3-O-Methyl-D-glucopyranose

3-O-甲基-D-葡萄糖

3-O-Methyl-alpha-D-glucopyranose, also known as 3-O-Methyl-D-glucose, is a monosaccharide with the molecular formula C7H14O6. It is a methylated glucose molecule in which the hydroxyl group on the 3rd carbon atom is replaced by a methyl group. This molecule is widely used as a tracer and substrate in biochemical and metabolic studies. It was first isolated and identified by Fischer and Armstrong in 1902.

Physical and Chemical Properties:

3-O-Methyl-alpha-D-glucopyranose is a white crystalline powder with a sweet taste. It is water-soluble and exhibits optical rotation. Its melting point is around 168-171 °C. The molecule has several functional groups, including hydroxyl and methyl, which make it chemically reactive and useful in biological studies.

Synthesis and Characterization:

In general, 3-O-Methyl-alpha-D-glucopyranose can be synthesized by the reaction of methyl iodide with alpha-D-glucopyranose in alkaline conditions. The product is purified by chromatography or recrystallization. The identity and purity of the molecule are confirmed by various analytical methods, including NMR spectroscopy, mass spectrometry, and HPLC.

Analytical Methods:

Several analytical methods are used to identify and quantify 3-O-Methyl-alpha-D-glucopyranose in biological and chemical samples. HPLC is the most common method for its detection because it is very sensitive and can detect very low concentrations of the molecule. Other methods, such as capillary electrophoresis and GC-MS, are also used for its analysis.

Biological Properties:

3-O-Methyl-alpha-D-glucopyranose is used as a substrate in various biochemical assays and metabolic studies. It is a non-metabolizable glucose analog that can be used to measure glucose transport, metabolism, and utilization in cells and tissues. It is also used as a tracer to measure glucose turnover rates and the fractional synthesis rate of glycogen.

Toxicity and Safety in Scientific Experiments:

According to the available literature, 3-O-Methyl-alpha-D-glucopyranose is considered safe and non-toxic in scientific experiments. However, caution is required when administering it to animals or human subjects, and proper ethical guidelines and regulations must be followed.

Applications in Scientific Experiments:

3-O-Methyl-alpha-D-glucopyranose has many applications in scientific experiments. Its ability to mimic glucose metabolism and transport makes it useful in studying various metabolic pathways, including glycolysis, gluconeogenesis, and glycogen synthesis. It is also used in research related to diabetes, obesity, cancer, and other diseases.

Current State of Research:

Current research on 3-O-Methyl-alpha-D-glucopyranose is focused on several areas, including its use as a tracer for glucose metabolism in cancer cells, its effect on insulin secretion and glucose uptake in pancreatic beta-cells, and its potential as a therapeutic agent in various diseases. Research is also ongoing on its transport mechanisms across the blood-brain barrier and its role in brain metabolism.

Potential Implications in Various Fields of Research and Industry:

3-O-Methyl-alpha-D-glucopyranose has potential implications in various fields of research and industry. Its utility as a glucose analog and tracer makes it useful in many biochemical assays and metabolic studies. It may also have clinical applications in diabetes management, cancer diagnosis, and other diseases. Furthermore, it may have industrial applications in the food and beverage industry as a sweetener or preservative.

Limitations and Future Directions:

Despite its usefulness, 3-O-Methyl-alpha-D-glucopyranose has some limitations in scientific research, including its potential interaction with other molecules and its inability to mimic all aspects of glucose metabolism. Future directions in research include developing new synthetic methods to produce the molecule, optimizing its use as a tracer, and exploring its therapeutic potential in various diseases. Additionally, further research is needed to understand its interaction with other biomolecules and its potential side effects in biological systems.

Some areas of research that could benefit from further exploration include:

1. Investigating the role of 3-O-Methyl-alpha-D-glucopyranose in brain metabolism and its potential as a neuroprotective agent.

2. Developing new methods to improve the specificity and sensitivity of 3-O-Methyl-alpha-D-glucopyranose as a tracer for glucose metabolism.

3. Exploring the potential use of 3-O-Methyl-alpha-D-glucopyranose in cancer diagnosis and treatment.

4. Investigating the effects of 3-O-Methyl-alpha-D-glucopyranose on insulin sensitivity and glucose uptake in human subjects.

5. Developing new derivatives of 3-O-Methyl-alpha-D-glucopyranose with altered functional properties and improved biocompatibility.

Product name: 3-O-Methyl-D-glucopyranose

CAS: 13224-94-7 or 3370-81-8      M.F.: C₇H₁₄O₆      M.W.: 194.18