A7229
PUGNAc
≥95% (HPLC)
Synonym(s):
O-(2-Acetamido-2-deoxy-D-glucopyranosylidenamino) N-phenylcarbamate
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About This Item
Empirical Formula (Hill Notation):
C15H19N3O7
CAS Number:
Molecular Weight:
353.33
UNSPSC Code:
12352204
NACRES:
NA.26
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
4274031
Assay:
≥95% (HPLC)
Form:
crystals
Quality Level
assay
≥95% (HPLC)
form
crystals
storage temp.
−20°C
SMILES string
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
Related Categories
Application
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.
Biochem/physiol Actions
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.
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).
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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
GlcNAcstatins are nanomolar inhibitors of human O-GlcNAcase inducing cellular hyper-O-GlcNAcylation.
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.
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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