D-Glucal

D-葡萄糖烯,

D-Glucal is a protonated d-glucal, which is a simple sugar. It reacts with the electron acceptor oxygen to form an oxidized product. This product can be reduced back to the original molecule by using a reducing agent, such as sodium borohydride or sodium dithionite. D-Glucal has been shown to inhibit the growth of tumor cells in mice that are resistant to other anticancer drugs. D-Glucal inhibits transcription and replication of DNA by binding to the DNA-dependent RNA polymerase and blocking its ability to transcribe messenger RNA (mRNA). The enzyme is also inhibited by glycosidic bond architectures that prevent it from binding to the DNA template strand. D-Glucal also has an effect on protein synthesis because it binds to proteins and prevents them from performing their normal functions. D-Glucal has been used as a model system for studying cellular processes in mammalian cells

d-Glucal is a cyclic aldose that belongs to the glucose family. It exists as a white solid, soluble in water, with a sweet taste. Its molecular structure consists of a six-membered pyranose ring, containing five carbon atoms and one oxygen atom. d-Glucal is a crucial intermediate in carbohydrate chemistry and an important building block in the synthesis of oligosaccharides and glycoconjugates. The goal of this paper is to provide a comprehensive overview of d-Glucal with a focus on its definition, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity, 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.

Definition and Background:

d-Glucal is a carbohydrate, specifically an aldohexose. It is a cyclic isomer of glucose composed of five carbon atoms and one oxygen atom in the form of a pyranose ring. d-Glucal is typically used as a protective group for the production of oligosaccharides, glycosides, and glycoconjugates. d-Glucal bears a primary hydroxyl group that undergoes regioselective reactions, unlike other aldohexoses. Due to this regioselectivity, d-Glucal is an essential intermediate in the synthesis of oligosaccharides.

Synthesis and Characterization:

d-Glucal can be synthesized through various methods, including the isomerization of glucose, ring-opening reactions, and the oxidation of d-glucitol. The synthesis of d-Glucal usually involves the introduction of a protective group on the glucose molecule, followed by a series of chemical reactions, including reduction or oxidation, to obtain the desired product. d-Glucal is characterized through various techniques, including NMR spectroscopy, X-ray crystallography, IR spectroscopy, and mass spectrometry.

Analytical Methods:

Various analytical methods are employed to identify and quantify d-Glucal, depending on the application. These methods include NMR spectroscopy, high-performance liquid chromatography (HPLC), gas chromatography (GC), thin-layer chromatography (TLC), and IR spectroscopy.

Biological Properties:

d-Glucal has various potential therapeutic applications. For instance, it has been shown to exhibit antibacterial activity against Staphylococcus aureus and Escherichia coli. Furthermore, d-Glucal has been shown to inhibit the growth of cancer cells in vitro, demonstrating its anti-tumor properties. Additionally, d-Glucal can be used as a substrate to produce various enzymes, including alpha-glucosidase, AmyR, and AmyC.

Toxicity and Safety in Scientific Experiments:

In scientific experiments, d-Glucal has been shown to have low toxicity. However, systemic and subcutaneous administration of d-Glucal can lead to liver and kidney damage. Researchers must adhere to safety guidelines when handling d-Glucal to limit exposure and minimize any adverse effects.

Applications in Scientific Experiments:

d-Glucal has a wide range of applications in scientific experiments. It can be used as a starting material in the synthesis of oligosaccharides, glycosides, and glycoconjugates. d-Glucal can also serve as a scaffold for the preparation of synthetic carbohydrate vaccines. Additionally, d-Glucal is an important building block in the synthesis of glycolipids.

Current State of Research:

d-Glucal has been studied extensively in the areas of carbohydrate chemistry, biochemistry, and pharmaceuticals. Current research focuses on the synthesis of novel oligosaccharides and glycopeptides using d-Glucal as a starting material. Additionally, researchers are exploring the anti-tumor properties of d-Glucal and its potential therapeutic applications.

Potential Implications in Various Fields of Research and Industry:

d-Glucal has vast potential implications in various fields, including the development of new drugs, vaccines, and biosensors. d-Glucal can be used to create conjugate vaccines that mimic the carbohydrate antigens found on the surface of bacteria or viruses. This approach can combat diseases such as cancer, HIV, and bacterial infections. d-Glucal can also be used to develop biosensors that detect sugar molecules rapidly.

Limitations:

One of the limitations of d-Glucal is that its synthesis is challenging and requires various steps. Additionally, d-Glucal is not naturally occurring, which limits its use in organic synthesis.

Future Directions:

To further expand the applications of d-Glucal, researchers can consider the following future directions:

1. Develop new synthetic routes for the production of d-Glucal to simplify the synthesis process.

2. Explore the potential of d-Glucal as a biosensor platform for sugar detection.

3. Investigate the use of d-Glucal-derived glycoconjugates as therapeutic agents.

4. Assess the potential of d-Glucal in facilitating the synthesis of complex carbohydrates.

5. Develop more stable and efficient d-Glucal derivatives that could be used in organic synthesis.

Conclusion:

In conclusion, d-Glucal is a versatile carbohydrate with various applications in scientific research and industry. Its unique properties, including its regioselectivity, make it a valuable building block in carbohydrate chemistry. The future of d-Glucal research looks promising, and this molecule could play a significant role in the development of new therapeutic agents, vaccines, and biosensors.

Product name: D-Glucal                                                                CAS: 13265-84-4

M.F.: C₆H₁₀O₄        M.W.: 146.14      Batch No: 20130406           Quantity:1700g

References:

1. Korytnyk W, Dodson-Simmons O, Carbohydr. Res. 1984, Aug 1, p157