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Key Documents

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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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
Pricing and availability is not currently available.

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW5682
MKCV6065
MKCV0683
MKCQ0048
MKCQ4422

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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
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
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
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
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