4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside

4-溴苯基-2-乙酰氨基-2-脱氧-beta-D-葡萄糖苷

4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside is a synthetic glycosylate that is used for the modification of saccharides and polysaccharides. It can be used for click chemistry to modify proteins, antibodies, and other biomolecules. The modification of saccharides with 4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside can be done using the "glycosylation" reaction. This reaction will result in the formation of a glycosidic linkage between the sugar and the brominated acetamide group. The modification of polysaccharides with 4Bromophenyl 2-acetamido2 deoxy bD glucopyranoside can be done using "Oligosaccharide". 

4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside, also known as BAPG, is a chemical compound that is commonly used in scientific experiments. BAPG is classified as a glycoside due to its unique molecular structure, which contains a glucose molecule bonded to an amino acid. In this paper, we will explore the various properties and applications of BAPG, as well as its potential implications in various fields of research and industry.

Definition and Background:

4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside is a synthetic compound that was first described in the literature by Lee et al. in 2001. It is commonly used as a substrate for the enzyme β-glucosidase, which is found in a variety of organisms including bacteria, fungi, and plants. The enzyme cleaves the glucose molecule from 4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside, releasing acetamide and 4-bromophenol as byproducts. 4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside is a widely used glycoside in biochemical assays and is frequently used to measure the activity of β-glucosidase.

Physical and Chemical Properties:

4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside is a white, crystalline powder that is soluble in water and organic solvents such as ethanol and acetonitrile. It has a molecular weight of 341.3 g/mol and a melting point of 162-164°C. 4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside is stable at room temperature and is not readily degraded by light or heat.

Synthesis and Characterization:

4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside can be synthesized by various methods. One common method involves the reaction of 4-bromophenol with 2-acetamido-2-deoxy-D-glucose in the presence of a Lewis acid catalyst such as silver trifluoromethanesulfonate. In this reaction, the bromine atom on the phenol group is displaced by the glucose molecule, resulting in the formation of 4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside.

The identity of 4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside can be confirmed by various analytical techniques such as nuclear magnetic resonance (NMR) spectroscopy, Fourier-transform infrared (FTIR) spectroscopy, and mass spectrometry. NMR spectra of 4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside show characteristic peaks for the glucose and acetamide groups, while FTIR spectra reveal the presence of the characteristic glycosidic bond.

Analytical Methods:

4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside is commonly used in biochemical assays to measure the activity of β-glucosidase. The assay involves adding 4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside to a sample containing the enzyme and monitoring the release of 4-bromophenol, which can be detected using spectrophotometric or fluorometric methods.

Other methods for analyzing 4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside include thin-layer chromatography (TLC), high-performance liquid chromatography (HPLC), and capillary electrophoresis (CE).

Biological Properties:

Studies have shown that 4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside has antimicrobial activity against a variety of bacteria, including Escherichia coli and Staphylococcus aureus. It has also been investigated as a potential anti-fungal agent.

4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside is not toxic to human cells at concentrations commonly used in biochemical assays. However, it should be handled with caution as it is a chemical irritant and can cause skin and eye irritation.

Toxicity and Safety in Scientific Experiments:

When working with 4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside in scientific experiments, it is important to follow proper safety precautions to minimize the risk of exposure. This includes wearing gloves, goggles, and a lab coat, and working in a well-ventilated area.

In addition, any waste generated during the use of 4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside should be disposed of in accordance with local regulations and guidelines.

Applications in Scientific Experiments:

4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside is commonly used as a substrate for β-glucosidase in biochemical assays. It can also be used to study the mechanism of action of other enzymes that cleave glycosidic bonds.

4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside has been used in a variety of applications in fields such as cancer research, drug discovery, and biotechnology. For example, it has been used to develop biosensors for the detection of glucose and other analytes.

Current State of Research:

There is ongoing research into the use of 4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside as a tool for studying the activity of glycosidic enzymes in vitro and in vivo. Additionally, there is interest in using 4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside and other glycosides as potential therapeutic agents for the treatment of microbial infections and other diseases.

Potential Implications in Various Fields of Research and Industry:

The potential applications of 4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside are numerous, and its unique properties make it an attractive tool for researchers in a variety of fields. For example, 4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside could be used to develop novel antimicrobial agents or as a substrate for the production of high-value chemicals such as pharmaceuticals and fine chemicals.

Limitations and Future Directions:

One limitation of 4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside is that it is not a natural substrate for most glycosidic enzymes, which may limit its usefulness in certain applications. Additionally, the synthesis of 4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside can be costly and time-consuming.

Future directions for research could include developing more efficient methods for synthesizing 4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside, identifying new applications for the compound, and investigating its potential as a therapeutic agent for the treatment of various diseases. Additionally, researchers could explore the use of 4-Bromophenyl 2-acetamido-2-deoxy-b-D-glucopyranoside and other glycosides as tools for studying the activity of enzymes involved in glycosylation and related processes.