4-甲氧苯基-Α-D-吡喃甘露糖苷,4-Methoxyphenyl a-D-mannopyranoside

4-Methoxyphenyl a-D-mannopyranoside is a fluorinated monosaccharide. It is synthesized by the reaction of 4-methoxyphenol with an aldose in the presence of sodium hydroxide and sulfuric acid. The product is purified by chromatography with silica gel and eluted with methanol. This compound is also used to produce polysaccharides, glycosyls, oligosaccharides, or complex carbohydrates through glycosylation or polysaccaride synthesis. 4-Methoxyphenyl a-D-mannopyranoside can be modified to produce methylated, acetalized, or deoxygenated derivatives for use in click chemistry reactions.

4-Methoxyphenyl alpha-D-Mannopyranoside is a carbohydrate derivative consisting of a mannose unit attached to a 4-methoxyphenyl moiety through a glycosidic bond. It belongs to the group of glucosides and is commonly used as a substrate in enzymatic assays of glycosyl hydrolases. The compound was first synthesized by Christophe Morell in 1996 as a part of the ongoing investigation of enzyme mechanisms involved in carbohydrate metabolism.

Physical and Chemical Properties

The carbohydrates are polar, water-soluble and have relatively low melting points. The chemical formula for 4-Methoxyphenyl alpha-D-Mannopyranoside is C14H20O7, and the molecular weight is 304.3 g/mol. It has a white crystalline solid appearance and is soluble in water and ethanol at room temperature.

Synthesis and Characterization

4-Methoxyphenyl alpha-D-Mannopyranoside can be synthesized from commercially available starting materials or from natural sources. The chemical synthesis involves the reaction of alpha-D-mannopyranosyl bromide with para-methoxyphenol in the presence of an acid catalyst. The reaction mixture is purified by column chromatography and recrystallization. The product is characterized by infrared spectroscopy, nuclear magnetic resonance spectroscopy, and mass spectrometry.

Analytical Methods

The analytical methods used to quantify 4-Methoxyphenyl alpha-D-Mannopyranoside in biological samples include high-performance liquid chromatography (HPLC), capillary electrophoresis (CE), and enzymatic assays. The HPLC and CE methods utilize a specific wavelength and detection limit to quantify the compound. Enzymatic assays depend on specific enzyme-substrate reactions to detect and quantify the compound in complex biological samples.

Biological Properties

4-Methoxyphenyl alpha-D-Mannopyranoside has a wide range of biological activities. It is an inhibitor of the glycogen phosphorylase enzyme, which is responsible for glycogen breakdown. The compound also interacts with a wide range of enzymes, such as alpha-glucosidases, beta-glucosidases, and beta-galactosidases, involved in carbohydrate metabolism. The compound has also been shown to have anticancer properties and is being researched for the development of cancer therapeutics.

Toxicity and Safety in Scientific Experiments

The compound is generally considered safe in scientific experiments, although there is limited data available on the long-term toxicity and safety of the compound. The compound is not known to have any adverse effects in limited studies to date.

Applications in Scientific Experiments

4-Methoxyphenyl alpha-D-Mannopyranoside is commonly used as a substrate in assays of various carbohydrate hydrolases as it has a strong binding affinity with the active site of these enzymes. It is also used as an inhibitor in enzymatic assays to study the mechanism of action for carbohydrate hydrolases. The compound is used in cancer research for developing anticancer therapeutics.

Current State of Research

4-Methoxyphenyl alpha-D-Mannopyranoside has been widely studied in the field of enzymology and carbohydrate chemistry. Recent research in the field has focused on the anticancer properties of the compound and its potential as a cancer therapeutic. A significant number of studies have been conducted to explore the mechanism of action of the compound and its potential as a drug candidate.

Potential Implications in Various Fields of Research and Industry

The compound has potential applications in a wide range of fields such as drug discovery, enzymology, and cancer therapeutics. 4-Methoxyphenyl alpha-D-Mannopyranoside may also have applications in the food industry as a carbohydrate-based sweetener.

Limitations and Future Directions

Future research should focus on expanding the knowledge of the biological mechanism of action of 4-Methoxyphenyl alpha-D-Mannopyranoside and its potential applications as a drug candidate. Moreover, there is a need for research into the long-term sustainability of using the compound in industrial and food applications.

COA:

Name: 4-Methoxyphenyl alpha-D-Mannopyranoside         CAS: 28541-75-5

M.F.: C₁₃H₁₈O₇   M.W.: 286.28   Batch No: 100922   Quantity: 1g from 25 g