84278-00-2, 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:84278-00-2
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-D-galactopyranose is a carbohydrate that has been shown to bind to the lectin domain of the human insulin receptor. This binding is thought to modulate the activity of this protein. The carbohydrate has also been shown to inhibit the uptake of galactose by pancreatic beta cells in vitro. 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose is postulated to have anti cancer properties and may be used as a blocker for tumor growth.
1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose (TAG) is a chemical compound widely used in scientific experiments and research. It is a derivative of galactose, an important biological molecule found in many living organisms. TAG has a unique chemical structure and exhibits interesting physical and chemical properties, making it a valuable tool in various scientific fields.
Definition and Background
TAG belongs to the class of azido-sugars, which are sugars that have undergone a chemical modification by the addition of an azide group (-N3) to their structure. Azido-sugars have gained importance due to their ability to react selectively with biomolecules, such as proteins and nucleic acids, allowing for their labeling and tracking in living systems. TAG was first synthesized in the 1980s and has since been extensively studied for its biological and chemical applications.
Synthesis and Characterization
TAG can be synthesized from commercially available starting materials using a multistep chemical reaction. The most common method involves the acetylation of galactose to form the intermediate product, 2,3,4,6-tetra-O-acetyl-D-galactosyl chloride, which is then reacted with sodium azide to give TAG. Characterization of TAG is usually done using analytical techniques, such as nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, and mass spectrometry (MS).
Analytical Methods
TAG can be detected and quantified using a variety of analytical techniques, including high-performance liquid chromatography (HPLC), capillary electrophoresis, and fluorescence spectroscopy. These methods allow for the accurate determination of TAG concentration and its interactions with other molecules.
Biological Properties
TAG has been extensively studied for its biological properties, particularly its ability to serve as a substrate for glycosyltransferases, which are enzymes that catalyze the transfer of sugar molecules in living systems. TAG can be used to modify biomolecules, such as proteins and lipids, to study their interactions and functions in biological processes. TAG has also been shown to have an inhibitory effect on certain viral infections, making it a potential antiviral agent.
Toxicity and Safety in Scientific Experiments
TAG has a low acute toxicity and is considered to be relatively safe for scientific experiments. However, care should be taken when handling TAG due to its potential decomposition and the release of toxic nitrogen gas. Proper safety precautions, such as the use of fume hoods and protective equipment, should always be used when working with TAG.
Applications in Scientific Experiments
TAG has various applications in scientific experiments, including:
- The labeling and tracking of biomolecules in living systems using selective chemical reactions.
- The modification of biomolecules for studying their function and interactions.
- The inhibition of certain viral infections, making it a potential antiviral agent.
- The synthesis of other azido-sugars and sugar-based compounds for various chemical and biological applications.
Current State of Research
TAG continues to be an active area of research, with ongoing studies focusing on its various applications and properties. Recent research has explored the use of TAG in the development of new antiviral agents and in the study of protein glycosylation in living systems.
Potential Implications in Various Fields of Research and Industry
TAG has potential implications in various fields of research and industry, including:
- Biotechnology: TAG can be used in the development of new diagnostic tools and therapeutics for various diseases.
- Pharmacology: TAG has been shown to have antiviral properties, making it a potential drug candidate for the treatment of viral infections.
- Materials Science: TAG can be used in the synthesis of new materials with unique physical and chemical properties.
- Chemical Synthesis: TAG can be used in the synthesis of other azido-sugars and sugar-based compounds with different properties and applications.
Limitations and Future Directions
TAG has limitations in terms of its use and application, including its potential toxicity and instability. Future research should focus on developing new synthetic routes and improving the stability and safety of TAG. Other future directions include expanding the use of TAG in different fields and exploring its potential applications in medical and industrial settings.
Conclusion
TAG is a unique and valuable chemical compound that has found various applications in scientific experiments and research. Its physical and chemical properties, as well as its biological effects, make it a valuable tool in many areas of research. While there are limitations to its use, ongoing research is exploring new synthetic routes and applications, making TAG a promising candidate for various fields and industries.
CAS Number | 84278-00-2 |
Product Name | 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose |
IUPAC Name | [(2R,3R,4R,5R)-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-RQICVUQASA-N |
SMILES | CC(=O)OCC1C(C(C(C(O1)OC(=O)C)N=[N+]=[N-])OC(=O)C)OC(=O)C |
Synonyms | 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose; 2-Azido-2-deoxy-D-galactopyranose 1,3,4,6-Tetraacetate; |
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(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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