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Merck
CN

B4894

苄基2-乙酰氨基-2-脱氧-α-D-半乳糖苷

O-glycosylation inhibitor, ≥97% (TLC)

别名:

苄基-α-乙酰半乳糖胺, α-D-GalNAc-1→OCH2Ph, 乙酰半乳糖胺α-O-苄基, 乙酰半乳糖胺-O-bn, 苄基N-乙酰基-α-D-半乳糖胺

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关于此项目

经验公式(希尔记法):
C15H21NO6 · xH2O
化学文摘社编号:
分子量:
311.33 (anhydrous basis)
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
12352201
MDL number:
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产品名称

苄基2-乙酰氨基-2-脱氧-α-D-半乳糖苷, O-glycosylation inhibitor, ≥97% (TLC)

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

SMILES string

CC(N[C@H]([C@H]([C@H]1O)O)[C@H](O[C@@H]1CO)OCC2=CC=CC=C2)=O

InChI key

SKOZFDIGKDPQBO-QMIVOQANSA-N

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

Quality Level

Biochem/physiol Actions

苄基-N-乙酰基-α- 氨基半乳糖苷抑制糖基转移酶将葡萄糖胺掺入O-聚糖中。 抑制乳腺癌细胞系MDF-7中粘蛋白的生物合成并抑制MUC1的表达。

Other Notes

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存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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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
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
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.
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
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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