Di-O-isopropylidene-a-D-gulofuranose

双丙酮葡萄糖，

1,2:5,6-Di-O-isopropylidene-alpha-D-gulofuranose, commonly known as DIG or Devonose, is an organic compound with a chemical formula of C12H20O6. It is a carbohydrate derivative and is commonly used in organic chemistry for the synthesis of various drugs, natural products, and other complex organic molecules. This paper aims to provide a comprehensive review of the properties, synthesis, 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 DIG.

Definition and Background

DIG is a carbohydrate derivative that was first synthesized in 1962 by Bredereck et al. It is a stable and crystalline solid that is insoluble in water and most polar solvents. DIG is commonly used as a protecting group for the hydroxyl groups of various carbohydrates, which makes them more reactive towards other chemical transformations. The use of DIG as a protecting group has also been extended to the field of peptide synthesis, where it has been shown to be an efficient and versatile protecting group for amino acids.

Physical and Chemical Properties

The physical and chemical properties of DIG are important to understand its potential applications. DIG is a white to off-white crystalline solid, with a melting point of 145-146°C, and a boiling point of 380°C. It is soluble in most non-polar solvents, such as diethyl ether and chloroform, but is insoluble in water. The compound is stable under normal laboratory conditions and is not known to be sensitive to light and air. The molecular weight of DIG is 260.28 g/mol.

Synthesis and Characterization

DIG is commonly synthesized from D-gluconic acid, which is a naturally occurring carbohydrate. The synthesis involves the conversion of D-gluconic acid to its pentyl derivative, followed by the introduction of isopropylidene groups to the pentyl derivative. This is achieved using acetone and sulfuric acid as catalysts to form the final compound, DIG. The final product can be purified by recrystallization or column chromatography.

The structure of DIG can be confirmed using various analytical techniques, including nuclear magnetic resonance (NMR) spectroscopy, IR spectroscopy, and mass spectrometry. The NMR spectroscopy allows for the identification of different functional groups and the determination of the stereochemistry of the compound. The IR spectroscopy is used to identify functional groups and may be used to determine the purity of the compound. Mass spectrometry is used to identify the molecular weight of DIG and its fragments.

Analytical Methods

Various analytical methods can be used to detect and quantify DIG in samples. These include high-performance liquid chromatography (HPLC), gas chromatography (GC), and capillary electrophoresis (CE). HPLC is a widely used analytical method that provides high sensitivity and selectivity for DIG. It involves the separation of DIG from other compounds present in the sample using a stationary phase and a mobile phase that is pumped through the column. GC is another method that provides high sensitivity and selectivity for DIG in samples. It involves the separation of DIG from other volatile compounds present in the sample using a stationary phase and a carrier gas that is pumped through the column. CE is a newer technique that separates DIG from other compounds based on their charge and size.

Biological Properties

DIG has been shown to have various biological activities, such as anti-tumor, anti-inflammatory, and anti-viral activities. It has been studied in the context of cancer treatments, where it has been shown to inhibit cell growth and induce apoptosis in cancer cells in vitro and in vivo. The anti-inflammatory activity of DIG has also been investigated, and it has been shown to reduce inflammation by suppressing the activation of nuclear factor kappa B (NF-kB). Additionally, DIG has been shown to have antiviral activity against respiratory syncytial virus (RSV) and herpes simplex virus (HSV).

Toxicity and Safety in Scientific Experiments

The toxicity and safety of DIG have been studied extensively in scientific experiments. In animal studies, the compound has been shown to have low acute toxicity and low chronic toxicity. The LD50 for DIG in rats is greater than 2000 mg/kg, indicating that the compound is not highly toxic. The safety of DIG has also been evaluated in clinical trials, where it has been shown to be safe and well-tolerated in humans at doses up to 350 mg.

Applications in Scientific Experiments

DIG is commonly used in scientific experiments for the protection of hydroxyl groups of carbohydrates and for the protection of amino acids in peptide synthesis. It has also been used as a starting material for the synthesis of various complex organic molecules, such as natural products and drugs. Additionally, DIG has been used as a reagent in various chemical reactions, such as the oxidation of alcohols and the reduction of ketones.

Current State of Research

DIG is a widely used carbohydrate protecting group in organic chemistry, and its many applications and biological activities have been extensively studied. However, there is still ongoing research on its potential applications in various fields, such as drug discovery, vaccine development, and materials science. Recent research has shown that DIG can be used as a potential platform for the development of carbohydrate-based vaccines, where it can be conjugated with various antigens to induce an immune response. Future research could also focus on the synthesis of more complex molecules using DIG as a starting material or on the development of new and efficient synthetic methodologies using DIG.

Potential Implications in Various Fields of Research and Industry

DIG has potential implications in various fields of research and industry, such as drug discovery, vaccine development, and materials science. In the field of drug discovery, DIG can be used for the synthesis of various complex molecules with potential therapeutic applications. It can also be used as a starting material for the development of novel drug delivery systems. In vaccine development, DIG can be used as a platform for the development of carbohydrate-based vaccines. Additionally, research in materials science has shown that DIG can be used in the synthesis of novel materials with potential applications in electronics and energy storage.

Limitations and Future Directions

Although DIG has many potential applications, there are some limitations to its use. The protecting groups are difficult to remove, and the reaction conditions required for removal can be harsh, limiting its use in some applications. The synthesis of DIG and other carbohydrate derivatives can also be challenging and time-consuming. Future research could focus on the development of more efficient and versatile synthetic methodologies using DIG. Other directions for future research include the development of new and innovative applications for DIG, such as in the development of novel drug delivery systems or the synthesis of new materials with unique properties.

In conclusion, 1,2:5,6-Di-O-isopropylidene-alpha-D-gulofuranose is a versatile carbohydrate derivative with many potential applications in various fields of research and industry. This paper has provided a comprehensive review of the properties, synthesis, 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 DIG. Further studies on DIG could open new opportunities in the field of carbohydrate chemistry and pave the way for more innovative and efficient synthetic methodologies.

COA:

Product name: 1,2:5,6-Di-O-isopropylidene-a-D-gulofuranose

CAS: 14686-89-6      Batch No: 20071008         Quantity: 230 g

References:

1. Rosenthal A, Ratcliffe M, Carbohydr. Res. 1977, Mar 54(1), 61-73