O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI
- Product Name
- O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI
- CAS No.
- 132489-69-1
- Chemical Name
- O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI
- Synonyms
- (Z)-Pugnac;(Z)-PUGNAc min. 99%;PUGNAc extrapure, 95%;O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI;acetamidodeoxy-D-glucopyranosylideneamino phenylcarbamate;n-acetylglucosaminono-1,5-lactoneo-(phenylcarbamoyl)oxime;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%
- CBNumber
- CB5503122
- Molecular Formula
- C15H19N3O7
- Formula Weight
- 353.33
- MOL File
- 132489-69-1.mol
O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI Property
- 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
- WGK Germany
- 3
- HS Code
- 29329990
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
N-Bromosuccinimide Price
- Product number
- A7229
- Product name
- PUGNAc
- Purity
- ≥95% (HPLC)
- Packaging
- 5mg
- Price
- $198
- Updated
- 2024/03/01
- Product number
- A7229
- Product name
- PUGNAc
- Purity
- ≥95% (HPLC)
- Packaging
- 10mg
- Price
- $369
- Updated
- 2024/03/01
- Product number
- 17151
- Product name
- (Z)-PUGNAc
- Purity
- ≥95%
- Packaging
- 1mg
- Price
- $32
- Updated
- 2024/03/01
- Product number
- 17151
- Product name
- (Z)-PUGNAc
- Purity
- ≥95%
- Packaging
- 5mg
- Price
- $139
- Updated
- 2024/03/01
- Product number
- 17151
- Product name
- (Z)-PUGNAc
- Purity
- ≥95%
- Packaging
- 10mg
- Price
- $214
- Updated
- 2024/03/01
O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI Chemical Properties,Usage,Production
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).
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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View Lastest Price from O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI manufacturers
- Product
- (Z)-PUGNAc 132489-69-1
- Price
- US $0.00/G
- Min. Order
- 10G
- Purity
- 98%min
- Supply Ability
- 30kg/month
- Release date
- 2023-02-14
- Product
- O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI 132489-69-1
- Price
- US $1.00/kg
- Min. Order
- 1kg
- Purity
- 98%min
- Supply Ability
- 100KG
- Release date
- 2018-12-17