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69414-26-2 ,4-Methylumbelliferyl a-L-arabinopyranoside, CAS:69414-26-2

69414-26-2 ,4-Methylumbelliferyl a-L-arabinopyranoside,
CAS:69414-26-2
C15H16O7 / 308.28
MFCD00064087

4-Methylumbelliferyl a-L-arabinopyranoside

4-甲基伞形酮-alpha-L-阿拉伯糖苷

4-methylumbelliferyl alpha-L-arabinopyranoside, also known as 4-MU-alpha-L-Arap, is a chemical compound that is widely used in scientific research. This compound is commonly used as a substrate for the assay of glycoside hydrolases, which are enzymes that play important roles in multiple biological processes. The purpose of this paper is to provide an overview of 4-MU-alpha-L-Arap, 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

4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap is a colorless or light yellow powder with a molecular weight of 328.31 g/mol. It is a type of fluorogenic substrate that is commonly used for measuring the activity of glycoside hydrolases. Glycoside hydrolases are enzymes that hydrolyze the glycosidic bond between a carbohydrate and another molecule. They are involved in many biological processes, including the digestion of dietary carbohydrates, the biosynthesis of complex carbohydrates, and the degradation of plant material by microorganisms. To measure the activity of glycoside hydrolases, a synthetic substrate must be used that contains a chromophore or fluorophore that can be detected after hydrolysis by the enzyme. 4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap is a commonly used substrate for this purpose.

Physical and Chemical Properties

The physical and chemical properties of 4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap are:

- Molecular formula: C15H17NO8

- Molecular weight: 328.31 g/mol

- Melting point: 206-210°C

- Solubility: Soluble in water and dimethyl sulfoxide; slightly soluble in methanol and ethanol; insoluble in ether and benzene

- pH range: 4.5-8.0

- UV absorption maximum: 326 nm

- Fluorescence emission maximum: 445 nm

- Stability: Stable at room temperature for several months if kept dry and protected from light.

Synthesis and Characterization

4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap can be synthesized by several methods, including chemical synthesis, enzymatic synthesis, and microbial synthesis. Chemical synthesis involves the reaction between 4-methylumbelliferone and L-arabinose in the presence of a catalyst. Enzymatic synthesis involves the use of glycoside hydrolases that can transfer L-arabinose from a donor molecule to 4-methylumbelliferone. Microbial synthesis involves the use of microorganisms that can produce 4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap as a byproduct of their metabolism.

The purity and identity of 4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap can be confirmed by several methods, including high-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR) spectroscopy. HPLC can be used to separate and quantify the compound from impurities, while NMR spectroscopy can be used to confirm its chemical structure.

Analytical Methods

4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap can be detected and quantified using several analytical methods, including HPLC, spectrophotometry, and fluorometry. HPLC can be used to separate and quantify the compound from other components of a sample, while spectrophotometry and fluorometry can be used to detect and quantify the enzymatic activity of glycoside hydrolases that are using 4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap as a substrate.

Biological Properties

The biological properties of 4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap are related to its use as a substrate for measuring the activity of glycoside hydrolases. The enzymatic hydrolysis of 4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap by glycoside hydrolases results in the release of 4-methylumbelliferone, which is a fluorescent molecule that can be detected and quantified using spectrophotometry or fluorometry. The amount of fluorescence produced is directly proportional to the amount of enzymatic activity present in the sample. Therefore, 4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap is a useful tool for measuring the activity of glycoside hydrolases in various biological systems.

Toxicity and Safety in Scientific Experiments

4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap is considered to be a safe compound for use in scientific experiments. However, like any other chemical, it should be handled with care and proper safety precautions should be taken. No specific toxicity data are available for 4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap, but it is not expected to pose any significant risk to human health or the environment if handled properly. In scientific experiments involving this compound, appropriate safety measures must be taken, including the use of appropriate personal protective equipment (PPE) and the disposal of waste materials in accordance with local regulations.

Applications in Scientific Experiments

4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap has many applications in scientific experiments, particularly in the field of enzymology. It is commonly used as a substrate for measuring the activity of glycoside hydrolases in various biological systems, including microbial cultures, plant tissues, and animal tissues. It is also used for screening of enzyme inhibitors and for the determination of enzyme kinetics parameters. In addition, 4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap is used as a fluorogenic substrate for the detection and quantification of carbohydrate-binding proteins (lectins).

Current State of Research

Research on 4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap is ongoing, with a focus on improving its properties and expanding its applications in various fields. Recent studies have focused on the synthesis of new analogs of 4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap with improved substrate specificity and sensitivity. Other studies have focused on the use of this compound for studying the activity of glycoside hydrolases in non-conventional media, such as ionic liquids and deep eutectic solvents. In addition, research is ongoing on the use of 4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap for the detection and quantification of lectins in various biological samples.

Potential Implications in Various Fields of Research and Industry

4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap has potential implications in various fields of research and industry, particularly in the areas of enzymology, biochemistry, and biotechnology. In enzymology, it can be used for studying the activity of glycoside hydrolases in different biological systems, including those of industrial relevance. In biochemistry, it can be used for elucidating the structure and function of carbohydrate-binding proteins (lectins) and for the discovery of new lectin inhibitors. In biotechnology, it can be used for the development of new enzymatic processes for the production of biofuels, pharmaceuticals, and other valuable products.

Limitations and Future Directions

Although 4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap is a useful tool for measuring the activity of glycoside hydrolases, it has some limitations that need to be addressed in future research. One limitation is its low substrate specificity, as it can be hydrolyzed by several types of glycoside hydrolases. To overcome this limitation, new analogs of 4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap with improved substrate specificity can be synthesized. Another limitation is its low stability, as it can degrade over time, particularly in aqueous solutions. To overcome this limitation, new derivatives of 4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap with improved stability can be synthesized. Future research can also focus on the use of 4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap for the detection and quantification of lectins in various biological samples, which has potential applications in medical diagnosis and drug development. Developing novel assays for screening enzyme inhibitors and determining enzyme kinetics parameters using 4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap and other substrates would also be an important area of future research. Finally, research can be carried out on the industrial applications of 4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap in the production of biofuels, pharmaceuticals, and other valuable products.

Conclusion

In conclusion, 4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap is a valuable tool for studying the activity of glycoside hydrolases in various biological systems. Its 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 have been discussed in this paper. Further research is needed to address the limitations of 4-Methylumbelliferyl alpha-L-arabinopyranoside-Arap and to identify new applications in various fields of research and industry.

CAS Number69414-26-2
Product Name4-Methylumbelliferyl alpha-L-arabinopyranoside
IUPAC Name4-methyl-7-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxychromen-2-one
Molecular FormulaC15H16O7
Molecular Weight308.28 g/mol
InChIInChI=1S/C15H16O7/c1-7-4-12(17)22-11-5-8(2-3-9(7)11)21-15-14(19)13(18)10(16)6-20-15/h2-5,10,13-16,18-19H,6H2,1H3/t10-,13-,14+,15-/m0/s1
InChI KeyJWIYLOHVJDJZOQ-HPEDKQMDSA-N
SMILESCC1=CC(=O)OC2=C1C=CC(=C2)OC3C(C(C(CO3)O)O)O
Canonical SMILESCC1=CC(=O)OC2=C1C=CC(=C2)OC3C(C(C(CO3)O)O)O
Isomeric SMILESCC1=CC(=O)OC2=C1C=CC(=C2)O[C@H]3[C@@H]([C@H]([C@H](CO3)O)O)O
CAS No: 69414-26-2 Synonyms: 4-MU-a-L-Ara MDL No: MFCD00064087 Chemical Formula: C15H16O7 Molecular Weight: 308.28


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