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Merck

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:
132489-69-1
Molecular Weight:
353.33
UNSPSC Code:
12352204
NACRES:
NA.26
PubChem Substance ID:
329770921
MDL number:
MFCD00145022
Beilstein/REAXYS Number:
4274031
Assay:
≥95% (HPLC)
Form:
crystals

Key Documents

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SMILES string

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

InChI key

PBLNJFVQMUMOJY-JXZOILRNSA-N

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

assay

≥95% (HPLC)

form

crystals

storage temp.

−20°C

Quality Level

100

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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

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.

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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Certificates of Analysis (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
Shunichi Yokoe et al.
Glycobiology, 20(10), 1217-1226 (2010-05-21)
Cardiac-type sarco(endo)plasmic reticulum Ca(2)-ATPase (SERCA2a) plays a major role in cardiac muscle contractility. Phospholamban (PLN) regulates the function of SERCA2a via its Ser(16)-phosphorylation. Since it has been proposed that the Ser/Thr residues on cytoplasmic and nuclear proteins are modified by
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
O-GlcNAc modification is associated with insulin sensitivity in the whole blood of healthy young adult males.
Myslicki JP, et al.
Diabetology & Metabolic Syndrome, 6, 96-96 (2014)
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