53784-29-5,2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl azide,
Cas:53784-29-5
MFCD05664724
C14H19N3O9 / 373.32
,2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl azide,
2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl azide, commonly known as TAMPA, is a chemical compound that has attracted much attention in the scientific research and industry fields. It is a derivative of alpha-D-Mannopyranose, a six-carbon sugar that is widely found in plant and fungal polysaccharides. TAMPA has been recognized as a versatile biochemical building block, particularly in the field of glycoscience, due to its unique physicochemical properties and biological functions.
Definition and Background
TAMPA is a white to off-white crystalline powder that is water-insoluble but soluble in most organic solvents such as chloroform, acetone, and ethanol. It is a glycosyl azide that contains four acetyl groups attached to the hydroxyl groups of the sugar molecule. TAMPA is extensively used as a reagent for chemical synthesis of glycoconjugates, which are biomolecules that have a carbohydrate unit attached to a protein or lipid molecule.
Synthesis and Characterization
TAMPA can be synthesized through various chemical methods, including acidic catalysis, base-catalyzed deacetylation, and one-pot synthesis from mannose derivatives. These methods have been extensively studied, and their pros and cons have been compared in terms of yield, purity, and applicability. Characterization of TAMPA can be achieved using various spectroscopic and chromatographic methods, such as nuclear magnetic resonance (NMR) spectroscopy, high-performance liquid chromatography (HPLC), and mass spectrometry (MS).
Analytical Methods
Analytical methods are crucial for the detection and quantification of TAMPA and its derivatives. Commonly used methods include HPLC, in which the separation of TAMPA is achieved by chromatographic techniques, and NMR spectroscopy, which provides information on the molecular structure of TAMPA. Other methods, such as capillary electrophoresis and fluorescence-based assays, have been developed to increase the sensitivity and specificity of detection.
Biological Properties
TAMPA has been shown to exhibit various biological activities, such as antiviral, antitumor, and immunomodulatory effects. TAMPA and its derivatives have been extensively studied in the field of immunology, particularly in the modulation of T cell responses. Studies have demonstrated that TAMPA can promote antigen-specific T cell activation and proliferation, which can be used to develop new immunotherapeutic agents.
Toxicity and Safety in Scientific Experiments
Studies have shown that TAMPA exhibits low toxicity when used at moderate concentrations, and its side effects are generally mild and reversible. However, the safety of TAMPA and its derivatives in humans has not been thoroughly investigated, and caution should be exercised when handling and using these compounds in scientific experiments.
Applications in Scientific Experiments
TAMPA has various applications in scientific experiments, such as the synthesis of glycoproteins, glycolipids, and glycan arrays. It is also used in the development of new vaccines and immunotherapeutic agents. TAMPA has been shown to enhance the immunogenicity of antigens, and its combination with adjuvants has been studied in preclinical and clinical trials.
Current State of Research
Research on TAMPA and its derivatives is ongoing, and new applications and potential therapeutic targets are being explored. Studies are being conducted to investigate the role of TAMPA in various autoimmune diseases and cancer models. The use of TAMPA in the development of diagnostic tools and imaging agents is also being explored.
Potential Implications in Various Fields of Research and Industry
TAMPA has potential implications in various fields of research and industry, such as biotechnology, biopharmaceuticals, and nanotechnology. It can be used in the synthesis of new therapeutic agents, diagnostic tools, and biomaterials. TAMPA and its derivatives can also be used as probes to study biological processes and as tools to engineer new biological systems.
Limitations and Future Directions
Although TAMPA has many potential applications, there are still limitations that need to be addressed. One limitation is its low water solubility, which can limit its use in certain applications. Future research should focus on developing new derivatives with improved solubility and stability. Other limitations include the lack of precise mechanistic understanding of TAMPA's biological effects and its toxicity in vivo. New research should aim to address these issues and expand our knowledge on the therapeutic potential of TAMPA.
List of Future Directions:
1. Development of new derivatives with improved physicochemical and biological properties.
2. Investigation of the effect of TAMPA and its derivatives on the modulation of immune responses.
3. Use of TAMPA as a tool for the study of host-microbe interactions and the development of new antimicrobial agents.
4. Development of TAMPA-based diagnostic tools and imaging agents for the detection of cancer and other diseases.
5. Integration of TAMPA with other technologies such as nanotechnology and biopharmaceuticals for the development of new therapeutic agents and biomaterials.
6. Study of the potential use of TAMPA in gene delivery and regenerative medicine.
7. Exploration of the safety and toxicity of TAMPA and its derivatives in vivo.
8. Investigation of the mechanism of action of TAMPA and its derivatives in different biological systems.
9. Use of TAMPA for the development of new vaccines and immunotherapeutic agents.
10. Implementation of TAMPA in industrial applications, such as the production of synthetic biopolymers and biomolecules.
CAS Number | 53784-29-5 |
Product Name | 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl azide |
IUPAC Name | [(2R,3R,4S,5S,6S)-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-DGTMBMJNSA-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 |
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