1,2:4,5-Di-O-isopropylidene-b-D-fructopyranose

双丙酮-D-果糖, 双异丙叉-D-果糖,

1,2:4,5-Di-O-isopropylidene-beta-D-fructopyranose, also known as DFIP, is a stable derivative of fructose. It is a carbohydrate that is commonly used in organic synthesis. This compound is also used as a precursor or intermediate in the production of glycosyl donors, which are used for glycosylation.

The derivation of 1,2:4,5-Di-O-isopropylidene-beta-D-fructopyranose was first reported in the early 1940s. It was synthesized by the reaction of fructose with acetone to form diacetonide, followed by treatment with isopropylmagnesium bromide. This reaction leads to the formation of a stable and crystalline derivative, which was identified as DFIP.

Synthesis and Characterization

The synthesis of 1,2:4,5-Di-O-isopropylidene-beta-D-fructopyranose can be achieved through various methods. One of the commonly used procedures involves the transformation of fructose to diacetonide using acetone. The diacetonide is then subjected to Grignard reagent to produce DFIP. The reaction can be carried out under mild conditions, which ensure high yield and purity of the product.

The characterization of DFIP can be done through various analytical methods, such as NMR, HPLC, and MS spectroscopy. These techniques can provide precise information about the chemical structure and purity of the compound.

Analytical Methods

1,2:4,5-Di-O-isopropylidene-beta-D-fructopyranose can be analyzed using various analytical techniques. The most commonly used methods include nuclear magnetic resonance (NMR) spectroscopy, high-performance liquid chromatography (HPLC), and mass spectrometry (MS).

NMR spectroscopy is a powerful technique that can provide detailed information about the structural and chemical properties of DFIP. In NMR analysis, the protons in the molecule are excited by a magnetic field, and their resulting emissions are recorded and analyzed. The technique can provide information about the chemical shifts, coupling constants, and rotational correlations of the DFIP molecule.

HPLC is a technique used to separate individual components of a mixture based on their interactions with a stationary phase and a mobile phase. HPLC can be used to quantitatively analyze the purity and quantity of DFIP in a sample.

MS is a technique used to measure the mass of a molecule or ion. This technique can provide information about the molecular weight, structure, and composition of DFIP. MS analysis can be carried out using various ionization techniques, such as electrospray ionization (ESI) and matrix-assisted laser desorption/ionization (MALDI).

Biological Properties

1,2:4,5-Di-O-isopropylidene-beta-D-fructopyranose is not actively used in biological systems, and its biological properties are limited. However, some studies have shown that DFIP can inhibit the activity of aldose reductase, an enzyme that is implicated in complications related to diabetes. This suggests that DFIP has potential as an anti-diabetic agent.

Toxicity and Safety in Scientific Experiments

1,2:4,5-Di-O-isopropylidene-beta-D-fructopyranose is considered to be non-toxic and safe for use in scientific experiments. However, appropriate safety precautions, such as the use of protective clothing and gloves, should be observed when handling the compound. As with any chemical compound, the potential risks associated with DFIP should be carefully assessed prior to its use in scientific experiments.

Applications in Scientific Experiments

1,2:4,5-Di-O-isopropylidene-beta-D-fructopyranose has a wide range of applications in scientific experiments. It is commonly used as a carbohydrate precursor or intermediate in the production of glycosyl donors. Glycosyl donors are used as activators in glycosylation reactions to produce glycosides, which are important biomolecules in living systems.

Current State of Research

The current research on 1,2:4,5-Di-O-isopropylidene-beta-D-fructopyranose is focused on its applications in organic synthesis and glycobiology. Several studies have been conducted to investigate the use of DFIP as a precursor or intermediate in the synthesis of biologically active compounds, such as oligosaccharides, glycosides, and glycoproteins.

Potential Implications in Various Fields of Research and Industry

1,2:4,5-Di-O-isopropylidene-beta-D-fructopyranose has potential implications in various fields of research and industry. Its use in the production of glycosyl donors and glycosides has important implications in glycobiology and biotechnology. Glycosylation is a critical process in the biosynthesis of important biomolecules such as hormones, antibodies, and enzymes.

Furthermore, the application of 1,2:4,5-Di-O-isopropylidene-beta-D-fructopyranose in the production of biologically active compounds such as oligosaccharides and glycoproteins has important implications in drug discovery and development. These compounds have potential therapeutic applications in the treatment of various diseases, including cancer, infectious diseases, and neurological disorders.

Limitations and Future Directions

Despite its many potential applications, 1,2:4,5-Di-O-isopropylidene-beta-D-fructopyranose has some limitations. One of the main limitations is the relatively limited availability of the compound and its derivatives. This limitation has limited its application in larger scale industrial processes.

Future directions of research in the field of DFIP will focus on ways to improve the yield and efficiency of its synthesis. Additionally, further research will likely focus on exploring the potential applications of DFIP in various fields, including biotechnology, drug discovery and development, and material science. The development of new methods for the synthesis and characterization of DFIP will further expand its applications and potential implications.