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20847-05-6, 6-Azido-6-deoxy-D-glucose, CAS:20847-05-6

20847-05-6, 6-Azido-6-deoxy-D-glucose,
CAS:20847-05-6
C6H11N3O5 / 205.17
MFCD03265537

6-Azido-6-deoxy-D-glucose

 6-叠氮-6-脱氧-D-葡萄糖,

6-Azido-6-deoxy-D-glucose is a fluorescent compound that can be used as a probe for the visualization of glycosidase activity. The compound is synthesized from D-glucose by reacting it with 6-azidohexyl nitrate and sodium hydroxide in a chemoenzymatic reaction. This compound has been shown to bind to the cell nucleus, which can be observed using microscopy. The uptake of this compound into cells is dependent on the degree of polymerization, with monomers being taken up at a higher rate than oligomers or polymers. 6-Azido-6-deoxy-D-glucose is also an inhibitor of beta-cyclodextrin glycosidase, which prevents the hydrolysis of beta cyclodextrins.

6-Azido-6-deoxy-D-glucose is a synthetic compound that is derived from glucose. This molecule has been used widely in scientific experiments due to its unique physical and chemical properties. In recent years, 6-Azido-6-deoxy-D-glucose has gained significant attention as a potential tool for the development of new drugs and treatments. In this paper, we will explore the various characteristics of this molecule, including its properties, synthesis, biological properties, and potential applications.

Definition and Background

6-Azido-6-deoxy-D-glucose is a synthetic sugar molecule that is derived from glucose. It is a derivative of D-glucose, in which the hydroxyl (-OH) group at carbon-6 has been replaced with an azide (-N3) group. This substitution gives 6-Azido-6-deoxy-D-glucose unique properties, which make it a useful tool in scientific research.

Synthesis and Characterization

There are several methods for synthesizing 6-Azido-6-deoxy-D-glucose. One commonly used method involves the reaction of D-glucose with sodium azide in the presence of a catalyst, such as copper sulfate. This reaction yields 6-Azido-6-deoxy-D-glucose with a high degree of purity.

The characterization of 6-Azido-6-deoxy-D-glucose is typically done using analytical techniques such as nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry (MS). These techniques can provide detailed information about the molecular structure and purity of the compound.

Analytical Methods

Several analytical methods are used to detect and quantify 6-Azido-6-deoxy-D-glucose in samples. One commonly used method is high-performance liquid chromatography (HPLC), which separates the compound from other components in a sample based on its physicochemical properties. Other methods include gas chromatography (GC), capillary electrophoresis (CE), and thin-layer chromatography (TLC).

Biological Properties

6-Azido-6-deoxy-D-glucose has been found to interact with various proteins and enzymes in cells, which makes it a useful tool for exploring biological pathways. For example, it has been used as a tool to study the role of glucose transporters in cells. It has also been shown to inhibit the activity of glycosyltransferases, which are enzymes that play a role in the development of cancer.

Toxicity and Safety in Scientific Experiments

The toxicity of 6-Azido-6-deoxy-D-glucose is generally low. However, it can be toxic at high concentrations or when administered over prolonged periods. In scientific experiments, it is important to use the compound at concentrations that are safe for cells and animals. Researchers should also use protective equipment, such as gloves and goggles, to avoid direct contact with the compound.

Applications in Scientific Experiments

6-Azido-6-deoxy-D-glucose has several applications in scientific experiments, including:

1. Cell imaging: 6-Azido-6-deoxy-D-glucose can be used as a probe to visualize glucose uptake in cells.

2. Chemical biology: The compound can be used to study the biological functions of glucose and glucose transporters.

3. Cancer research: 6-Azido-6-deoxy-D-glucose can be used to inhibit the activity of glycosyltransferases, which are enzymes that play a role in the development of cancer.

Current State of Research

In recent years, there has been significant research on 6-Azido-6-deoxy-D-glucose. Researchers have explored its properties, synthesized new derivatives, and used it in various scientific experiments. However, there is still much to learn about this compound and its potential applications.

Potential Implications in Various Fields of Research and Industry

6-Azido-6-deoxy-D-glucose has significant potential in various fields of research and industry. Some potential applications include:

1. Drug development: The compound can be used as a tool for developing new drugs or treatments for diseases such as cancer, diabetes, and Alzheimer's disease.

2. Diagnostic imaging: 6-Azido-6-deoxy-D-glucose can be used in diagnostic imaging techniques such as positron emission tomography (PET) to visualize cellular glucose metabolism.

3. Biotechnology: The compound can be used to develop new biotechnological processes or products.

Limitations and Future Directions

Despite its potential applications, 6-Azido-6-deoxy-D-glucose has several limitations. For example, its synthesis can be challenging, and its reactivity can be difficult to control. Additionally, its toxicity at high concentrations limits its use in some scientific experiments.

Future directions for research on 6-Azido-6-deoxy-D-glucose include:

1. Development of new derivatives: Researchers can synthesize new derivatives of 6-Azido-6-deoxy-D-glucose with different properties and applications.

2. Exploration of biological pathways: The compound can be used to study the functions of glucose and glucose transporters in various biological pathways.

3. Drug development: Researchers can use 6-Azido-6-deoxy-D-glucose to develop new drugs or treatments for diseases such as cancer, diabetes, and Alzheimer's disease.

4. Biotechnology: The compound can be used to develop new biotechnological processes or products.

Conclusion

In conclusion, 6-Azido-6-deoxy-D-glucose is a synthetic compound with unique physical and chemical properties. It has several potential applications in scientific research and industry, including drug development, diagnostic imaging, and biotechnology. Although there are challenges associated with its synthesis and application, research on this compound is ongoing, and it holds significant promise for future developments in various scientific fields.

CAS Number20847-05-6
Product Name6-Azido-6-deoxy-D-glucose
IUPAC Name(2R,3S,4R,5R)-6-azido-2,3,4,5-tetrahydroxyhexanal
Molecular FormulaC6H11N3O5
Molecular Weight205.17 g/mol
InChIInChI=1S/C6H11N3O5/c7-9-8-1-3(11)5(13)6(14)4(12)2-10/h2-6,11-14H,1H2/t3-,4+,5-,6-/m1/s1
InChI KeyHEYJIJWKSGKYTQ-JGWLITMVSA-N
SMILESC(C(C(C(C(C=O)O)O)O)O)N=[N+]=[N-]
Canonical SMILESC(C(C(C(C(C=O)O)O)O)O)N=[N+]=[N-]
Isomeric SMILESC([C@H]([C@H]([C@@H]([C@H](C=O)O)O)O)O)N=[N+]=[N-]
CAS No: 20847-05-6 MDL No: MFCD03265537 Chemical Formula: C6H11N3O5 Molecular Weight: 205.17

References: 1. Biskup MB, Mueller JU, Weingart R, et al., Chem. Biochem. 2005, Vol6, Issue 6, p1007-1015

COA:

Product name:6-Azido-6-deoxy-D-glucose 

CAS:20847-05-6           Batch No: 20111207             Quantity:5.8g

Items

Standards

Results

Appearance

Yellowish or white power

Positive

Solubility

Soluble in H2O and

insoluble in ether

Complies

Appearance of solution

Dissolve0.5gin 10mL of H2O

and the solution should be clear

Complies

NMR and MS

Should comply

Complies

TLC (15%H2SO4-C2H5OH)

Should be one spot

one spot

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