Home > Chiral Compounds> O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-Phenylcarbamate

O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-Phenylcarbamate

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Origin: China

Cas No: 132489-69-1

Specification: 99%min

Min order Quantity: 1 /kg

Supply Ability: 100 mt/month

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Product Description

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CAS No.: 132489-69-1 Formula: C15H19N3O7 Molecular Weight: 353.32700

Description

PUGNAc is a 1,5-hydroximolactone, acting as an inhibitor of a variety of N-acetylhexosaminidases. It was long thought that increased levels of O-GlcNAc in human cells lead to Type II diabetes. O-GlcNAc levels were artificially raised with PUGNAc, which inhibits O-GlcNAcase, a beta-exo-N-acetylhexosaminidase which cleaves beta-O-linked-N-acetylglucosamine residues from glycoproteins. As a result of this inhibition, a type II diabetic phenotype was observed. Recent pharmacological studies using a more selective O-GlcNAcase inhibitor did not see this effect. However, genetic manipulation of O-GlcNAc levels is consistent with the effects observed by PUGNAc, namely insulin resistance upon elevation of O-GlcNAc levels.

Basic Info

Chemical Name	O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-Phenylcarbamate
Synonyms	(Z)-Pugnac,O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino-Z-N-phenylcarbamate; O-(2-Acetamido-2-deoxy-D-glucopyranosylidenamino) N-phenylcarbamate;
CAS No.	132489-69-1
Molecular Formula	C15H19N3O7
Molecular Weight	353.32700
PSA	149.71000
LogP	-0.36990

Properties

Density	1.53g/cm3
Refractive Index	1.638
Storage Condition	-20ºC

Synthesis Route

O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate→O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-Phenylcarbamate
phenyl isocyanate→O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-Phenylcarbamate
(Z)-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-gluconohydroximo-1,5-lactone→O-(2-Acetamido-2-deoxy-D-glucopyranosylidene)amino N-Phenylcarbamate

Precursor

phenyl isocyanate
(Z)-2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-gluconohydroximo-1,5-lactone
O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate

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