14215-68-0

Basic information

• Product Name: N-Acetyl-D-galactosamine
• Synonyms: 2-(acetylamino)-2-deoxy-alpha-d-galactopyranos;2-ACETAMIDO-2-DESOXY-D-GALACTOPYRANOSE;2-ACETAMIDO-2-DEOXY-D-GALACTOPYRANOSE;ALPHA-N-ACETYLGALACTOSAMINIDASE;ACETAMIDO-2-DEOXY-D-GALACTOPYRANOSE, 2-;ACETAMIDO-2-DEOXY-D-GALACTOSE;ACETYL-D-GALACTOSAMINE;ACETYLCHONDROSAMINE
• CAS NO: 14215-68-0
• Molecular Formula: C₈H₁₅NO₆
• Molecular Weight: 221.21
• EINECS: 217-321-9
• Product Categories: Aminosugars;Biochemistry;Galactose;Sugars;Dextrins、Sugar & Carbohydrates
• Mol File: 14215-68-0.mol
• Article Data: 95

Chemical Properties

• Melting Point: 158-162 °C
• Boiling Point: 362.26°C (rough estimate)
• Flash Point: 313.9 °C
• Appearance: white to off-white fine crystalline powder
• Density: 1.3572 (rough estimate)
• Vapor Pressure: 7.12E-19mmHg at 25°C
• Refractive Index: 85 ° (C=1, H2O)
• Storage Temp.: 2-8°C
• Solubility: Methanol (Slightly, Sonicated), Water (Slightly)
• PKA: 12.04±0.70(Predicted)
• Water Solubility: almost transparency
• CAS DataBase Reference: N-Acetyl-D-galactosamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Acetyl-D-galactosamine(14215-68-0)
• EPA Substance Registry System: N-Acetyl-D-galactosamine(14215-68-0)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 14215-68-0(Hazardous Substances Data)

Usage

Description

N-Acetyl-D-galactosamine is a white to off-white fine crystalline powder that serves as a bio-activated reporter for visualization purposes in various applications.

Uses

Used in Research and Diagnostics:
N-Acetyl-D-galactosamine is used as a bio-activated reporter for the visualization of specific biological processes and interactions. Its application in this field is due to its ability to be activated and detected within biological systems, providing valuable insights into cellular and molecular mechanisms.
Used in Pharmaceutical Industry:
N-Acetyl-D-galactosamine is used as a key component in the development of pharmaceuticals targeting various diseases. Its application in this industry is attributed to its potential role in modulating biological pathways and its compatibility with drug delivery systems, which can enhance its bioavailability and therapeutic outcomes.
Used in Drug Delivery Systems:
In the field of drug delivery, N-Acetyl-D-galactosamine is used as a component in the design and development of novel drug delivery systems. Its application in this area is due to its ability to enhance the delivery, bioavailability, and therapeutic outcomes of various pharmaceutical agents, particularly in the context of cancer treatment and other diseases.
Used in Biotechnology:
N-Acetyl-D-galactosamine is employed as a vital component in biotechnological applications, such as the development of biosensors and diagnostic tools. Its application in this industry is based on its ability to interact with specific biological molecules and its compatibility with various detection methods, making it a valuable tool for monitoring and analyzing biological processes.

Enzyme inhibitor

This acetylated aminosugar (FW = 221.21 g/mol), also known as 2acetamido-2-deoxy-D-galactopyranose and abbreviated D-GalpNAc and NAGA, is a component of many glycoproteins, chondroitin, and bloodgroup substances. N-Acetyl-D-galactosamine will also inhibit the binding of ligands to many lectins. Target(s): b-N-acetylhexosaminidase; a-N-acetylgalactosaminidase; discoidins I and II, or Dictyostelium discoideum agglutinins; Bauhinia purpurea agglutinin; lima bean (Phaseolus lunatus) lectin; Wistaria floribunda phytomitogen; horse gram (Dolichos biflorus) lectin; Sophora japonica hemagglutinin; soybean (Glycine max) agglutinin; snail (Helix pomatia) hemagglutinin; a-galactosidase B; b-N-acetylglucosaminidase; b-N-acetylgalactosaminidase; galactose oxidase, also alternative substrate; keratan sulfotransferase, weakly inhibited; aralin; rRNA N-glycosylase; peptidoglycan b-N-acetylmuramidase; polypeptide N acetylgalactosaminyltransferase.

InChI:InChI=1/C8H15NO6/c1-4(12)9-5(2-10)7(14)8(15)6(13)3-11/h2,5-8,11,13-15H,3H2,1H3,(H,9,12)/t5-,6+,7-,8+/m0/s1

Upstream product

• 117177-19-2 2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline 
• 19342-33-7 N-acetyl neuraminic acid 
• 528-04-1 uridine 5'-diphospho-N-acetylglucosamine 
• 42890-21-1 2-acetamido-2-deoxy-D-mannose diethyl dithioacetal 
• 7732-18-5 water 
• 2776-93-4 2-acetamido-1-N-(L-β-aspartyl)-2-deoxy-β-D-glucopyranosylamine 
• 120489-33-0 methyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-α-D-glucopyranoside 
• 80265-04-9 4-methylumbelliferyl 2-acetamido-2-deoxy-α-D-glucopyranoside 
• 22595-97-7 2-acetamido-2-deoxy-3,4:5,6-di-O-isopropylidene-aldehydo-D-glucose 
• 3459-18-5 4-nitrophenyl N-acetyl-β-D-glucosaminide 
• 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 
• 4239-72-9 ethyl 2-acetamido-3,4,6-tetra-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside 
• 33289-65-5 2-acetamido-6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-D-glucopyranoside 

Downstream Products

• 98-01-1 furfural 
• 141-46-8 Glycolaldehyde 
• 28876-37-1 2-acetamido-2-deoxy-D-mannono-1,4-lactone 
• 3006-60-8 1,3,4,6-tetra-O-acetyl-2-acetamido-2-deoxy-α,β-D-mannopyranose 
• 131-48-6 N-Acetylneuraminic acid 
• 58718-38-0 (2S,4S,5R,6R)-5-Acetylamino-6-[(R)-1,2-dihydroxy-3-(2-hydroxy-propionyloxy)-propyl]-2,4-dihydroxy-tetrahydro-pyran-2-carboxylic acid 
• 209977-51-5 β-D-galactopyranosyl-(1->6)-2-acetamido-2-deoxy-β-D-mannopyranose 
• 209977-51-5 β-D-galactopyranosyl-(1->6)-2-acetamido-2-deoxy-α-D-mannopyranose 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 58546-02-4 2-acetamido-2,3-dideoxy-α-D-erythro-hex-2-enofuranose 
• 1262206-14-3 2-acetamido-3,6-anhydro-2-deoxy-β-D-mannofuranose 
• 34972-56-0 2-acetamido-3,6-anhydro-2-deoxy-α-D-mannofuranose 
• 144846-62-8 2-acetamido-3,6-anhydro-2-deoxy-β-D-glucofuranose 
• 144846-61-7 2-acetamido-3,6-anhydro-2-deoxy-α-D-glucofuranose 

Relevant articles and documents

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.