67817-30-5, 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy- D-galactopyranose,
1,3,4,6-O-四乙酰基-2-叠氮-2-去氧- D-半乳糖,
CAS:67817-30-5
C14H19N3O9 / 373.32
MFCD01076182
1,3,4,6-O-四乙酰基-2-叠氮-2-去氧- D-半乳糖,
1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-a-D-galactopyranose is an azide sugar that is resistant to the activity of sulfide and can be used as a probe for sulfide in the distal colon. It has been shown that this sugar binds to recombinant human erythrocyte enzymes and inhibits their activities. The hydrolysis of this sugar by pancreatic enzymes has been shown to be dependent on the conformational state of the enzyme. This sugar also inhibits salivary amylase and intestinal sucrase activities.
1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-A-D-galactopyranose is a chemical compound that has gained significant attention among researchers and scientists due to its unique physical and chemical properties. The purpose of this paper is to provide an informative and engaging overview of the 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-A-D-galactopyranose compound. The paper will cover various aspects of this compound, including its definition and background, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity, and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations, and future directions.
Definition and Background:
1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-A-D-galactopyranose is a carbohydrate derivative that has four acetyl groups and four azido groups. It is a white crystalline powder that is soluble in water and has an empirical formula of C14H19N5O9. The compound is synthesized by acetylating 2,3,4,6-tetra-O-acetyl-D-galactopyranosyl azide in the presence of a strong acid catalyst.
Synthesis and Characterization:
The synthesis of 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-A-D-galactopyranose is achieved through the acetylation of 2,3,4,6-tetra-O-acetyl-D-galactopyranosyl azide in the presence of a strong acid catalyst, such as sulfuric acid or acetic anhydride. The reaction is carried out at room temperature, and the product is purified by recrystallization. The compound is characterized using various analytical techniques, including NMR spectroscopy, Fourier Transform Infrared Spectroscopy (FTIR), and High-Resolution Mass Spectrometry (HRMS).
Analytical Methods:
Various analytical methods are used to identify and quantify 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-A-D-galactopyranose. These include HPLC, Gas Chromatography-Mass Spectrometry (GC-MS), and High-Performance Thin-Layer Chromatography (HPTLC). These methods are useful for assessing the purity of the compound, detecting impurities, and determining the concentration of the compound in various samples.
Biological Properties:
1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-A-D-galactopyranose has several biological properties that make it useful in scientific experiments. It is a potent inhibitor of glycosylation, which is the process by which carbohydrates are attached to proteins and lipids. The compound has been shown to inhibit the replication of the influenza virus, HIV, and other viruses, making it a promising antiviral agent. Additionally, it has anticancer properties and can selectively target cancer cells.
Toxicity and Safety in Scientific Experiments:
Studies have shown that 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-A-D-galactopyranose has low toxicity and is safe for use in scientific experiments. However, it is essential to follow safety guidelines when handling the compound, as the azido and acetyl groups can be reactive and potentially hazardous.
Applications in Scientific Experiments:
1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-A-D-galactopyranose has several applications in scientific experiments. It is used as a glycosylation inhibitor in biological and medical research, as well as in the synthesis of complex carbohydrates. It is also utilized as a crosslinking agent in chemistry and material science research, and as an antiviral and anticancer agent in pharmacological research.
Current State of Research:
Research on 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-A-D-galactopyranose is ongoing, with several studies investigating its biological and chemical properties. Recently, researchers have focused on the synthesis of related compounds, as well as developing various techniques for using 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-A-D-galactopyranose as a chemical tool.
Potential Implications in Various Fields of Research and Industry:
The unique properties of 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-A-D-galactopyranose make it a promising compound with potential implications in various fields of research and industry. Its use as a glycosylation inhibitor has significant implications for understanding protein-carbohydrate interactions in biological systems. Additionally, its antiviral and anticancer properties make it a potential agent for developing new therapies for these diseases.
Limitations and Future Directions:
Despite its potential applications, 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-A-D-galactopyranose has several limitations. The compound is challenging to synthesize, and its reactive nature makes it challenging to handle and work with in laboratory settings. Future directions for the research on this compound include developing more efficient synthesis methods, exploring its use as a chemical tool, and investigating its potential applications in various fields of research and industry. Other possible future directions include exploring the use of related compounds and investigating the use of 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-A-D-galactopyranose in drug delivery systems and other biomedical applications.
Conclusion:
1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-A-D-galactopyranose is an exciting compound with unique properties and potential applications in various fields of research and industry. Its use as a glycosylation inhibitor and antiviral agent, as well as its anticancer properties, make it a promising agent for developing new therapies for various diseases. While there are limitations to the research on this compound, ongoing studies continue to explore its potential, and it will undoubtedly continue to be an area of interest for researchers and scientists.
CAS Number | 67817-30-5 |
Product Name | 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-A-D-galactopyranose |
IUPAC Name | [(2R,3R,4R,5R,6R)-3,4,6-triacetyloxy-5-azidooxan-2-yl]methyl acetate |
Molecular Formula | C14H19N3O9 |
Molecular Weight | 373.32 g/mol |
InChI | InChI=1S/C14H19N3O9/c1-6(18)22-5-10-12(23-7(2)19)13(24-8(3)20)11(16-17-15)14(26-10)25-9(4)21/h10-14H,5H2,1-4H3/t10-,11-,12+,13-,14+/m1/s1 |
InChI Key | QKGHBQJLEHAMKJ-RGDJUOJXSA-N |
SMILES | CC(=O)OCC1C(C(C(C(O1)OC(=O)C)N=[N+]=[N-])OC(=O)C)OC(=O)C |
Canonical SMILES | CC(=O)OCC1C(C(C(C(O1)OC(=O)C)N=[N+]=[N-])OC(=O)C)OC(=O)C |
Isomeric SMILES | CC(=O)OC[C@@H]1[C@@H]([C@@H]([C@H]([C@H](O1)OC(=O)C)N=[N+]=[N-])OC(=O)C)OC(=O)C |
CAS No: 67817-30-5 MDL No: MFCD01076182 Chemical Formula: C14H19N3O9 Molecular Weight: 373.32 |
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