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Merck
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Documenti

A7229

Sigma-Aldrich

PUGNAc

≥95% (HPLC)

Sinonimo/i:

O-(2-Acetamido-2-deoxy-D-glucopyranosylidenamino) N-phenylcarbamate

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About This Item

Formula empirica (notazione di Hill):
C15H19N3O7
Numero CAS:
132489-69-1
Peso molecolare:
353.33
Beilstein:
4274031
Numero MDL:
MFCD00145022
Codice UNSPSC:
12352204
ID PubChem:
329770921
NACRES:
NA.26

Saggio

≥95% (HPLC)

Forma fisica

crystals

Temperatura di conservazione

−20°C

Stringa SMILE

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
PBLNJFVQMUMOJY-JXZOILRNSA-N

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Applicazioni

O-(2-acetamido-2deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate (PUGNAc) has been used to evaluate the effects of silibinin on O-GlcNAc levels of glycoproteins in Adult Retinal Pigment Epithelial-19 (ARPE-19) cells. It has also been used as a component of the HEPES lysis buffer for rat brain samples.
PUGNAc has been used as an inhibitor of O-GlcNAc-β-N-acetylglucosaminidase.

Azioni biochim/fisiol

O-(2-acetamido-2deoxy-D-glucopyranosylidene)amino-N-phenylcarbamate (PUGNAc) induces insulin resistance in 3T3-L1 adipocytes by reducing insulin-prompting phosphorylation of protein kinase B (Akt) and glycogen synthase kinase 3β (GSK3β).
PUGNAc is an in vitro and in vivo inhibitor of peptide O-GlcNAc-β-N-acetylglucosaminidase, the enzyme which removes O-linked N-acetylglucosamine (O-GlcNAc) from O-linked glycosylated proteins.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

Certificati d'analisi (COA)

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N-acetil-D-glucosammina ≥99% (HPLC)

Sigma-Aldrich

A8625

N-acetil-D-glucosammina

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Sigma-Aldrich

A3286

N-acetil-D-glucosammina

6-Diazo-5-oxo-L-norleucine crystalline

Sigma-Aldrich

D2141

6-Diazo-5-oxo-L-norleucine

1S,3R-RSL 3 ≥98% (HPLC)

Sigma-Aldrich

SML2234

1S,3R-RSL 3

Erastin ≥98% (HPLC)

Sigma-Aldrich

E7781

Erastin

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)
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
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
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
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