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Merck

A7229

PUGNAc

≥95% (HPLC)

Synonym(s):

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

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5 MG

CZK 5,050.00

10 MG

CZK 9,420.00

CZK 5,050.00

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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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Quality Level

100

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

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This Item
N8759T2144A3007
PUGNAc ≥95% (HPLC)

Sigma-Aldrich

A7229

PUGNAc

4-Nitrophenyl N-acetyl-α-D-glucosaminide ≥98%

Sigma-Aldrich

N8759

4-Nitrophenyl N-acetyl-α-D-glucosaminide

N,N′,N′′-Triacetylchitotriose ≥93% (HPLC)

Sigma-Aldrich

T2144

N,N′,N′′-Triacetylchitotriose

N-Acetylmuramic acid ≥98% (TLC)

Sigma-Aldrich

A3007

N-Acetylmuramic acid

assay

≥95% (HPLC)

assay

≥98%

assay

≥93% (HPLC)

assay

≥98% (TLC)

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

200

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

form

crystals

form

powder

form

powder

form

powder

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.[1]

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCP4215
BCCM8141
BCCJ9105
BCCL1405
BCCG7338

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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
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
View All Related Papers

Global Trade Item Number

SKUGTIN
A7229-10MG04061833383841
A7229-5MG04061833383858

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