1), 197-203 (2008-01-04)

Prolonged contact of opposite mucosal surfaces, which occurs on the ocular surface, oral cavity, reproductive tract, and gut, requires a specialized apical cell surface that prevents adhesion. The purpose of this study was to evaluate the contribution of mucin O-glycans

Inhibition of the O-glycan elongation limits MUC1 incorporation to cell membrane of human endometrial carcinoma cells.

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

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Global Trade Item Number

SKU	GTIN
B4894-25MG	04061833433522
B4894-100MG	04061832960791
B4894-500MG	04061832960807

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