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Merck
CN

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
Beilstein:
4274031
MDL number:
MFCD00145022
UNSPSC Code:
12352204
PubChem Substance ID:
329770921
NACRES:
NA.26

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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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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
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
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