| Identification | Back Directory | [Name]
O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI | [CAS]
132489-69-1 | [Synonyms]
(Z)-Pugnac
(Z)-PUGNAc min. 99%
O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI
n-acetylglucosaminono-1,5-lactoneo-(phenylcarbamoyl)oxime
acetamidodeoxy-D-glucopyranosylideneamino phenylcarbamate
O-(2-Acetamido-2-deoxy-D-glucopyranosylidenamino) N-phenylcarbamate
O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino-Z-N-phenylcarbamate
(Z)-O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate
O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenyl carbamate ,97%
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
D-Gluconimidic acid, 2-(acetylamino)-2-deoxy-N-[[(phenylamino)carbonyl]oxy]-, δ-lactone, (1Z)-
(5R,6R,7S,8R,Z)-6,7-Dihydroxy-8-(hydroxymethyl)-2,3-dioxo-N-((phenylcarbamoyl)oxy)-1,4-oxazocane-5-carbimidic acid | [EINECS(EC#)]
1533716-785-6 | [Molecular Formula]
C15H19N3O7 | [MDL Number]
MFCD00145022 | [MOL File]
132489-69-1.mol | [Molecular Weight]
353.33 |
| Chemical Properties | Back Directory | [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 | [InChIKey]
PBLNJFVQMUMOJY-GJXDPMCDNA-N | [SMILES]
C1(=N/OC(=O)NC2C=CC=CC=2)/O[C@@H]([C@@H](O)[C@H](O)[C@H]/1NC(=O)C)CO |&1:13,14,16,18,r| |
| Hazard Information | Back Directory | [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).1,2 It also less potently inhibits other hexosaminidases and exochitinases.2,3,4 (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.5 | [Chemical Properties]
White to Off-White Solid | [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. | [Uses]
An inhibitor of O-GlcNAcase, hexosaminidase A, and hexosaminidase B | [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). | [storage]
Desiccate at -20°C | [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 |
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