ChemicalBook > CAS DataBase List > O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI

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;PugNAc, hexosaminidase A and B inhibitor;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
CBNumber
CB5503122
Molecular Formula
C15H19N3O7
Formula Weight
353.33
MOL File
132489-69-1.mol
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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
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Safety

WGK Germany 
3
HS Code 
29329990
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
A7229
Product name
PUGNAc
Purity
≥95% (HPLC)
Packaging
5mg
Price
$198
Updated
2024/03/01
Sigma-Aldrich
Product number
A7229
Product name
PUGNAc
Purity
≥95% (HPLC)
Packaging
10mg
Price
$369
Updated
2024/03/01
Cayman Chemical
Product number
17151
Product name
(Z)-PUGNAc
Purity
≥95%
Packaging
1mg
Price
$32
Updated
2024/03/01
Cayman Chemical
Product number
17151
Product name
(Z)-PUGNAc
Purity
≥95%
Packaging
5mg
Price
$139
Updated
2024/03/01
Cayman Chemical
Product number
17151
Product name
(Z)-PUGNAc
Purity
≥95%
Packaging
10mg
Price
$214
Updated
2024/03/01
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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

O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI Preparation Products And Raw materials

Raw materials

Preparation Products

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

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View Lastest Price from O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
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
Career Henan Chemical Co
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

132489-69-1, O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLIRelated Search:

3-METHYLADENINE Tris(2-carboxyethyl)phosphine hydrochloride CAL-101 PHOSPHATIDYLETHANOL AMINO ACID HYDROXAMATES DL-NORVALINE HYDROXAMATE 2-ACETAMIDO-2-DEOXY-D-GLUCONHYDROXIMO-1,5-LACTONE 4-HYDROXY-BUTYRIMIDIC ACID ETHYL ESTER 5-HYDROXYPENTANAL OXIME AMINO ACID HYDROXAMATES DL-SERINE HYDROXAMATE Ethyl acetohydroxamate AMINO ACID HYDROXAMATES GLYCINE HYDROXAMATE O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI AMINO ACID HYDROXAMATES DL-THREONINE HYDROXAMATE

  • 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
  • n-acetylglucosaminono-1,5-lactoneo-(phenylcarbamoyl)oxime
  • acetamidodeoxy-D-glucopyranosylideneamino phenylcarbamate
  • O-(2-Acetamido-2-deoxy-D-glucopyranosylidenamino) N-phenylcarbamate
  • (Z)-Pugnac
  • O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino-Z-N-phenylcarbamate
  • O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenyl carbamate ,97%
  • (Z)-O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate
  • (Z)-PUGNAc min. 99%
  • O-[2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSYLI
  • (5R,6R,7S,8R,Z)-6,7-Dihydroxy-8-(hydroxymethyl)-2,3-dioxo-N-((phenylcarbamoyl)oxy)-1,4-oxazocane-5-carbimidic acid
  • D-Gluconimidic acid, 2-(acetylamino)-2-deoxy-N-[[(phenylamino)carbonyl]oxy]-, δ-lactone, (1Z)-
  • PUGNAc extrapure, 95%
  • N-((3R,4R,5S,6R,Z)-4,5-Dihydroxy-6-(hydroxymethyl)-2-(((phenylcarbamoyl)oxy)imino)tetrahydro-2H-pyran-3-yl)acetamide
  • (2Z,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-ylidene]amino N-phenylcarbamate
  • PugNAc, hexosaminidase A and B inhibitor
  • 132489-69-1
  • Carbohydrates & Derivatives
  • Glycosidase Inhibitors
  • Inhibitors