(Z)-Pugnac CAS: 132489-69-1
MF: C15H19N3O7
MW: 353.33
An O-GlcNAcase inhibitor.

(Z)-Pugnac (CAS 132489-69-1)

(Z)-Pugnac | CAS 132489-69-1 is rated 5.0 out of 5 by 1.
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Synonym: PUGNAc; (Z)-O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate
Application: An O-GlcNAcase inhibitor
CAS Number: 132489-69-1
Purity: ≥99%
Molecular Weight: 353.33
Molecular Formula: C15H19N3O7
* Refer to Certificate of Analysis for lot specific data (including water content).
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(Z)-Pugnac is an inhibitor of NCOAT (O-GlcNAcase), an enzyme which removes the N-acetylglucosamine moieties from 2-acetamido-2-deoxy-β-D-glucopyranose (O-GlcNAc) bound to proteins that were modified by O-GlcNAc. In addition, studies show that (Z)-Pugnac is the more potent inhibitor of O-GlcNAcase than its stereoisomer since it readily undergoes Beckmann rearrangement. Furthermore, (Z)-Pugnac increases the modification of proteins by GlcNAc in adipocytes and decreases insulin-stimulated 2-deoxyglucose (2DG) uptake and GLUT4 translocation in adipocytes, which implies that (Z)-Pugnac promotes insulin resistance in adipocytes. (Z)-Pugnac is an inhibitor of HEXA and HEXB.


References

1. Dong, D.L. and Hart, G.W. 1994. J. Biol. Chem. 269: 19321-19330. PMID: 8034696
2. Park, S.Y., et al. 2005. Exp. Mol. Med. 37: 220-229. PMID: 16000877
3. Perreira, M., et al. 2006. Bioorg. Med. Chem. 14: 837-846. PMID: 16214344

Physical State :
Solid
Solubility :
Soluble in DMSO (100 mM), ethanol (1 mg/ml), hot methanol, and water.
Storage :
Desiccate at -20° C
Melting Point :
171-174° C
Density :
~1.54 g/cm3 (Predicted)
Refractive Index :
n20D 1.64 (Predicted)
IC50 :
&beta-hexosaminidase: IC50 = 6 nM; HeX A/B: IC50 = 25 nM; hOGA: IC50 = 35 nM; OGA: IC50 = 46 nM
Ki Data :
&beta-hexosaminidase: Ki= 36 nM; O-GlcNAcase: Ki= 46 nM
pK Values :
pKa: 11.85 (Predicted), pKb: 0.25 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
9576811
MDL Number :
MFCD00145022
Beilstein Registry :
4274031
SMILES :
CC(=O)N[[email protected]@H]\\1[[email protected]]([[email protected]@H]([[email protected]](O/C1=N\\OC(=O)NC2=CC=CC=C2)CO)O)O

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Certificate of Analysis

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(Z)-Pugnac  Product Citations

See how others have used (Z)-Pugnac. Click on the entry to view the PubMed entry .

Citations 1 to 2 of 2 total

PMID: # 28032764  Wang, Y. et al. 2017. J. Med. Chem. 60: 263-272.

PMID: # 26282597  Kumar, AB. et al. 2015. Clin. Chim. Acta. 451: 125-8.

Citations 1 to 2 of 2 total

Is there any storage information for the product once it's in solution (specifically in DMSO)?

Asked by: two2igm05
Thank you for your question. We recommend that stock solutions of (Z)-Pugnac, sc-204415, are used the same day but generally they should be okay to store at -20º C for a few days.
Answered by: Chemical Support 4
Date published: 2017-04-06
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Rated 5 out of 5 by from Liu Liu, GD. et al. (PubMed 26311324) found that treatment with (Z)-Pugnac, an inhibitor of O-GlcNAcase, reduced glyoxal-induced cell apoptosis. -SCBT Publication Review
Date published: 2015-01-31
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