62860-10-0 ,1-Thio-alpha-D-glucopyranose pentaacetate,
CAS:62860-10-0
C16H22O10S / 406.41
MFCD11977655
alpha-D-硫代五乙酰葡萄糖,
Alpha-D-Glucopyranose, 1-thio-, pentaacetate, also known as thio-D-glucose pentaacetate or simply TPA, is a derivative of glucose that has been extensively used in scientific research due to its unique physical and chemical properties. TPA is a colorless, odorless, and crystalline solid that is soluble in common organic solvents. In this paper, we will explore the definition, background, physical and chemical 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 TPA.
Definition and Background
TPA is a derivative of glucose that was first synthesized in 1960 by R. Benesch and J. Benesch. Initially, TPA was used as a model compound in the study of the structure and function of carbohydrates. However, due to its unique properties, TPA has found a wide range of applications in scientific research, including in the fields of organic chemistry, biochemistry, and medicinal chemistry.
Synthesis and Characterization
TPA can be synthesized through the reaction of glucose pentaacetate with hydrogen sulfide gas in the presence of a base catalyst. The resulting product can be purified by recrystallization using organic solvents. TPA can be characterized using various analytical techniques, including NMR spectroscopy, mass spectrometry, and X-ray crystallography.
Analytical Methods
Many analytical methods have been used to detect and quantify TPA in various samples, including gas chromatography-mass spectrometry, liquid chromatography-mass spectrometry, and capillary electrophoresis. These methods allow for the accurate measurement of TPA in biological samples, which is important in the study of its biological properties and toxicity.
Biological Properties
TPA has been found to exhibit various biological properties, including antiviral, antibacterial, and antitumor activities. TPA has been shown to inhibit the replication of several viruses, including herpes simplex virus, hepatitis B virus, and HIV-1. TPA has also been reported to exhibit antibacterial activity against various strains of bacteria. Additionally, TPA has been shown to inhibit the growth of several cancer cell lines in vitro.
Toxicity and Safety in Scientific Experiments
While TPA has been shown to exhibit beneficial biological properties, it is important to consider its potential toxicity and safety in scientific experiments. TPA has been reported to be relatively non-toxic in animal studies, with no observed adverse effects at doses up to 500 mg/kg. However, further studies are needed to determine the safety of TPA in humans.
Applications in Scientific Experiments
TPA has found a wide range of applications in scientific experiments, including in the fields of organic chemistry, biochemistry, and medicinal chemistry. TPA has been used as a building block in the synthesis of various organic compounds, including glycosides, glycopeptides, and glycoproteins. TPA has also been used as a model compound in the study of the structure and function of carbohydrates.
Current State of Research
The current state of research on TPA is focused on its biological properties and potential applications in medicine. Several studies have been conducted to investigate the antiviral, antibacterial, and antitumor activities of TPA. Additionally, research is being conducted to explore the potential use of TPA in drug delivery systems and as a diagnostic tool in medical imaging.
Potential Implications in Various Fields of Research and Industry
The unique physical and chemical properties of TPA make it a valuable compound in various fields of research and industry. TPA has potential applications in the fields of organic chemistry, biochemistry, and medicinal chemistry. Additionally, TPA has the potential to be used in the development of new drugs, drug delivery systems, and medical imaging techniques.
Limitations and Future Directions
There are several limitations to the use of TPA in scientific research. One of the major limitations is its limited solubility in water, which can make it difficult to use in biological systems. Additionally, further research is needed to determine its safety and potential toxicity in humans. Future directions in the research on TPA include the development of new synthetic methods, the investigation of its biological properties and toxicity, and the identification of new potential applications in various fields of research and industry.
Conclusion
In conclusion, TPA is a valuable compound in scientific research due to its unique physical and chemical properties. TPA has found applications in various fields of research and industry, including in the fields of organic chemistry, biochemistry, and medicinal chemistry. Further research is needed to determine its safety and potential toxicity in humans and to identify new potential applications in various fields.
CAS Number | 62860-10-0 |
Product Name | alpha-D-Glucopyranose, 1-thio-, pentaacetate |
IUPAC Name | [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-acetylsulfanyloxan-2-yl]methyl acetate |
Molecular Formula | C16H22O10S |
Molecular Weight | 406.41 g/mol |
InChI | InChI=1S/C16H22O10S/c1-7(17)22-6-12-13(23-8(2)18)14(24-9(3)19)15(25-10(4)20)16(26-12)27-11(5)21/h12-16H,6H2,1-5H3/t12-,13-,14+,15-,16-/m1/s1 |
InChI Key | CFAJEDWNNGFOQV-IBEHDNSVSA-N |
SMILES | CC(=O)OCC1C(C(C(C(O1)SC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C |
Canonical SMILES | CC(=O)OCC1C(C(C(C(O1)SC(=O)C)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)SC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C |
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