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| O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI Basic information |
| Product Name: | O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI | | Synonyms: | 2-(AcetylaMino)-2-deoxy-N-[[(phenylaMino)carbonyl]oxy]-D-gluconiMidic Acid δ-Lactone;(1Z)-2-(Acetylamino)-2-deoxy-N-[[(phenylamino)carbonyl]oxy]-D-gluconimidic acid delta-lactone;n-acetylglucosaminono-1,5-lactoneo-(phenylcarbamoyl)oxime;acetamidodeoxy-D-glucopyranosylideneamino phenylcarbamate;O-(2-Acetamido-2-deoxy-D-glucopyranosylidenamino) N-phenylcarbamate;(Z)-Pugnac;O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino-Z-N-phenylcarbamate;O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenyl carbamate ,97% | | CAS: | 132489-69-1 | | MF: | C15H19N3O7 | | MW: | 353.33 | | EINECS: | 1533716-785-6 | | Product Categories: | Carbohydrates & Derivatives;Glycosidase Inhibitors;Inhibitors | | Mol File: | 132489-69-1.mol |
| O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI Chemical Properties |
| Melting point | 172-175°C | | density | 1.53 | | storage temp. | -20°C | | solubility | Soluble in DMSO (up to 35 mg/ml) | | form | solid | | pka | 11.85±0.70(Predicted) | | color | White | | BRN | 4274031 | | Stability: | Moisture and Temperature Sensitive |
| WGK Germany | 3 | | HS Code | 29329990 |
| O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI Usage And Synthesis |
| Description | Proteins can be modified post-translationally by the addition of O-linked N-acetylglucosamine (O-GlcNAc). Nuclear cytoplasmic O-GlcNAcase and acetyltransferase (NCOAT) is a β-N-acetylglucosaminidase that removes GlcNAc from O-glycosylated proteins. PUGNAc is a (phenylcarbamoyl)oxime analog of GlcNAc that reversibly inhibits NCOAT (Ki = 40-110 nM). It also less potently inhibits other hexosaminidases and exochitinases. (Z)-PUGNAc is a stereoisomer of PUGNAc that is a more potent inhibitor of NCOAT than the (E) isomer, both in vitro and in cells. | | Chemical Properties | White to Off-White Solid | | Uses | An inhibitor of O-GlcNAcase, hexosaminidase A, and hexosaminidase B | | Uses | 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. | | Biological Activity | O -GlcNAc- β - N -acetylglucosaminidase ( O -GlcNAcase) and β -hexosaminidase inhibitor (K i 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. | | 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). | | References | 1) Macauley et al. (2005), O-GlcNAcase uses substrate-assisted catalysis: kinetic analysis and development of highly selective mechanism-inspired inhibitors; J. Biol. Chem., 280 25313
2) Kneass and Marchase (2005), Protein O-GlcNAc modulates motility-associated signaling intermediates in neutrophils; J. Biol. Chem., 280 14579
3) Zou et al. (2007), The protective effects of PUGNAC on cardiac function after trauma-hemorrhage are mediated via increased protein O-GlcNAc levels; Shock, 27 402
4) Arias et al. (2004), Prolonged incubation in PUGNAc results in increased protein O-Linked glycosylation and insulin resistance in rat skeletal muscle; Diabetes, 53 921 |
| O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI Preparation Products And Raw materials |
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