6-脱氧-D-葡萄糖 

6-Deoxy-D-glucose

6-Deoxyglucose (6-DG) is a glucose analogue that is widely used in scientific experiments to study glucose metabolism. It has physical and chemical properties similar to glucose, but its chemical structure is slightly different, which allows it to be selectively taken up by cells that are actively metabolizing glucose. This paper provides an overview of 6-DG, including its 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.

Introduction:

6-Deoxyglucose is a glucose analogue that is widely used in scientific experiments to study glucose metabolism. It is similar to glucose in physical and chemical properties, but its chemical structure is slightly different, which allows it to be selectively taken up by cells that are actively metabolizing glucose. This paper provides an overview of 6-DG, including its 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.

Definition and Background:

6-Deoxyglucose is a glucose analogue that lacks the hydroxyl group at the position 6 of the glucose molecule. It was first synthesized in the 1960s and has since been used as a tool to study glucose metabolism. 6-DG is taken up by cells through the glucose transporter (GLUT) system, but it cannot be metabolized by the cell due to the missing hydroxyl group, leading to its accumulation in the cell. This accumulation of 6-DG is proportional to the rate of glucose metabolism, making it a useful tool in glucose uptake and metabolism studies.

Physical and Chemical Properties:

6-Deoxyglucose is a white crystalline solid that is soluble in water and ethanol. It has a molecular weight of 164.16 and a chemical formula of C6H12O5. Its melting point is 105-107°C. The absence of the hydroxyl group at position 6 of the glucose molecule makes it resistant to phosphorylation by hexokinase, which is the first enzyme in the glycolytic pathway. This resistance allows 6-DG to accumulate in cells that are actively metabolizing glucose.

Synthesis and Characterization:

6-Deoxyglucose is synthesized from glucose through the removal of the hydroxyl group at position 6 of the glucose molecule. The synthesis of 6-DG can be achieved by several methods, including acid catalyzed dehydration, hydrogenation, and reduction. The purity and identity of 6-DG can be confirmed by various analytical methods, including nuclear magnetic resonance (NMR) spectroscopy, high-performance liquid chromatography (HPLC), and mass spectrometry (MS).

Analytical Methods:

Various analytical methods are used to measure the uptake and metabolism of 6-DG by cells. These methods include, but are not limited to, radioactive labeling, fluorescent labeling, HPLC, and MS. These methods allow researchers to determine the rate of glucose uptake and metabolism in different cell types and under different conditions.

Biological Properties:

6-Deoxyglucose has biological properties that make it a useful tool in studying glucose metabolism. It is taken up by cells through the GLUT system, but it cannot be metabolized due to the missing hydroxyl group, leading to its accumulation in the cell. This accumulation of 6-DG is proportional to the rate of glucose metabolism, making it a useful tool in glucose uptake and metabolism studies.

Toxicity and Safety in Scientific Experiments:

6-Deoxyglucose is generally considered safe in scientific experiments. However, like any chemical, it should be handled with care, and proper safety precautions should be taken. The LD50 for 6-DG in mice is greater than 2000 mg/kg, indicating a low toxicity. Its safety and toxicity in humans have not been extensively studied.

Applications in Scientific Experiments:

6-Deoxyglucose is widely used in scientific experiments to study glucose metabolism. It is a useful tool in glucose uptake and metabolism studies in various cell types under different conditions. It has also been used in functional imaging studies to study brain metabolism and to identify regions of the brain that are affected in different neurological disorders.

Current State of Research:

Research on 6-deoxyglucose continues to advance, and new applications are being discovered. Its usefulness in studying glucose metabolism has expanded beyond the fields of cell biology and neuroscience and into fields such as cancer biology and immunology.

Potential Implications in Various Fields of Research and Industry:

The potential implications of 6-deoxyglucose in various fields of research and industry are significant. In cancer biology, it has been shown to selectively target cancer cells, making it a potential tool in cancer diagnosis and treatment. In immunology, it has been shown to stimulate the immune system, making it potentially useful in the treatment of autoimmune diseases. Its potential applications in other fields, such as agriculture and biotechnology, are also being explored.

Limitations and Future Directions:

The use of 6-deoxyglucose in scientific experiments is not without limitations. One limitation is the variation in the GLUT system among different cell types, which can affect the uptake and accumulation of 6-DG. Another limitation is its lack of specificity, as it can be taken up by cells that are not actively metabolizing glucose. Future research should focus on developing more specific analogues of glucose that can be selectively taken up by cells that are actively metabolizing glucose.

Future Directions:

1. Development of more specific analogues of glucose that can be selectively taken up by cells that are actively metabolizing glucose.

2. Investigation of the potential therapeutic applications of 6-deoxyglucose in various fields, including cancer biology and immunology.

3. Study of the effects of 6-deoxyglucose on the microbiome and gut health.

4. Development of new analytical methods for studying glucose metabolism.

5. Investigation of the potential applications of 6-deoxyglucose in agriculture and biotechnology.

6. Study of the effects of 6-deoxyglucose on neuronal glucose metabolism and neurodegenerative diseases.

Title: Quinovose

CAS Registry Number: 7658-08-4

CAS Name: 6-Deoxy-D-glucose

Additional Names: D-glucomethylose; D-isorhamnose; D-epirhamnose; isorhodeose; epifucose; chinovose

Molecular Formula: C6H12O5

Molecular Weight: 164.16

Percent Composition: C 43.90%, H 7.37%, O 48.73%

Literature References: Isoln from cinchona bark: Freudenerg, Ber. 62, 373 (1929). Identity with D-glucomethylose: Votocek, Rác, Collect. Czech. Chem. Commun. 1, 239 (1929). Structure: Karrer, Boettcher, Helv. Chim. Acta 36, 570 (1953). Synthesis from 6-O-p-tolylsulfonyl-D-glucose: Schmidt, "6-Deoxy-a-D-glucose" in Methods in Carbohydrate Chemistry vol. I, R. L. Whistler, M. L. Wolfrom, Eds. (Academic Press, New York, 1962) pp 198-201. Alternate facile synthesis: V. K. Srivastava, L. M. Lerner, Carbohydr. Res. 64, 263 (1978).

Properties: Crystals from ethyl acetate, mp 146°. [a]D20 +73° (5 min) ® +30° (3 hr, final) (c = 8.3 in water). Sol in water, ethanol. Practically insol in ether, acetone.

Melting point: mp 146°

Optical Rotation: [a]D20 +73° (5 min) ® +30° (3 hr, final) (c = 8.3 in water)

Name: 6-Deoxy-D-Glucose; Chinovose; Quinovose; Isorhodeose; Glucomethylose; Isorhamnose; Epirhamnose

CAS: 7658-08-4       M.F.: C₆H₁₂O₅         M.W.: 164.16

References:

1. Tariq MA, Hayashi K, Biochem. Biophys. Res. Commun. 1995, 214, p568-75