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

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|

Safety Information

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 (K_i = 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] MATTHEW S MACAULEY. O-GlcNAcase uses substrate-assisted catalysis: kinetic analysis and development of highly selective mechanism-inspired inhibitors.[J]. The Journal of Biological Chemistry, 2005, 280 27: 25313-25322. DOI:10.1074/jbc.m413819200
[2] ZACHARY T KNEASS  Richard B M. Protein O-GlcNAc modulates motility-associated signaling intermediates in neutrophils.[J]. The Journal of Biological Chemistry, 2005: 14579-14585. DOI:10.1074/jbc.m414066200
[3] LUYUN ZOU. The protective effects of PUGNAc on cardiac function after trauma-hemorrhage are mediated via increased protein O-GlcNAc levels.[J]. SHOCK, 2007, 27 4: 402-408. DOI:10.1097/01.shk.0000245031.31859.29
[4] EDWARD B ARIAS  Gregory D C  Junghoon Kim. Prolonged incubation in PUGNAc results in increased protein O-Linked glycosylation and insulin resistance in rat skeletal muscle.[J]. Diabetes, 2004, 53 4: 921-930. DOI:10.2337/diabetes.53.4.921

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