O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI Struktur

O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI

Bezeichnung:O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI

CAS-Nr132489-69-1

Englisch Name:O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI

CBNumberCB5503122

SummenformelC15H19N3O7

Molgewicht353.33

MOL-Datei132489-69-1.mol

O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI physikalisch-chemischer Eigenschaften

Schmelzpunkt	172-175°C
Dichte	1.53
storage temp.	-20°C
Löslichkeit	Soluble in DMSO (up to 35 mg/ml)
Aggregatzustand	solid
pka	11.85±0.70(Predicted)
Farbe	White
BRN	4274031
Stabilität	Moisture and Temperature Sensitive

Sicherheit

WGK Germany	3
HS Code	29329990

Gefahreninformationscode (GHS)

O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
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.
Chemische Eigenschaften
White to Off-White Solid
Verwenden
An inhibitor of O-GlcNAcase, hexosaminidase A, and hexosaminidase B
Verwenden
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.
Biologische Aktivität
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).
Lager
Desiccate at -20°C
Einzelnachweise
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 Upstream-Materialien And Downstream Produkte

O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

132489-69-1, O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI Verwandte Suche:

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