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210418-04-5 ,4-Nitrophenyl 2-azido-2-deoxy-a-D-galactopyranoside, CAS:210418-04-5

210418-04-5 ,4-Nitrophenyl 2-azido-2-deoxy-a-D-galactopyranoside,
CAS:210418-04-5
C12H14N4O7 / 326.26
MFCD00270053

4-Nitrophenyl 2-azido-2-deoxy-a-D-galactopyranoside

4-硝基苯基-2-叠氮-2-脱氧-α-D-吡喃半乳糖苷,

4-Nitrophenyl 2-azido-2-deoxy-a-D-galactopyranoside is a superior chromogenic substrate for the precise determination of alpha-D-galactosidase enzyme activity. This substrate features a unique 2-azido moiety providing enhanced sensitivity and specificity in biochemical assays. Upon enzymatic cleavage, it releases the highly fluorescent compound 4-nitrophenol, which simplifies quantification and tracking of enzyme activity in applications such as drug discovery, genetic studies, and enzyme inhibition assays.

4-Nitrophenyl 2-azido-2-deoxy-a-D-galactopyranoside is a carbohydrate derivative commonly known as NPAG. It is an azide-containing galactoside that is used to study the behavior of specific enzymes and proteins that can recognize and cleave carbohydrates. NPAG has been used as a potent inhibitor for these enzymes and as a general tool in the field of glycobiology.

Synthesis and Characterization:

NPAG can be synthesized by a method called "click chemistry," where an alkyne-containing galactoside is reacted with an azide-containing compound in the presence of copper catalysts. The reaction leads to the formation of a triazole ring, which gives stability to the compound. The synthesis of NPAG is a straightforward and efficient process, and the compound can be characterized using standard techniques such as NMR spectroscopy, mass spectrometry, and elemental analysis.

Analytical Methods:

Several analytical methods have been developed to detect and quantify NPAG in biological samples. These methods include HPLC, LC-MS/MS, and capillary electrophoresis. HPLC is the most commonly used technique due to its high sensitivity and specificity. These methods have been used to study the kinetics of NPAG hydrolysis by enzymes and to evaluate the potency of NPAG as an inhibitor.

Biological Properties:

NPAG is a substrate analogue that can be recognized and cleaved by specific enzymes and proteins in the glycoside hydrolase family. These enzymes are involved in various biological processes, including the degradation of plant material, the recycling of cell wall components, and the production of glycoproteins and glycolipids. NPAG has been used to study the substrate specificity and kinetics of these enzymes and to identify their catalytic mechanisms.

Toxicity and Safety in Scientific Experiments:

NPAG is generally considered safe for laboratory use, but appropriate safety measures should be taken when handling the compound. NPAG can be toxic if ingested or inhaled, and it can cause skin and eye irritation. Therefore, it is recommended to wear personal protective equipment such as gloves and goggles when working with NPAG.

Applications in Scientific Experiments:

NPAG has several applications in scientific experiments, including:

- Investigating the substrate specificity and kinetics of glycoside hydrolase enzymes

- Identifying the catalytic mechanisms of these enzymes

- Studying the glycosylation patterns of glycoproteins and glycolipids

- Developing new inhibitors for glycoside hydrolases

- Designing biosensors for carbohydrate recognition

Current State of Research:

There is ongoing research on the synthesis and characterization of NPAG derivatives with improved properties such as stability and water solubility. Additionally, NPAG is being used to study the structure and function of various glycoside hydrolases, which may lead to the development of new drugs and biocatalysts.

Potential Implications in Various Fields of Research and Industry:

NPAG has the potential to be used in several fields of research and industry, including:

- Biocatalysis: NPAG can be used as a substrate for the production of high-value products such as biofuels and pharmaceuticals.

- Drug discovery: NPAG can be used to develop new drugs that target glycoside hydrolases involved in diseases such as cancer, diabetes, and infections.

- Material science: NPAG can be used to develop new materials with specific carbohydrate recognition properties.

- Food and agriculture: NPAG can be used to study the structure and function of enzymes involved in the degradation of plant material, which may lead to the development of new processes for the production of biofuels and bio-based products.

Limitations and Future Directions:

While NPAG has several advantages as a tool in glycobiology, there are several limitations to its use. These limitations include its sensitivity to light, its low solubility in water, and its labile nature. However, ongoing research is focused on developing new NPAG derivatives with improved properties, such as higher water solubility, better stability, and increased potency as inhibitors. Furthermore, the development of new analytical techniques and biosensors will enable the detection and quantification of NPAG in complex biological matrices, leading to a deeper understanding of its biological role.

Future directions for the research on NPAG include but are not limited to:

- Developing new NPAG derivatives with improved properties and potency as inhibitors

- Conducting more in-depth structural studies of glycoside hydrolases in complex with NPAG

- Developing new biosensors for the detection and quantification of NPAG in biological samples

- Applying NPAG in new fields of research and industry such as biocatalysis and material science

- Investigating the potential of NPAG as a drug target for diseases such as cancer and diabetes.

In conclusion, NPAG is a versatile and useful compound in the field of glycobiology. It has several applications in scientific experiments, and its potential implications in various fields of research and industry are significant. The ongoing research on NPAG derivatives and its biological role will lead to new insights and opportunities for the development of new drugs and biocatalysts.

CAS Number210418-04-5
Product Name4-Nitrophenyl 2-azido-2-deoxy-a-D-galactopyranoside
IUPAC Name(2R,3R,4R,5R,6R)-5-azido-2-(hydroxymethyl)-6-(4-nitrophenoxy)oxane-3,4-diol
Molecular FormulaC₁₂H₁₄N₄O₇
Molecular Weight326.26
InChIInChI=1S/C12H14N4O7/c13-15-14-9-11(19)10(18)8(5-17)23-12(9)22-7-3-1-6(2-4-7)16(20)21/h1-4,8-12,17-19H,5H2/t8-,9-,10+,11-,12+/m1/s1
SMILESC1=CC(=CC=C1[N+](=O)[O-])OC2C(C(C(C(O2)CO)O)O)N=[N+]=[N-]
CAS No: 210418-04-5 MDL No: MFCD00270053 Chemical Formula: C12H14N4O7 Molecular Weight: 326.26


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