14131-68-1

Basic information

• Product Name: 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOSAMINE
• Synonyms: 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOSAMINE;2-Acetamido-2-deoxy-b-D-glucopyranosylamine;N-[(2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide;N-Acetyl-b-D-glucosamine;2-Acetamido-2-deoxy-beta-D-glucopyranosylamine;N-((2R,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxyMethyl)tetrahydro-2H-pyran-3-yl)acetaMide
• CAS NO: 14131-68-1
• Molecular Formula: C₈H₁₅NO₆
• Molecular Weight: 220.22
• EINECS: 231-368-2
• Mol File: 14131-68-1.mol
• Article Data: 103

Chemical Properties

• Melting Point: 182-183.5 °C
• Boiling Point: 595.4°C at 760mmHg
• Flash Point: 313.9°C
• Appearance: /
• Density: 1.5g/cm³
• Vapor Pressure: 1.18E-16mmHg at 25°C
• Refractive Index: 1.575
• PKA: 12.04±0.70(Predicted)
• CAS DataBase Reference: 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOSAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOSAMINE(14131-68-1)
• EPA Substance Registry System: 2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOSAMINE(14131-68-1)

Safety Data

• Hazardous Substances Data: 14131-68-1(Hazardous Substances Data)

Usage

General Description

2-Acetamido-2-deoxy-beta-D-glucosamine, also known as N-acetylglucosamine (GlcNAc), is a naturally occurring amino sugar and a derivative of glucose. It is an important component of the structural polysaccharides chitin and hyaluronic acid, as well as being a key component of the cell wall of many bacteria and fungi. GlcNAc is also involved in various biological processes, including cell signaling, immunomodulation, and as a precursor for the biosynthesis of glycosylated proteins, lipids, and other important biomolecules. It has been studied for its potential therapeutic applications in treating conditions such as osteoarthritis, inflammatory bowel disease, and skin disorders due to its anti-inflammatory and immunomodulatory properties. Additionally, GlcNAc has been investigated for its potential use in biotechnology and medicine as a building block for chemoenzymatic synthesis and as a therapeutic agent for various diseases.

InChI:InChI=1/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8-/m1/s1

Upstream product

• 64-19-7 acetic acid 
• 219727-01-2 p-nitrophenyl 2-amino-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside 
• 33289-65-5 2-acetamido-6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-D-glucopyranoside 
• 13088-77-2 N,N',N'',N'''-tetraacetylchitotetraose 
• 1240317-45-6 2-acetamido-2-deoxy-β-D-glucopyranosyl-1H-1,2,3-triazole 
• 67-56-1 methanol 
• 72-87-7 N-acetyl-D-mannosamine 
• 7284-16-4 p-nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranoside 
• 22595-97-7 2-acetamido-2-deoxy-3,4:5,6-di-O-isopropylidene-aldehydo-D-glucose 
• 97055-07-7 1-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-acetylhydrazine 
• 117177-19-2 2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline 

Downstream Products

• 10486-91-6 2-acetamido-2-deoxy-D-galacticol 
• 21559-73-9 cyclohexyl 2-(acetylamino)-2-deoxy-α-D-glucopyranoside 
• 22256-76-4 methyl 2-acetamido-2-deoxy-β-D-galactopyranoside 
• 6082-22-0 methyl α-D-N-acetylgalactosamine 
• 3006-60-8 1,3,4,6-tetra-O-acetyl-2-acetamido-2-deoxy-α,β-D-mannopyranose 
• 155544-65-3 2-acetamido-5,6-di-O-acetyl-2,3-didehydro-2,3-dideoxy-D-threo-hexono-1,4-lactone 
• 6959-53-1 2-acetamido-2-deoxy-6-O-trityl-D-galactose 
• 3554-93-6 benzyl 2-acetamido-2-deoxy-α-D-galactopyranoside 
• 3055-51-4 benzyl 2-deoxy-2-(N-acetylamino)-D-glucopyranoside 
• 3055-51-4 benzyl 2-acetamido-2-deoxy-β-D-glucopyranoside 
• 13343-62-9 benzyl 2-acetamido-2-deoxy-α-D-glucopyranoside 
• 147126-58-7 octyl 2-(acetylamino)-2-deoxy-β-D-glucopyranoside 
• 147126-57-6 octyl 2-N-acetyl-2-amino-2-deoxy-α-D-glucopyranoside 
• 54400-75-8 allyl 2-acetamido-2-deoxy-β-D-glucopyranoside 

Relevant articles and documents

Structure of the major O-specific polysaccharide from the lipopolysaccharide of Pseudomonas fluorescens BIM B-582: Identification of 4-deoxy-d-xylo-hexose as a component of bacterial polysaccharides

A novel constituent of bacterial polysaccharides, 4-deoxy-d-xylo-hexose (d-4dxylHex), was found in the major O-specific polysaccharide from the lipopolysaccharide of Pseudomonas fluorescens BIM B-582. d-4dxylHex was isolated in the free state by paper chromatography after full acid hydrolysis of the polysaccharide and identified by GLC-mass spectrometry, 1H and 13C NMR spectroscopy, and specific rotation. It occurs as a lateral substituent in ～40% of the oligosaccharide repeating units, making the polysaccharide devoid of strict regularity. The structure of the polysaccharide was established by sugar analysis, Smith degradation, and two-dimensional 1H and 13C NMR spectroscopy. In addition, a minor polysaccharide was isolated from the same lipopolysaccharide and found to contain 4-O-methylrhamnose.

Synthesis and anti-acetylcholinesterase activities of novel glycosyl coumarylthiazole derivatives

Eleven glycosyl coumarylthiazole derivatives are synthesized by cyclization and condensation of glycosyl thiourea with 3-bromoacetyl coumarins in ethanol. The reaction conditions are optimized and good yields of products (80%–95%) are obtained. The structures of all new products were confirmed by IR, 1H and 13C NMR, and by HRMS (electrospray ionization). The in vitro acetylcholinesterase (AChE) inhibitory activities of these new compounds are tested by Ellman’s method. Among them, N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-(6-nitrocoumarinyl)-1,3-thiazole-2-amine showed the best activity with an in vitro AChE inhibitory rate of 58% and an IC50 value of 12 ± 0.38 μg/mL.

Synthesis and anticholinesterase activities of novel glycosyl benzoxazole derivatives

Eight glycosyl benzoxazole derivatives are synthesized by nucleophilic addition reactions of glycosyl isothiocyanate with o-aminophenol in tetrahydrofuran. The reaction conditions are optimized, and good yields (86%–94%) were obtained. The structures of all new products are confirmed by infrared, 1H nuclear magnetic resonance, and high-resolution mass spectrometry (electrospray ionization). In addition, the in vitro cholinesterase inhibitory activities of these new compounds are tested by Ellman’s method.

Biochemical Characterization and Structural Analysis of a β- N-Acetylglucosaminidase from Paenibacillus barengoltzii for Efficient Production of N-Acetyl- d -glucosamine

Bioproduction of N-acetyl-d-glucosamine (GlcNAc) from chitin, the second most abundant natural renewable polymer on earth, is of great value in which chitinolytic enzymes play key roles. In this study, a novel glycoside hydrolase family-18 β-N-acetylglucosaminidase (PbNag39) from Paenibacillus barengoltzii suitable for GlcNAc production was identified and biochemically characterized. It possessed a unique shallow catalytic groove (5.8 ?) as well as a smaller C-terminal domain (solvent-accessible surface area, 5.1 × 103 ?2) and exhibited strict substrate specificity toward N-acetyl chitooligosaccharides (COS) with GlcNAc as the sole product, showing a typical manner of action of β-N-acetylglucosaminidases. Thus, an environmentally friendly bioprocess for GlcNAc production from ball-milled powdery chitin by an enzyme cocktail reaction was further developed. By using the new route, the powdery chitin conversion rate increased from 23.3% (v/v) to 75.3% with a final GlcNAc content of 22.6 mg mL-1. The efficient and environmentally friendly bioprocess may have great application potential in GlcNAc production.