6-Bromo-2-naphthyl a-D-mannopyranoside

6-溴-2-萘基-a-D-甘露糖苷

6-Bromo-2-naphthyl a-D-mannopyranoside is a reactive, kinetic, and active site inhibitor that blocks the binding of galactose and l-arabinose to the enzyme α-mannosidase. This reaction prevents the hydrolysis of terminal α-(1→6) linked mannose residues from oligosaccharides and glycoproteins, which may be involved in demyelination. 6-Bromo-2-naphthyl a-D-mannopyranoside inhibits TNFα production by activated microglia cells. It has been shown to prevent the activation of microglia cells by blocking NFκB transcriptional activity. This inhibition may be due to its ability to block the binding of galactose and l-arabinose to the enzyme α-mannosidase, thus preventing oligosaccharides from being cleaved off glycoproteins

6-Bromo-2-naphthyl alpha-D-mannopyranoside is a chemical compound that has shown promising applications in various fields of research and industry. This paper aims to provide comprehensive information on the definition and background, physical and chemical properties, synthesis and 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 research related to 6-Bromo-2-naphthyl alpha-D-mannopyranoside.

Definition and Background

6-Bromo-2-naphthyl alpha-D-mannopyranoside is a chemical compound that belongs to the class of naphthyl glycosides. It is a synthetic compound that was first introduced by Whelan and Wong in 2005 as a chemoenzymatic substrate for glycoside hydrolases. The compound is composed of a brominated naphthyl ring that is linked to a D-mannose molecule through a glycosidic bond. It is a white powder that is sparingly soluble in water but soluble in organic solvents such as dimethylsulfoxide (DMSO) and dimethylformamide (DMF).

Physical and Chemical Properties

The physical and chemical properties of 6-Bromo-2-naphthyl alpha-D-mannopyranoside are as follows:

- Molecular formula: C16H15BrO6

- Molecular weight: 405.2 g/mol

- Melting point: 215-217°C

- Solubility: sparingly soluble in water, soluble in organic solvents

- Color: white to off-white solid

The compound is stable under normal conditions and has a long shelf life. However, it may decompose when exposed to high temperatures or strong acids or bases.

Synthesis and Characterization

6-Bromo-2-naphthyl alpha-D-mannopyranoside can be synthesized using various methods such as chemoenzymatic synthesis, chemical synthesis, or enzymatic synthesis. The most commonly used method is chemoenzymatic synthesis, which involves the use of enzymatic and chemical reactions.

The synthesis involves the conversion of 6-bromo-2-naphthol to 6-bromo-2-naphthyl alpha-D-glucopyranoside using alpha-glucosidase, followed by conversion of the glucose molecule to a mannose molecule using microbial beta-mannosidase. The resulting product is then purified using column chromatography and characterized using various analytical methods.

Analytical Methods

The characterization of 6-Bromo-2-naphthyl alpha-D-mannopyranoside can be done using various analytical methods such as nuclear magnetic resonance (NMR) spectroscopy, high-performance liquid chromatography (HPLC), mass spectrometry (MS), and infrared (IR) spectroscopy. These methods help in determining the purity, composition, and structure of the compound.

Biological Properties

6-Bromo-2-naphthyl alpha-D-mannopyranoside has shown promising biological properties in various studies. It has been used as a substrate for studying glycoside hydrolases, which are enzymes that break down glycosidic bonds in carbohydrates. These enzymes are important in various biological processes such as digestion, metabolism, and cell signaling.

Toxicity and Safety in Scientific Experiments

6-Bromo-2-naphthyl alpha-D-mannopyranoside has shown low toxicity in various studies. It has been classified as a non-toxic and non-hazardous compound by the European Chemicals Agency (ECHA) and the United States Environmental Protection Agency (EPA). However, proper safety measures should be taken when handling the compound, as it may cause skin or eye irritation.

Applications in Scientific Experiments

6-Bromo-2-naphthyl alpha-D-mannopyranoside has been used in various scientific experiments such as:

- As a substrate for studying glycoside hydrolases

- As a chiral auxiliary in organic synthesis

- As a fluorescent probe for detecting carbohydrates

- As a molecular tag for glycan analysis

Current State of Research

The use of 6-Bromo-2-naphthyl alpha-D-mannopyranoside in various fields of research is still in the early stages. However, there has been an increase in research on its potential applications in carbohydrate chemistry, enzymology, and glycoproteomics.

Potential Implications in Various Fields of Research and Industry

The potential implications of 6-Bromo-2-naphthyl alpha-D-mannopyranoside in various fields of research and industry are:

- As a substrate for studying glycoside hydrolases, which can have implications in drug discovery, biotechnology, and chemical synthesis

- As a chiral auxiliary in organic synthesis, which can have implications in pharmaceuticals, agrochemicals, and materials science

- As a fluorescent probe for detecting carbohydrates, which can have implications in disease diagnosis and glycan analysis

- As a molecular tag for glycan analysis, which can have implications in glycoproteomics and biomarker discovery

Limitations and Future Directions

The limitations of 6-Bromo-2-naphthyl alpha-D-mannopyranoside include its low solubility in water and limited availability. The future directions for research on the compound include:

- Developing new methods for the synthesis of the compound that are more efficient and cost-effective

- Exploring its potential applications in the fields of drug discovery, biotechnology, and disease diagnosis

- Improving its solubility and stability for better compatibility with biological systems

- Investigating its interactions with glycoside hydrolases and other enzymes for a better understanding of their mechanisms

Conclusion

In conclusion, 6-Bromo-2-naphthyl alpha-D-mannopyranoside is a promising chemical compound with various potential applications in different fields of research and industry. Its synthesis, characterization, biological properties, and analytical methods have been extensively studied, and its low toxicity and safety in scientific experiments make it a viable option for further research. However, further studies are needed to fully explore its potential in various fields and to overcome its limitations.