2, 3, 4, 6-Tetra-O-acetyl-b-D-mannopyranosylazide, CAS:65864-60-0

2,3,4,6-Tetra-O-acetyl-b-D-mannopyranosyl azide, commonly known as Ac4ManNAz, is a chemical compound with diverse potential applications in many fields of research and industry. This paper discusses the definition, 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 of Ac4ManNAz. Definition and Background: Ac4ManNAz is a modified sugar molecule derived from the natural sugar, mannose. It has four acetyl groups on the mannose molecule and an azide group at the C-6 position. The azide group is a reactive moiety that allows for the incorporation of Ac4ManNAz into glycan structures in vivo. In other words, Ac4ManNAz acts as a metabolic label that allows for selective labeling and visualization of glycoproteins and glycolipids in living cells and organisms. Synthesis and Characterization: Ac4ManNAz can be synthesized from commercially available D-mannose using a multi-step reaction scheme. The synthesis involves several protection and deprotection reactions to ensure the selective acetylation of the hydroxyl groups on the mannose molecule and the introduction of the azide group at the C-6 position. The final product is purified using column chromatography and characterized using nuclear magnetic resonance (NMR) spectroscopy, high-performance liquid chromatography (HPLC), and mass spectrometry (MS). Analytical Methods: The incorporation of Ac4ManNAz into glycoproteins and glycolipids can be detected using a range of analytical methods such as Western blotting, mass spectrometry, and fluorescence microscopy. These methods allow for the detection and visualization of labeled glycoconjugates in living cells and organisms. Biological Properties: Ac4ManNAz is biocompatible and does not interfere with normal cellular processes or growth. It has been shown to effectively label glycoproteins and glycolipids in various mammalian cell lines, as well as in mouse and zebrafish models. Ac4ManNAz has also been incorporated into bacterial and fungal cell walls, allowing for the visualization of glycan structures in these organisms. Toxicity and Safety in Scientific Experiments: Ac4ManNAz has been extensively tested for toxicity and safety in scientific experiments. It has been shown to be non-cytotoxic and does not induce cell death or apoptosis. However, like all azides, Ac4ManNAz is potentially explosive and should be handled with care. It is recommended that researchers working with Ac4ManNAz familiarize themselves with safe handling procedures and perform risk assessments before starting experiments. Applications in Scientific Experiments: Ac4ManNAz has numerous applications in scientific experiments, including glycoprotein and glycolipid labeling, imaging, and isolation. It has been used in studies to investigate the dynamics of protein glycosylation, as well as to identify and isolate glycoproteins from complex samples such as serum and cell lysates. Ac4ManNAz has also been used to study the glycan structures of pathogens, allowing for the identification of potential targets for drug development. Current State of Research: Ac4ManNAz is a well-established tool in the field of glycobiology, and its use has been increasing in many other fields of research. Recent studies have explored its applications in neuroscience, cancer research, and infectious diseases. Ac4ManNAz has also been used in the development of new therapeutic strategies, including cancer immunotherapy and targeted drug delivery. Potential Implications in Various Fields of Research and Industry: The potential applications of Ac4ManNAz are far-reaching and diverse. In the field of biotechnology, Ac4ManNAz can be used for the development of novel biomaterials, biosensors, and vaccines. It has potential applications in the food and agricultural industries, where it can be used for the detection and identification of pathogens and the improvement of crop yields. Ac4ManNAz also has implications for drug discovery and development, particularly in the identification of new drug targets and the development of more effective and specific therapies. Limitations and Future Directions: Despite the numerous advantages of Ac4ManNAz, there are limitations to its use. The incorporation of Ac4ManNAz into glycan structures is not 100% efficient, and the labeling of some glycoproteins may be missed. Future research should focus on improving the efficiency and selectivity of Ac4ManNAz labeling. Additionally, research is needed to explore the potential use of Ac4ManNAz in in vivo imaging and therapy. Finally, further studies are needed to investigate the effects of Ac4ManNAz on cellular processes and signaling pathways, particularly in disease states. Conclusion: Ac4ManNAz is a valuable tool in many areas of research and industry, with potential applications in biotechnology, medicine, and agriculture. Its unique properties make it an indispensable tool in the study of glycobiology and the identification of new targets for drug development. Further research is needed to explore the full potential of Ac4ManNAz and its implications for various fields of research and industry. CAS Number 65864-60-0 Product Name 2,3,4,6-Tetra-O-acetyl-b-D-mannopyranosyl azide IUPAC Name [(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-azidooxan-2-yl]methyl acetate Molecular Formula C14H19N3O9 Molecular Weight 373.32 g/mol InChI InChI=1S/C14H19N3O9/c1-6(18)22-5-10-11(23-7(2)19)12(24-8(3)20)13(25-9(4)21)14(26-10)16-17-15/h10-14H,5H2,1-4H3/t10-,11-,12+,13+,14-/m1/s1 InChI Key NHNYHKRWHCWHAJ-PEBLQZBPSA-N SMILES CC(=O)OCC1C(C(C(C(O1)N=[N+]=[N-])OC(=O)C)OC(=O)C)OC(=O)C Canonical SMILES CC(=O)OCC1C(C(C(C(O1)N=[N+]=[N-])OC(=O)C)OC(=O)C)OC(=O)C Isomeric SMILES CC(=O)OC[C@@H]1[C@H]([C@@H]([C@@H]([C@@H](O1)N=[N+]=[N-])OC(=O)C)OC(=O)C)OC(=O)C CAS No: 65864-60-0 Synonyms: b-D-Mannopyranosyl azide tetraacetate MDL No: MFCD08703928 Chemical Formula: C14H19N3O9 Molecular Weight: 373.32