134451-94-8

Basic information

• Product Name: N-ACETYL-D-GLUCOSAMINE
• Synonyms: 2-ACETAMIDO-2-DESOXY-D-GLUCOPYRANOSE;2-ACETAMIDO-2-DEOXY GLUCOPYRANOSE;D-GLCNAC;N-ACETYL-L-GLUCOSAMINE;N-[2,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)TETRAHYDRO-2H-PYRAN-3-YL]ACETAMIDE;N-[(2S,3S,4R,5S)-3,4,5,6-tetrahydroxy-1-oxohexan-2-yl]acetamide
• CAS NO: 134451-94-8
• Molecular Formula: C₈H₁₅NO₆
• Molecular Weight: 221.21
• EINECS: 231-368-2
• Mol File: 134451-94-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: 211 °C (dec.)(lit.)
• Boiling Point: 636.4°C at 760 mmHg
• Flash Point: 338.7°C
• Appearance: white to off-white/powder
• Density: 1.423g/cm³
• Vapor Pressure: 7.12E-19mmHg at 25°C
• Refractive Index: 1.541
• Storage Temp.: −20°C
• Solubility: H2O: 50 mg/mL colorless to faint yellow solution, clear to
• PKA: 13.04±0.20(Predicted)
• Water Solubility: H2O: 50 mg/mL colorless to faint yellow solution, clear to very slightly hazy
• CAS DataBase Reference: N-ACETYL-D-GLUCOSAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-ACETYL-D-GLUCOSAMINE(134451-94-8)
• EPA Substance Registry System: N-ACETYL-D-GLUCOSAMINE(134451-94-8)

Safety Data

• Hazard Codes: Xi:
• Safety Statements: S24/25:
• WGK Germany: 3
• RTECS: LZ6651000
• F: 3-10
• Hazardous Substances Data: 134451-94-8(Hazardous Substances Data)

Usage

Chemical Description

N-acetyl-D-glucosamine is a monosaccharide that is a component of chitin and is also found in the glycoproteins and glycolipids of many organisms.

Uses

Used in Pharmaceutical Industry:
N-ACETYL-D-GLUCOSAMINE is used as a building block for the synthesis of various complex carbohydrates and glycoproteins, which are crucial for the proper functioning of cells and tissues. Its role in the pharmaceutical industry is to serve as a key component in the development of drugs targeting specific cellular processes and interactions.
Used in Research and Development:
In the field of research and development, N-ACETYL-D-GLUCOSAMINE is used as a valuable compound for studying the structure, function, and biosynthesis of carbohydrates and glycoproteins. It aids in understanding the molecular mechanisms underlying various biological processes and diseases, contributing to the advancement of medical and biological knowledge.
Used in Diagnostic Applications:
N-ACETYL-D-GLUCOSAMINE can be employed as a diagnostic marker or component in the development of diagnostic tools and tests. Its presence or levels in biological samples can provide valuable information about the status of certain cellular processes or the presence of specific diseases, aiding in the early detection and monitoring of various health conditions.
Used in Nutritional Supplements:
As a naturally occurring amino sugar, N-ACETYL-D-GLUCOSAMINE may be used as an ingredient in nutritional supplements, particularly those targeting joint health and mobility. Its role in the synthesis of glycosaminoglycans, which are essential components of cartilage, makes it a potential candidate for supporting joint health and reducing inflammation.
Used in Cosmetics Industry:
In the cosmetics industry, N-ACETYL-D-GLUCOSAMINE may be utilized for its potential skin conditioning and moisturizing properties. Its ability to interact with proteins and other cellular components can contribute to the development of products that improve skin hydration, elasticity, and overall health.
Used in Food Industry:
N-ACETYL-D-GLUCOSAMINE can be used in the food industry as a natural sweetener or as an ingredient in the development of functional foods. Its role in cellular processes and its potential health benefits make it a valuable component in the creation of products that promote overall health and well-being.

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)

Upstream product

• 84012-04-4 α-L-Fuc-(1-3)-β-D-GalNAc-(1-3)-β-D-Gal-(1-4)-β-D-Gal-(1-3)-D-GalNAc-ol 
• 1948-54-5 D-galactosamine 
• 7512-17-6 2-acetamido-2-deoxy-D-glucose 
• 72879-11-9 N-[(2R,3R,4R,5R,6R)-2-((S)-2,3-Dihydroxy-propoxy)-5-hydroxy-6-hydroxymethyl-4-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide 
• 108-24-7 acetic anhydride 

Downstream Products

• 1234099-38-7 C₄₁H₆₆N₂O₁₀ 
• 3554-90-3 β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-D-galactose 
• 71023-10-4 sialyl-T antigen 

Relevant articles and documents

N-acetyltransferases from three different organisms displaying distinct selectivity toward hexosamines and N-terminal amine of peptides

N-acetyltransferases are a family of enzymes that catalyze the transfer of the acetyl moiety (–COCH3) from acetyl coenzyme A (Acetyl-CoA) to a primary amine of acceptor substrates from small molecules such as aminoglycoside to macromolecules of various proteins. In this study, the substrate selectivity of three N-acetyltransferases falling into different phylogenetic groups was probed against a series of hexosamines and synthetic peptides. GlmA from Clostridium acetobutylicum and RmNag from Rhizomucor miehei, which have been defined as glucosamine N-acetyltransferases, were herein demonstrated to be also capable of acetylating the free amino group on the very first glycine residue of peptide in spite of varied catalytic efficiency. The human recombinant N-acetyltransferase of Naa10p, however, prefers primary amine groups in the peptides as opposed to glucosamine. The varied preference of GlmA, RmNag and Naa10p probably arose from the divergent evolution of these N-acetyltransferases. The expanded knowledge of acceptor specificity would as well facilitate the application of these N-acetyltransferases in the acetylation of hexosamines or peptides.

Structure and antioxidant activity study of sulfated acetamido- polysaccharide from Radix Hedysari

A new sulfated acetamido-heteropolysaccharide, HPS4-2A, was obtained by aqueous extraction followed by precipitation with ethanol and fractionation with DEAE column chromatography from Radix Hedysari. It was composed of rhamnose, arabinose, glucose, galactose and 2-acetamido-2-deoxy-D-galactose in the molar ratio of 10.09%:25.90%:25.90%:25.0%:12.30%. Elemental analysis indicated that HPS4-2A was a sulfated polysaccharide containing small amount of sulfate groups (1.87%). Partial acid hydrolysis, GC, GC-MS, 1D and 2D NMR spectroscopy analysis of the HPS4-2A revealed a predominance of glucose, galactose and 2-acetamido-2-deoxy-D-galactose linked in a highly-branched structure. Themolecular weight of HPS4-2Awas determined by HPSEC and HPSEC-MALLS. AFMstudy indicated that HPS4-2A took a highly branched conformation, which in consistent with the result studied by SEC-MALLS. Structural features of HPS4-2A were also investigated by SEM and TEM. Antioxidant assays demonstrated that HPS4-2A possessed of strong DPPH and hydroxyl radicals scavenging activities, suggesting that HPS4-2A could potentially be used as natural antioxidant.

Structure elucidation of the O-antigen of Salmonella enterica O51 and its structural and genetic relation to the O-antigen of Escherichia coli O23

The O-polysaccharide (O-antigen) of Salmonella enterica O51 was isolated by mild acid degradation of the lipopolysaccharide and its structure was established using sugar analysis and NMR spectroscopy. The O-antigen of Escherichia coli O23, whose structure was elucidated earlier, possesses a similar structure and differs only in the presence of an additional lateral α-D-Glcp residue at position 6 of the GlcNAc residue in the main chain. Sequencing of the O-antigen gene clusters of S. enterica O51 and E. coli O23 revealed the same genes with a high-level similarity. By comparison with opened gene databases, all genes expected for the synthesis of the common structure of the two O-antigens were assigned functions. It is suggested that the gene clusters of both bacteria originated from a common ancestor, whereas the O-antigen modification in E. coli O23, which, most probably, is induced by prophage genes outside the gene cluster, could be introduced after the species divergence.

One-pot enzymatic production of 2-acetamido-2-deoxy-D-galactose (GalNAc) from 2-acetamido-2-deoxy-D-glucose (GlcNAc)

2-Acetamido-2-deoxy-D-galactose (GalNAc) is a common monosaccharide found in biologically functional sugar chains, but its availability is often limited due to the lack of abundant natural sources. In order to produce GalNAc from abundantly available sugars, 2-acetamido-2-deoxy-D-glucose (GlcNAc) was converted to GalNAc by a one-pot reaction using three enzymes involved in the galacto-N-biose/lacto-N-biose I pathway of bifidobacteria. Starting the reaction with 600 mM GlcNAc, 170 mM GalNAc was produced at equilibrium in the presence of catalytic amounts of ATP and UDP-Glc under optimized conditions. GalNAc was separated from GlcNAc using water-eluting cation-exchange chromatography with a commonly available cation-exchange resin.

COMPOSITIONS AND METHODS FOR TREATING HEPATITIS-C

New compositions and methods for treating patients suffering from hepatitis-C, AIDS, aberrant apoptosis which include N-acetyl-D-glucosaminyl(β-1-4)-N-Acetyl-muramyl-L-ananyl-D-isoglutamine (GMDP) of at least 98% purity and provided either alone, as an active ingredient of blastolysine, or in combination with an aminosugar such as N-acetyl-glucosamine(NAG). The high purity GMDP has a decreased amount immunogenic impurities and demonstrates cell protection as opposed to solely immunostimulatory effects, while a synergistic cell protective effect is exhibited when GMDP in combined with NAG. The new compositions modulate FasL mediated apoptosis while simultaneously stimulating TNF-α production and further selectively inhibiting TNF-α receptor p55 (TNFR1), providing a treatment for patients suffering from hepatitis-C, AIDS or aberrant apoptosis.

Structural studies of the O-specific side-chain of the lipopolysaccharide from Escherichia coli O 55.

The structure of the O-specific side-chains of the lipopolysaccharide from Escherichia coli O 55 has been investigated, methylation analysis, specific degradations, and n.m.r. spectroscopy being the principal methods used. It is concluded that the O-specific side-chains are composed of pentasaccharide repeating-units having the following structure [where Col stands for colitose (3,6-dideoxy-L-xylo-hexose)].(See formula in text).