PugNAc

Names

[ Name ]:
PugNAc

[Synonym ]:
(Z)-Pugnac,O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino-Z-N-phenylcarbamate
O-(2-Acetamido-2-deoxy-D-glucopyranosylidenamino) N-phenylcarbamate

Biological Activity

[Description]:

(Z)-PUGNAc is a potent O-GlcNAcase inhibitor. (Z)-PUGNAc is a vastly more potent inhibitor of O-GlcNAcase than the E form[1].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Metabolic Disease

[In Vitro]

(Z)-PUGNAc amplifies the incorporation of O-GlcNAc on proteins within both HeLa and HEK cell systems[1].

[References]

[1]. Perreira M, et al. Inhibition of O-GlcNAcase by PUGNAc is dependent upon the oxime stereochemistry. Bioorg Med Chem. 2006;14(3):837-846.

Chemical & Physical Properties

[ Density]:
1.53g/cm3

[ Melting Point ]:
172-175°C

[ Molecular Formula ]:
C₁₅H₁₉N₃O₇

[ Molecular Weight ]:
353.33

[ Exact Mass ]:
353.12200

[ PSA ]:
149.71000

[ Index of Refraction ]:
1.638

[ Storage condition ]:
-20℃

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Carbamidomethylation Side Reactions May Lead to Glycan Misassignments in Glycopeptide Analysis.

Anal. Chem. 87 , 6297-302, (2015)

Iodoacetamide is perhaps the most widely used reagent for the alkylation of free sulfhydryls in proteomic experiments. Here, we report that both incomplete derivatization of Cys side chains and overal...

The Role of PTP1B O-GlcNAcylation in Hepatic Insulin Resistance.

Int. J. Mol. Sci. 16 , 22856-69, (2015)

Protein tyrosine phosphatase 1B (PTP1B), which can directly dephosphorylate both the insulin receptor and insulin receptor substrate 1 (IRS-1), thereby terminating insulin signaling, reportedly plays ...

Glucosamine-induced Sp1 O-GlcNAcylation ameliorates hypoxia-induced SGLT dysfunction in primary cultured renal proximal tubule cells.

J. Cell Physiol. 229(10) , 1557-68, (2014)

The aim of this study is to determine whether GlcN could recover the endoplasmic reticulum (ER) stress-induced dysfunction of Na(+) /glucose cotransporter (SGLT) in renal proximal tubule cells (PTCs) ...