56883-33-1 ,1,3,4,6-Tetra-O-Acetyl-2-Azido-2-Deoxy- D-glucopyranose,
1,3,4,6-O-四乙酰基-2-叠氮-2-去氧-D-葡萄糖,
CAS:56883-33-1
C14H19N3O9 / 373.32
MFCD01076183
1,3,4,6-O-四乙酰基-2-叠氮-2-去氧-D-葡萄糖,
1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-alpha-D-glucopyranose (TAAG) is a chemical compound used extensively in scientific research. This paper aims to provide an overview of TAAG, including its properties, synthesis, characterization, analytical methods, biological properties, toxicity, safety, and applications in scientific experiments. It will also analyze the current state of research, potential implications in various fields of research and industry, and limitations and future directions.
Definition and Background
TAAG is a sugar derivative that contains azide functionality. It finds application in glycan engineering, bioorthogonal labeling, and antibiotic development. It is often used as a precursor to produce various azidosugars.
Synthesis and Characterization
TAAG can be synthesized through a multi-step process involving acetylation, azidation, and deacetylation. The synthesized TAAG can then be characterized by various techniques such as nuclear magnetic resonance (NMR) spectroscopy, X-ray crystallography, and mass spectrometry.
Analytical Methods
The analytical methods used for TAAG analysis include Thin-Layer Chromatography (TLC), High-Performance Liquid Chromatography (HPLC), and Gas Chromatography (GC). These methods are used to confirm the purity, identity, and concentration of TAAG.
Biological Properties
TAAG exhibits antimicrobial properties against various Gram-positive and Gram-negative bacteria. It also promotes efficient glycoprotein labeling and visualization of glycans in living cells. Moreover, it has been used to create a click chemistry technique, which aids in the visualization of glycan synthesis.
Toxicity and Safety in Scientific Experiments
The effects of TAAG on human health are not yet fully understood. However, TAAG has been reported to have low toxicity levels, and this makes it suitable for use in scientific experiments.
Applications in Scientific Experiments
TAAG finds its application in various scientific fields, including bioorthogonal chemistry, glycoprotein labeling, and antibiotic development. It is also used in click chemistry, which improves the imaging of biological processes.
Current State of Research
The current research on TAAG is aimed at identifying new applications, improving synthesis protocols, and enhancing its efficacy for use in various scientific fields. Research is also being conducted to understand the molecular mechanism underlying the biological activity of TAAG.
Potential Implications in Various Fields of Research and Industry
TAAG presents various implications for research and industry, including the development of new antibiotics, better understanding of biological processes, glycoproteomics, and metabolic engineering.
Limitations and Future Directions
The limitations of TAAG include its low solubility in water, which limits its application in aqueous media. Additionally, the high cost of synthesis limits its use in large-scale industrial applications, and more research is needed to optimize the synthesis process. Future directions include improving the solubility of TAAG, optimizing its synthesis, and exploring new applications in biotechnology, glycobiology, and drug discovery.
Conclusion
TAAG is a crucial compound in scientific research, with various applications in bioorthogonal labeling, drug discovery, and other fields. Its physical and chemical properties, synthesis, and analytical methods are essential in understanding its behavior and uses in scientific experiments. The current research on TAAG aims to enhance its efficacy and optimize its synthesis for use in various fields. Finally, exploring new applications of TAAG and addressing its limitations will further improve its potential contributions to scientific research and industry.
CAS Number | 56883-33-1 |
Product Name | 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-alpha-D-glucopyranose |
IUPAC Name | [(2R,3S,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-KSTCHIGDSA-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: 56883-33-1 MDL No: MFCD01076183 Chemical Formula: C14H19N3O9 Molecular Weight: 373.32 |
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