O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI
- CAS NO.:132489-69-1
- Empirical Formula: C15H19N3O7
- Molecular Weight: 353.33
- MDL number: MFCD00145022
- EINECS: 1533716-785-6
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-06-30 15:45:59
What is O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI?
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
The Uses of O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI
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.
The Uses of O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI
An inhibitor of O-GlcNAcase, hexosaminidase A, and hexosaminidase B
What are the applications of Application
(Z)-Pugnac is an O-GlcNAcase inhibitor that undergoes Beckmann rearrangement to promote insulin resistance in adipocytes.
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
Properties of O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI
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 |
Safety information for O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. |
Computed Descriptors for O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI
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