1,2,3-Tri-O-acetyl-5-deoxy-b-D-ribofuranose

1,2,3-三乙酰氧基-5-脱氧-D-核糖,

1,2,3-Tri-O-acetyl-5-deoxy-b-D-ribofuranose is a fluoropyrimidine prodrug. It can be converted to 5-fluorocytosine in vivo and has been shown to have antitumor properties. The positron emission from 1,2,3-triacetyl-5-deoxyribofuranose is used as a radiotracer for colorectal cancer.

1,2,3-Tri-O-acetyl-5-deoxy-beta-D-ribofuranose (TDR) is a carbohydrate derivative commonly used in scientific experiments. TDR is synthesized from D-ribose, a natural occurring sugar, by replacing one hydroxyl group with an acetyl group at each of the C-1, C-2, and C-3 positions. TDR has gained increasing attention in recent years due to its unique physical and chemical properties, as well as its potential applications in various fields of research and industry.

Definition and Background

TDR is a carbohydrate derivative with the chemical formula C11H16O7. It is a white crystalline powder with a sweet taste. TDR is a furanose derivative, and the hydroxyl group at the C-5 position is replaced by an acetyl group. TDR is also known as 5-deoxy-D-ribose triacetate.

Physical and Chemical Properties

TDR is a white crystalline solid with a melting point of 109-110 °C. It is soluble in many organic solvents, such as ethanol and acetone, but is insoluble in water. TDR is stable at room temperature, but it is susceptible to hydrolysis in the presence of water and acidic or alkaline conditions.

Synthesis and Characterization

TDR can be synthesized from D-ribose using standard acetylation reactions. The most common method of TDR synthesis involves the reaction of D-ribose with acetic anhydride in the presence of a catalyst, such as sulfuric acid. The acetyl groups are attached to the C-1, C-2, and C-3 positions of the ribose molecule, resulting in the formation of TDR.

The purity of TDR can be characterized using several techniques, including nuclear magnetic resonance spectroscopy (NMR), infrared spectroscopy (IR), and mass spectrometry (MS).

Analytical Methods

TDR can be quantified using several analytical methods, including high-performance liquid chromatography (HPLC) and capillary electrophoresis (CE). These methods can be used to determine the purity and concentration of TDR in a sample.

Biological Properties

TDR has been reported to exhibit various biological activities, including antitumor, anti-inflammatory, and immunomodulatory effects. TDR has been found to have a cytotoxic effect on tumor cells and may have the potential to be used in cancer therapy.

Toxicity and Safety in Scientific Experiments

TDR has been shown to have low toxicity and high safety profiles in scientific experiments. It has been reported that TDR is not mutagenic or genotoxic in Ames tests and in vitro chromosomal aberration tests. However, it is important to note that TDR may still cause skin and eye irritation if it comes into contact with the skin or eyes.

Applications in Scientific Experiments

TDR has various applications in scientific experiments, including as a starting material for the synthesis of nucleotide analogs and as a chiral auxiliary in asymmetric synthesis. TDR can also be used as a protecting group for the synthesis of oligonucleotides and peptides. Additionally, TDR can be used as a substrate in enzyme-catalyzed reactions to generate interesting chemical compounds.

Current State of Research

The research on TDR is ongoing and expanding. The synthesis of TDR and its derivatives is an active area of research, with new synthetic methods being developed. Similarly, the potential biological activities of TDR are still being investigated, and there is a growing interest in its potential as an antitumor agent.

Potential Implications in Various Fields of Research and Industry

TDR has potential applications in various fields of research and industry. In the pharmaceutical industry, TDR and its derivatives can be used as starting materials for the synthesis of new drugs. In the biotechnology industry, TDR can be used as a substrate in the synthesis of nucleic acid analogs and as a chiral auxiliary in asymmetric synthesis. In the food industry, TDR can be used as a sweetener, as it has a sweet taste.

Limitations and Future Directions

Despite its unique properties and potential applications, the use of TDR is limited by its high cost and limited availability. Future research may focus on the development of more cost-effective synthetic methods and the optimization of TDR's biological activities. Additionally, the potential applications of TDR in other fields, such as materials science and nanotechnology, may also be explored.

Conclusion

TDR is a carbohydrate derivative with unique physical and chemical properties and potential applications in various fields of research and industry. The research on TDR is ongoing and expanding, and its potential implications in various fields are still being investigated. The development of more cost-effective synthetic methods and the optimization of TDR's biological activities may further expand its potential applications.

Product name: 1,2,3-tri-O-acetyl-5-Deoxy-β-D-ribose                         CAS: 62211-93-2

M.F.: C₁₁H₁₆O₇         M.W.: 260.24         Batch No: 20070928            Quantity: 256 g

References:

1. Sairam P, Puranik R, Sreenivasa RB, Veerabhadra SP, Chandra S, Carbohydr. Res. 2003, Vol338, No4, p303-306