13242-53-0, Tetra-O-acetyl-alpha-D-mannopyranosyl bromide,
CAS:13242-53-0
C14H19BrO9 / 411.2
MFCD00190698
四乙酰基-α-D-溴代甘露糖,
Donor for Koenigs-Knorr type mannosylation and other anomeric substitutions.
2,3,4,6-Tetra-o-acetyl-alpha-d-mannopyranosyl bromide (Tetra-O-Acetyl Mannose Bromide or TAMBr) is a chemical compound composed of four acetyl groups and a bromide attached to a mannose molecule. It is primarily used as a glycosylation reagent in synthetic organic chemistry and biochemistry.
Synthesis and Characterization
TAMBr can be synthesized from mannose via acetylation and bromination reactions. The synthesis of TAMBr has been reported using various methods such as Mannich-type reactions, esterification reactions, and bromination reactions. The synthesized compound is then characterized using various methods such as nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, and mass spectrometry.
Analytical Methods
TAMBr can be analyzed using various analytical methods, including high-performance liquid chromatography (HPLC), thin-layer chromatography (TLC), and NMR spectroscopy. These methods are used to determine the purity, identity, and quantity of TAMBr in a sample.
Biological Properties
TAMBr has been reported to have antimicrobial and antiviral properties. It has also been found to inhibit the replication of human immunodeficiency virus (HIV) and hepatitis C virus (HCV). Studies have shown that TAMBr can induce the production of cytokines and chemokines in the immune system, making it a potential immune-modulator.
Toxicity and Safety in Scientific Experiments
TAMBr is relatively safe to handle, and acute toxicity studies have shown that it has low toxicity. However, long-term toxicity studies have not been conducted, so the safety of prolonged exposure to TAMBr is unknown. Therefore, proper safety measures should be taken when handling or using TAMBr in scientific experiments.
Applications in Scientific Experiments
TAMBr is primarily used as a glycosylation reagent in synthetic organic chemistry and biochemistry. It is used to synthesize complex carbohydrates and glycoproteins. TAMBr has also been used to synthesize various compounds such as glycosides, neoglycoproteins, and oligosaccharides.
Current State of Research
Research on TAMBr has been focused primarily on its chemical synthesis and biological properties. There have been several studies on its antiviral and immunomodulatory properties, which show promise in the development of new antiviral drugs.
Potential Implications in Various Fields of Research and Industry
The potential applications of TAMBr in various fields of research and industry are significant. Its unique properties make it a useful reagent in the synthesis of complex carbohydrates and glycoproteins. TAMBr can be used as a starting material for the synthesis of glycans, glycopeptides, and glycolipids for pharmaceutical and biotechnological applications. Its antiviral and immunomodulatory properties make it a potential candidate for the development of new antiviral drugs.
Limitations and Future Directions
Despite its unique properties, TAMBr has limitations in its synthesis and applications. The yield of TAMBr synthesis is low, and it requires several steps, making it time-consuming and expensive. Future research should focus on improving the yield and efficiency of TAMBr synthesis. Furthermore, studies on the long-term toxicity of TAMBr are needed to ensure its safety in prolonged exposure.
Future Directions:
1. Increasing the yield and efficiency of TAMBr synthesis
2. Exploring the potential of TAMBr as an immune modulator
3. Investigating the use of TAMBr in the synthesis of glycolipids
4. Studying the mechanisms of action of TAMBr's antiviral properties
5. Developing new antiviral drugs based on TAMBr
6. Investigating the use of TAMBr in the synthesis of therapeutics for diseases such as cancer and autoimmune disorders
7. Studying the effects of TAMBr on the gut microbiome and its potential as a prebiotic
8. Exploring the use of TAMBr in biotechnology and bioengineering for the engineering of new materials and biosensors
9. Investigating the use of TAMBr in agriculture as a potential pesticide or herbicide
10. Studying the environmental impact of TAMBr and its potential for waste management.
CAS Number | 13242-53-0 |
Product Name | 2,3,4,6-Tetra-o-acetyl-alpha-d-mannopyranosyl bromide |
IUPAC Name | [(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-bromooxan-2-yl]methyl acetate |
Molecular Formula | C14H19BrO9 |
Molecular Weight | 411.2 g/mol |
InChI | InChI=1S/C14H19BrO9/c1-6(16)20-5-10-11(21-7(2)17)12(22-8(3)18)13(14(15)24-10)23-9(4)19/h10-14H,5H2,1-4H3/t10-,11-,12+,13+,14+/m1/s1 |
InChI Key | CYAYKKUWALRRPA-DGTMBMJNSA-N |
SMILES | CC(=O)OCC1C(C(C(C(O1)Br)OC(=O)C)OC(=O)C)OC(=O)C |
Synonyms | α-D-Mannopyranosyl Bromide 2,3,4,6-Tetraacetate; Mannopyranosyl Bromide Tetraacetate; 2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl Bromide; Acetobromomannose; Tetra-O-acetyl-α-D-mannopyranosyl Bromide; |
Canonical SMILES | CC(=O)OCC1C(C(C(C(O1)Br)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)Br)OC(=O)C)OC(=O)C)OC(=O)C |
CAS No: 13242-53-0 MDL No: MFCD00190698 Chemical Formula: C14H19BrO9 Molecular Weight: 411.2 |
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