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Key Documents

B4894

Sigma-Aldrich

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

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)
MDL number:
MFCD00057920
UNSPSC Code:
12352201
PubChem Substance ID:
24891802
NACRES:
NA.25

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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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