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Merck

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
分子量:
353.33
Beilstein:
4274031
MDL號碼:
分類程式碼代碼:
12352204
PubChem物質ID:
NACRES:
NA.26

化驗

≥95% (HPLC)

形狀

crystals

儲存溫度

−20°C

SMILES 字串

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 密鑰

PBLNJFVQMUMOJY-JXZOILRNSA-N

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相关类别

應用

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。它还用作大鼠大脑样品用HEPES裂解缓冲液的组分。
PUGNAc用作O-GlcNAc-β-N-乙酰葡糖胺糖苷酶的抑制剂。

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。
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)。

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable

個人防護裝備

Eyeshields, Gloves, type N95 (US)


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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)
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
Roselle Gélinas et al.
Nature communications, 9(1), 374-374 (2018-01-27)
AMP-activated protein kinase (AMPK) has been shown to inhibit cardiac hypertrophy. Here, we show that submaximal AMPK activation blocks cardiomyocyte hypertrophy without affecting downstream targets previously suggested to be involved, such as p70 ribosomal S6 protein kinase, calcineurin/nuclear factor of
Tet proteins connect the O-linked N-acetylglucosamine transferase Ogt to chromatin in embryonic stem cells.
Vella P, et al.
Molecular Cell, 49, 645-656 (2013)
Matthew S Macauley et al.
Chemistry & biology, 17(9), 937-948 (2010-09-21)
To probe increased O-GlcNAc levels as an independent mechanism governing insulin resistance in 3T3-L1 adipocytes, a new class of O-GlcNAcase (OGA) inhibitor was studied. 6-Acetamido-6-deoxy-castanospermine (6-Ac-Cas) is a potent inhibitor of OGA. The structure of 6-Ac-Cas bound in the active

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