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Merck
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A7229

Sigma-Aldrich

PUGNAc

≥95% (HPLC)

别名:

O-(2-乙酰氨基-2-脱氧-D-吡喃葡萄糖亚基氨基)-N-苯基氨基甲酸酯

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About This Item

经验公式（希尔记法）:
C15H19N3O7
CAS号:
132489-69-1
分子量:
353.33
Beilstein:
4274031
MDL编号:
MFCD00145022
UNSPSC代码:
12352204
PubChem化学物质编号:
329770921
NACRES:
NA.26
价格与库存信息目前不能提供

方案

≥95% (HPLC)

表单

crystals

储存温度

−20°C

SMILES字符串

CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O\C1=N/OC(=O)Nc2ccccc2

InChI

1S/C15H19N3O7/c1-8(20)16-11-13(22)12(21)10(7-19)24-14(11)18-25-15(23)17-9-5-3-2-4-6-9/h2-6,10-13,19,21-22H,7H2,1H3,(H,16,20)(H,17,23)/b18-14-/t10-,11-,12-,13-/m1/s1

InChI key

PBLNJFVQMUMOJY-JXZOILRNSA-N

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相关类别

应用

O-(2-乙酰氨基-2-脱氧-D-吡喃葡萄糖亚基)氨基-N-苯基氨基甲酸酯(PUGNAc)已用于评估水飞蓟宾(silibinin)对成人视网膜色素上皮19(ARPE-19)细胞中的糖蛋白O-GlcNAc水平的影响。[1]它还用作大鼠大脑样品用HEPES裂解缓冲液的组分。[2]
PUGNAc用作O-GlcNAc-β-N-乙酰葡糖胺糖苷酶的抑制剂。[3][4][5]

生化/生理作用

O-(2-乙酰氨基-2-脱氧-D-吡喃葡萄糖亚基)氨基-N-苯基氨基甲酸酯(PUGNAc)通过降低胰岛素诱导的蛋白激酶B(Akt)和糖原合成酶激酶3β(GSK3β)的磷酸化，诱发3T3-L1脂肪细胞的胰岛素抵抗。[6]
PUGNAc是肽O-GlcNAc-β-N-乙酰葡糖胺糖苷酶的体外和体内抑制剂，该酶从O-连接的糖基化蛋白中除去O-连接的N-乙酰葡糖胺（O-GlcNAc）。

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Gloves, type N95 (US)

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
BCCM8141
BCCJ9105
BCCL1405
BCCG7338
BCCF9057

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O-GlcNAc modification on IRS-1 and Akt2 by PUGNAc inhibits their phosphorylation and induces insulin resistance in rat primary adipocytes
Park S Y, et al.
Experimental & Molecular Medicine, 37(3), 220-220 (2005)
Ching-Wen Ho et al.
ACS chemical biology, 5(5), 489-497 (2010-03-02)
Human N-acetyl-beta-hexosaminidase (Hex) isozymes are considered to be important targets for drug discovery. They are directly linked to osteoarthritis because Hex is the predominant glycosidase released by chondrocytes to degrade glycosaminoglycan. Hex is also associated with lysosomal storage disorders. We
Matthew S Macauley et al.
Biochimica et biophysica acta, 1800(2), 107-121 (2009-08-12)
The O-GlcNAc modification is found on many nucleocytoplasmic proteins. The dynamic nature of O-GlcNAc, which in some ways is reminiscent of phosphorylation, has enabled investigators to modulate the stoichiometry of O-GlcNAc on proteins in order to study its function. Although
Helge C Dorfmueller et al.
The Biochemical journal, 420(2), 221-227 (2009-03-12)
O-GlcNAcylation is an essential, dynamic and inducible post-translational glycosylation of cytosolic proteins in metazoa and can show interplay with protein phosphorylation. Inhibition of OGA (O-GlcNAcase), the enzyme that removes O-GlcNAc from O-GlcNAcylated proteins, is a useful strategy to probe the
Silibinin inhibits ICAM-1 expression via regulation of N-linked and O-linked glycosylation in ARPE-19 cells
Chen Y H, et al.
BioMed Research International, 2014 (2014)
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