1,3,5-Tri-O-benzoyl-a-D-ribofuranose

1,3,5-三苯甲酰基-D-呋喃核糖,

1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose is a derivative of ribofuranose, a five-carbon sugar that plays vital biological roles in DNA, RNA, and ATP metabolic pathways. Ribofuranose derivatives like 1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose have attracted research interest due to their biological properties and potential applications in various fields, including drug discovery, synthetic biology, and materials science. This paper provides an overview of the definition, properties, synthesis, analytical methods, applications, future directions, and limitations of 1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose.

Synthesis and Characterization

The synthesis of 1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose involves the protection of the hydroxyl groups of ribofuranose with benzoyl groups using benzoyl chloride and pyridine. The benzoylation occurs selectively at positions 1, 3, and 5 of the ribofuranose ring, yielding 1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose. The product is purified by column chromatography or recrystallization from a suitable organic solvent.

The characterization of 1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose is typically performed using various techniques, including NMR spectroscopy, mass spectrometry, and X-ray crystallography. The NMR spectra of 1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose show characteristic signals corresponding to its ribofuranose core and benzoyl groups. The mass spectrometry data confirm the molecular weight of the compound, and X-ray crystallography provides information about its crystal structure.

Analytical Methods

The analytical methods for 1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose include UV-Vis spectroscopy, HPLC, and TLC. UV-Vis spectroscopy is useful for determining the purity and concentration of 1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose based on its absorption maximum at 244 nm. HPLC and TLC are used for the separation and identification of 1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose in complex mixtures.

Biological Properties

The biological properties of 1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose are under investigation due to its potential as an activator of human adenosine monophosphate-activated protein kinase (AMPK), a key regulator of cellular energy homeostasis. Recent studies have shown that 1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose can activate AMPK in vitro and in vivo, suggesting its potential as a therapeutic agent for metabolic disorders such as obesity, diabetes, and cancer.

Toxicity and Safety in Scientific Experiments

The toxicity and safety profile of 1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose have not been extensively studied. However, it is recommended to handle the compound with proper protective gear and follow standard safety protocols for handling organic chemicals.

Applications in Scientific Experiments

1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose has several applications in scientific experiments, such as:

1. As a precursor for the synthesis of ribofuranose-based ligands and receptors for biological sensing and imaging.

2. As a modulator of AMPK activity for investigating its role in cellular signaling pathways and metabolic diseases.

3. As a starting material for the synthesis of ribofuranose analogs with altered biological activities.

Current State of Research

The recent research on 1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose has focused on its synthesis, characterization, and biological activities. Several synthetic routes have been reported for the preparation of 1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose, including highly efficient and scalable procedures. The biological properties of 1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose are being studied for its role in cellular metabolism, energy homeostasis, and disease development.

Potential Implications in Various Fields of Research and Industry

The potential implications of 1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose in various fields of research and industry are:

1. In drug discovery, 1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose may serve as a lead compound for developing AMPK activators with therapeutic potential for metabolic disorders.

2. In synthetic biology, 1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose can be used as a building block for designing artificial ribofuranose-based molecular machines and sensors.

3. In materials science, 1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose may serve as a template for the synthesis of ribofuranose-based nanomaterials with tailored properties.

Limitations and Future Directions

The limitations and future directions of 1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose research are:

1. The toxicity and safety profile of 1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose need to be systematically evaluated.

2. The relationship between the chemical structure of 1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose and its biological activities warrants further investigation.

3. The synthetic routes for preparing 1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose need to be optimized for higher efficiency, yield, and scalability.

4. The potential applications of 1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose in various fields need to be explored further, such as in drug delivery, materials science, and bioengineering.

Conclusion

1,3,5-Tri-O-benzoyl-alpha-d-ribofuranose is a ribofuranose derivative that has attracted research interest due to its biological activities and potential applications in various fields. Its synthesis, characterization, and analytical methods have been studied extensively, and its biological activities have shown therapeutic potential for metabolic disorders. Future research directions focus on evaluating its toxicity and safety, optimizing its synthetic routes, and exploring its potential applications in drug discovery, synthetic biology, and materials science.

COA:

Product name: 1,3,5-Tri-O-benzoyl-D-ribofuranose        CAS: 22224-41-5

M.F.: C₂₆H₂₂O₈    M.W._: 462.45   Batch No: 20120510   Quantity: 1.6 kg

References:

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