Tetra-O-acetyl-2-deoxy-D-glucopyranose, CAS:69515-91-9

1,3,4,6-Tetra-O-acetyl-2-deoxy-D-glucopyranose (also known as Ac4-GlcNAc or TAN) is a chemical compound widely used in research labs to study the properties and function of glycoproteins. In this paper, we will go over the definition, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety, applications, current state of research, potential implications in various fields, and limitations and future directions of Ac4-GlcNAc. Synthesis and Characterization: Ac4-GlcNAc is often synthesized from N-acetyl-D-glucosamine (GlcNAc) using acetic anhydride and pyridine as reagents. The synthesis uses a mixture of sulfuric acid and acetic anhydride to acetylate the GlcNAc molecule to create Ac4-GlcNAc. Characterization of the compound is commonly done using Fourier-transform infrared spectroscopy (FTIR), Nuclear magnetic resonance (NMR) spectroscopy, and mass spectroscopy. Analytical Methods: Ac4-GlcNAc is commonly analyzed using chemical methods such as chromatography and spectroscopic methods. High-performance liquid chromatography (HPLC) and thin-layer chromatography (TLC) are commonly used to separate and analyze the compound. Spectroscopic techniques such as NMR and FTIR are used to identify the compounds. Biological Properties: Ac4-GlcNAc is a potent inhibitor of glycogen phosphorylase, an enzyme that plays a critical role in the regulation of glycogen metabolism. Glycogen phosphorylase inhibitors like Ac4-GlcNAc are being tested as potential therapies for type 2 diabetes. Some research has also explored Ac4-GlcNAc's ability to stimulate the production of T-cells in the immune system. Toxicity and Safety in Scientific Experiments: Ac4-GlcNAc is generally considered safe and non-toxic when used in scientific experiments at recommended concentrations. However, researchers should always exercise caution when handling any chemicals and wear proper personal protective equipment. Applications in Scientific Experiments: Ac4-GlcNAc is a versatile and widely used tool in the study of glycoproteins available in various biological systems. Studies have used it to assist in the preparation of glycoprotein molecules for crystallization, to investigate glycoprotein glycosylation processes and to study the processes involved in aging and neurodegenerative diseases. Current State of Research: Several studies have demonstrated the potential therapeutic applications of Ac4-GlcNAc, particularly in the area of glycogen metabolism and glucose regulation. Further studies on its potential therapeutic uses for diabetes and other diseases are ongoing. Potential Implications in Various Fields of Research and Industry: Given its potential applications in glycogen metabolism and glucose regulation, Ac4-GlcNAc could be used for the development of new therapies for diabetes, obesity, and other metabolic diseases. It could also be used in the food, cosmetic, and biotechnology industries for the development of new glycosylation technologies. Limitations and Future Directions: While Ac4-GlcNAc is a valuable tool in glycoprotein research, the chemical synthesis of this compound is a complex multistep process. Additionally, many of the current studies of Ac4-GlcNAc in the glycoprotein field are still reliant on in vitro methods. There is a need for more in vivo studies to determine how this compound interacts with biological systems. Future research could also try and refine the synthesis process of this compound, allowing for more affordable production. CAS Number 69515-91-9 Product Name 1,3,4,6-Tetra-O-acetyl-2-deoxy-D-glucopyranose IUPAC Name [(2R,3S,4R)-3,4,6-triacetyloxyoxan-2-yl]methyl acetate Molecular Formula C14H20O9 Molecular Weight 332.3 g/mol InChI InChI=1S/C14H20O9/c1-7(15)19-6-12-14(22-10(4)18)11(20-8(2)16)5-13(23-12)21-9(3)17/h11-14H,5-6H2,1-4H3/t11-,12-,13?,14+/m1/s1 InChI Key KLEORKVJPIJWNG-VMXNZORSSA-N SMILES CC(=O)OCC1C(C(CC(O1)OC(=O)C)OC(=O)C)OC(=O)C Synonyms 2-Deoxy-D-arabino-hexopyranose 1,3,4,6-Tetraacetate; 1,3,4,6-Tetra-O-acetyl-2-deoxy-D-glucopyranose; 2-Deoxy-1,3,4,6-tetra-O-acetyl-D-glucopyranose Canonical SMILES CC(=O)OCC1C(C(CC(O1)OC(=O)C)OC(=O)C)OC(=O)C Isomeric SMILES CC(=O)OC[C@@H]1[C@H]([C@@H](CC(O1)OC(=O)C)OC(=O)C)OC(=O)C CAS No: 69515-91-9 Synonyms: 1,3,4,6-Tetra-O-acetyl-D-arabino-hexopyranose MDL No: MFCD09750746 Chemical Formula: C14H20O9 Molecular Weight: 332.3 References: 1. Reinhold U, Ugurel S, Tilgen W, Kadiata MM, et al., Oncology Rep. 2000, Sep-Oct, 7(5), p1093-7