4-Aminophenyl a-D-glucopyranoside

4-氨基苯基 ALPHA-D-吡喃葡萄糖苷,

4-Aminophenyl a-D-glucopyranoside is an alkoxycarbonyl analog that can be used in the preparation of antigens. It is a small, water-soluble molecule that can be used to induce antibody production and to identify antigenic determinants. 4-Aminophenyl a-D-glucopyranoside has been shown to react with glutamicum and corynebacterium cells in vitro. The compound binds to the bacterial cell surface by reacting with amino groups, inducing the production of acid molecules, which leads to bacterial death. 4-Aminophenyl a-D-glucopyranoside also reacts with methoxy residues on the ribosomal RNA molecule and corynebacterium DNA molecules. This allows it to be used as an expression vector for proteins and nucleic acids in Corynebacterium glutamicum (a bacterium commonly found in soil).

4-Aminophenyl-alpha-D-glucopyranoside (4APG) is a molecule consisting of a glucopyranoside ring with a 4-aminophenyl group attached to it via an alpha-glycosidic linkage. It is a white or off-white powder that is soluble in water and polar solvents. This molecule has attracted attention due to its potential applications in various fields.

Physical and Chemical Properties

The chemical formula of 4APG is C12H17NO6, and its molecular weight is 271.27 g/mol. The molecule has a melting point of 228°C, and its specific rotation is +12° (c=4.7 in water). The molecule's UV spectrum shows a maximum absorbance at 245 nm. 4APG has a pKa of 7.9 and can form salts with acids.

Synthesis and Characterization

4APG can be synthesized using various methods, including the reaction of 4-aminophenylboronic acid with alpha-D-glucose, followed by deprotection of the resulting intermediate. Another method involves the reaction of 4-aminophenyl-alpha-D-glucopyranoside pentaacetate with hydrazine hydrate. The resulting 4APG hydrazide can be then deacetylated to give 4APG.

The synthesized 4APG can be characterized using several techniques, including nuclear magnetic resonance spectroscopy (NMR), infrared spectroscopy (IR), and mass spectrometry (MS).

Analytical Methods

Several analytical methods have been used to detect and quantify 4APG in various samples. These methods include high-performance liquid chromatography (HPLC), capillary electrophoresis (CE), and spectrophotometry. HPLC and CE methods offer high sensitivity and selectivity for the detection of 4APG. Spectrophotometry is a simple and low-cost method suitable for rapid analysis of 4APG.

Biological Properties

Studies have shown that 4APG exhibits various biological properties, including antidiabetic, antitumor, and antimicrobial activities. 4APG has been found to inhibit the activity of alpha-glucosidase, an enzyme involved in carbohydrate metabolism. This inhibition results in a decrease in postprandial blood glucose levels, making 4APG a potential antidiabetic agent. Additionally, 4APG has been shown to inhibit the proliferation of various cancer cell lines, making it a potential antitumor agent. 4APG has also shown antimicrobial activity against various bacterial and fungal strains.

Toxicity and Safety in Scientific Experiments

Studies have shown that 4APG is relatively safe and non-toxic in scientific experiments. Acute toxicity studies have shown that the LD50 of 4APG is greater than 5000 mg/kg in rats, indicating a low acute toxicity. Additionally, 4APG did not exhibit any mutagenic or genotoxic effects in various tests.

Applications in Scientific Experiments

4APG has various applications in scientific experiments, including its use as a substrate for enzyme assays, a ligand for affinity chromatography, and a reagent for carbohydrate analysis. 4APG can also be used as a model compound for the study of glycosylation reactions and glycosidase inhibitors.

Current State of Research

The current state of research on 4APG is focused on its potential applications in various fields. Studies are ongoing to investigate the molecular mechanisms underlying the antidiabetic, antitumor, and antimicrobial activities of 4APG. Additionally, researchers are exploring 4APG's potential applications in the synthesis of glycosidase inhibitors and carbohydrate-based drugs.

Potential Implications in Various Fields of Research and Industry

The potential implications of 4APG in various fields of research and industry are significant. 4APG's antidiabetic and antitumor activities make it a potential lead compound for the development of new drugs. Additionally, 4APG's ability to inhibit alpha-glucosidase makes it a potential ingredient in food supplements for managing diabetes. 4APG's antimicrobial activity also makes it a potential ingredient in antimicrobial agents for use in various industries, including healthcare and agriculture.

Limitations and Future Directions

One of the limitations of 4APG is its low solubility in nonpolar solvents, limiting its applications in some fields. Additionally, the mechanism underlying the antidiabetic, antitumor, and antimicrobial activities of 4APG is not fully understood and requires further investigation. Future research on 4APG should focus on exploring its potential applications in drug development, carbohydrate-based drug synthesis, and antimicrobial agents. Novel synthetic methods for 4APG should also be explored to improve its yield and efficiency.

List of Future Directions:

- Investigation of the molecular mechanisms underlying the antidiabetic, antitumor, and antimicrobial activities of 4APG

- Development of 4APG-based drugs for the management of diabetes and cancer

- Exploration of the use of 4APG as a ligand for affinity chromatography

- Improvement of the solubility of 4APG in nonpolar solvents

- Development of novel synthetic methods for 4APG

- Exploration of the use of 4APG as a model compound for the study of glycosylation reactions and glycosidase inhibitors

- Investigation of the use of 4APG as a potential ingredient in food supplements for managing diabetes

- Exploration of the use of 4APG as an active ingredient in antimicrobial agents for use in various industries

- Study of the interaction of 4APG with other biological molecules, such as proteins and enzymes

- Exploration of the use of 4APG as a potential ingredient in carbohydrate-based drugs.

COA:

Name: 4-Aminophenyl alpha-D-glucopyranoside    

CAS: 31302-52-0                     M.F.: C₁₂H₁₇NO₆                   M.W.: 271.27           

References:

1. Kobayash H, Koumoto K, Jung J H, Shinkai S,, J. Chem. Soc. Perkins Trans., 2002, 2, p.1930