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(Z)-PugnacInhibitor of O-GlcNAcase and β-hexosaminidase

(Z)-Pugnac

Catalog No. BCC5333
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Quality Control of (Z)-Pugnac

Chemical structure

(Z)-Pugnac

Biological Activity of (Z)-Pugnac

O-GlcNAc-β-N-acetylglucosaminidase (O-GlcNAcase) and β-hexosaminidase inhibitor (Ki values are 46 and 36 nM respectively) that increases O-GlcNAc levels ~ 2-fold in HT29 cells. Z-linked isomer is more potent than the E isomer.

(Z)-Pugnac Dilution Calculator

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Chemical Properties of (Z)-Pugnac

Cas No. 132489-69-1 SDF Download SDF
Chemical Name O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino-Z-N-phenylcarbamate
SMILES CC(=O)N[C@@H]/1[C@@H](O)[C@H](O)[C@@H](CO)OC1=N/OC(=O)Nc2ccccc2
Standard InChIKey PBLNJFVQMUMOJY-JXZOILRNSA-N
Standard InChI 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
Formula C15H19N3O7 M.Wt 353.33
Solubility Soluble to 100 mM in DMSO
Storage Desiccate at -20°C
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other courier with RT , or blue ice upon request.

Preparing Stock Solutions of (Z)-Pugnac

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.8302 mL 14.1511 mL 28.3022 mL 56.6043 mL 70.7554 mL
5 mM 0.566 mL 2.8302 mL 5.6604 mL 11.3209 mL 14.1511 mL
10 mM 0.283 mL 1.4151 mL 2.8302 mL 5.6604 mL 7.0755 mL
50 mM 0.0566 mL 0.283 mL 0.566 mL 1.1321 mL 1.4151 mL
100 mM 0.0283 mL 0.1415 mL 0.283 mL 0.566 mL 0.7076 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

Background on (Z)-Pugnac

(Z)-Pugnac is a potent inhibitor of O-GlcNAcase [1].

Pugnac is an inhibitor of O-GlcNAcase and is initially found to be an inhibitor of β-N-acetylglucosaminidases. It plays its inhibition role through mimicking the substrates of its target enzymes.(Z)-Pugnac is the Z stereoisomer of Pugnac. It is found to be more potent than the E stereoisomer. When tested with the recombinant O-GlcNAcase and the fluorogenic substrate, (Z)-Pugnac inhibited approximately 80% of O-GlcNAcase native activity at concentration of 1 μM. (E)-Pugnac at the same concentration showed only 10% inhibition of the activity. Besides that, (Z)-Pugnac induced about 1.4-fold increased level of O-GlcNAc incorporation on proteins both in HEK cells and in HeLa cells [1].

References:
[1] Perreira M, Kim E J, Thomas C J, et al. Inhibition ofO-GlcNAcase by PUGNAc is dependent upon the oxime stereochemistry. Bioorganic & medicinal chemistry, 2006, 14(3): 837-846.

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