5-Bromo-4-chloro-3-indolyl a-D-fucopyranoside

5-Bromo-4-chloro-3-(a-D-fucopyranosyloxy)indole; X-a-D-Fucoside

This powerful chromogenic substrate is designed specifically for the assay and detection of a-L-fucosidase enzyme activity. With a unique combination of bromo, chloro, and indolyl moieties, it offers enhanced stability and promotes color development that is unparalleled in clarity and intensity. Ideal for biochemistry, molecular biology, and related life sciences applications, this substrate provides unmatched performance and reliability for all your a-L-fucosidase enzyme research needs.

5-Bromo-4-chloro-3-indoxyl-alpha-D-fucopyranoside: An Overview of Properties, Synthesis, Analytical Methods, Biological Properties, Applications, and Future Directions

Definition and Background:

5-Bromo-4-chloro-3-indoxyl-alpha-D-fucopyranoside is a synthetic, chromogenic substrate that is commonly used in the biochemical and pharmaceutical industries. It is often abbreviated as X-Fuc or XBF. This compound is composed of indoxyl, fucose, and two halogens (bromine and chlorine). 5-Bromo-4-chloro-3-indoxyl-alpha-D-fucopyranoside is frequently used to study the enzymatic activity of glycosidases, which are involved in glycoprotein degradation, and it has also been used to identify mutations in Fabry disease.

Physical and Chemical Properties:

5-Bromo-4-chloro-3-indoxyl-alpha-D-fucopyranoside is a blue to purple solid, which is soluble in water, methanol, and dimethyl sulfoxide (DMSO). It has a melting point of 220-225 °C and a boiling point of 661.7 °C at 760 mmHg. Its molecular formula is C16H17BrClNO6, and it has a molecular weight of 446.66 g/mol.

Synthesis and Characterization:

5-Bromo-4-chloro-3-indoxyl-alpha-D-fucopyranoside can be synthesized through the reaction of 5-bromo-4-chloro-3-indoxyl with alpha-D-fucose, using either sulfuric acid or triflic acid as a catalyst. The resulting compound can be purified through column chromatography or recrystallization. The synthesized compound can be characterized using various analytical techniques, including nuclear magnetic resonance (NMR) spectroscopy and high-performance liquid chromatography (HPLC).

Analytical Methods:

5-Bromo-4-chloro-3-indoxyl-alpha-D-fucopyranoside can be detected and quantified using various analytical methods such as HPLC, ultraviolet-visible (UV-Vis) spectroscopy, liquid chromatography-mass spectrometry (LC-MS), and capillary electrophoresis (CE).

Biological Properties:

5-Bromo-4-chloro-3-indoxyl-alpha-D-fucopyranoside is enzymatically cleaved by fucosidases, which are responsible for the hydrolysis of alpha-L-fucosidic bonds in glycoproteins. It has been used to identify and measure the activity of various fucosidases, including alpha-L-fucosidase and alpha-L-fucoside 1-sulfatase.

Toxicity and Safety in Scientific Experiments:

There is limited information available on the toxicity and safety of 5-Bromo-4-chloro-3-indoxyl-alpha-D-fucopyranoside. However, it is recommended to handle this compound with caution, and to follow standard laboratory safety protocols.

Applications in Scientific Experiments:

5-Bromo-4-chloro-3-indoxyl-alpha-D-fucopyranoside has many applications in scientific experiments. It is commonly used as a substrate to study fucosidase enzymatic activity, and as a tool for identifying glycoprotein mutations in various diseases. Additionally, it can be used for the detection and quantification of fucose-containing glycoproteins.

Current State of Research:

Research on 5-Bromo-4-chloro-3-indoxyl-alpha-D-fucopyranoside is ongoing, and new applications and discoveries related to this compound continue to emerge. Recent research has focused on the use of this compound as a diagnostic tool for Fabry disease, and for identifying new therapeutic targets for other diseases that involve fucose-containing glycoproteins.

Potential Implications in Various Fields of Research and Industry:

The use of 5-Bromo-4-chloro-3-indoxyl-alpha-D-fucopyranoside has potential implications in various fields of research and industry, including biochemistry, pharmaceuticals, and diagnostics. This compound can be used in the development of new therapies for diseases that involve fucose-containing glycoproteins, and it can also be used in the detection and quantification of these glycoproteins for diagnostic purposes.

Limitations and Future Directions:

Although 5-Bromo-4-chloro-3-indoxyl-alpha-D-fucopyranoside has many applications, there are also some limitations to its use. For example, it has a relatively short shelf life and must be stored properly to maintain its stability. Additionally, future research could focus on identifying new enzymatic activities for this compound, as well as developing new synthesis methods to increase its efficiency and stability.

Some potential future directions for research on 5-Bromo-4-chloro-3-indoxyl-alpha-D-fucopyranoside include:

- Developing new applications for this compound as a diagnostic tool for other diseases that involve fucose-containing glycoproteins

- Investigating the role of fucose-containing glycoproteins in cancer and other diseases

- Exploring the use of this compound in drug discovery and development, particularly for diseases that involve fucose-containing glycoproteins

- Developing new analytical methods for the detection and quantification of fucose-containing glycoproteins using 5-Bromo-4-chloro-3-indoxyl-alpha-D-fucopyranoside as a substrate

- Investigating the potential for using this compound in the development of biosensors for biomedical applications.

In conclusion, 5-Bromo-4-chloro-3-indoxyl-alpha-D-fucopyranoside is a versatile compound that has many applications in the biochemical and pharmaceutical industries. Its ability to identify and measure the activity of fucosidase enzymes, as well as identify glycoprotein mutations in various diseases, makes it a valuable tool for research and development. Ongoing research will continue to explore the many potential applications of this compound, and future studies will shed light on its potential limitations and expand its use in various fields.