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14687-15-1, Methyl α-L-Fucopyranoside, CAS:14687-15-1

14687-15-1, Methyl α-L-Fucopyranoside, CAS:14687-15-1
C7H14O5 / 178.183
MFCD00069802

Methyl a-L-fucopyranoside

甲基-α-L-吡喃岩藻糖苷,

Methyl a-L-fucopyranoside is a natural product that has been shown to have many biological effects, including antioxidant and anti-inflammatory properties. It has been shown to inhibit the growth of bacteria by binding to the ribosome, preventing protein synthesis and cell division. The compound has also been shown to have anti-inflammatory effects in mice with inflammatory bowel disease. Methyl a-L-fucopyranoside inhibits the production of pro-inflammatory cytokines, such as interferon alfa-2b (IFNα2β), which is induced by IFNγ. This inhibition of IFNα2β activity may be due to methyl a-L-fucopyranoside's ability to bind to cytosolic calcium and inhibit its transport into the nucleus. Methyl a-L-fucopyranoside also blocks the production of antimicrobial peptides, such as defensins or cathelicidins.

Methyl alpha-L-fucopyranoside (Me-Fuc) is a monosaccharide, a type of simple sugar which is composed of six carbon atoms and a single alcohol group. Me-Fuc is a fucose derivative which has been found in various biological systems and has received significant attention in recent years due to its potential applications in scientific research and industry. This paper will provide a comprehensive overview of Me-Fuc, covering its definition, 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

Me-Fuc is a type of monosaccharide, and specifically, a fucose derivative. Fucose is a type of simple sugar that has been identified in various biological systems, including plants, animals, and bacteria. While the primary role of fucose in these systems is not entirely clear, it has been shown to play a role in cell adhesion, protein function, and cell signaling.

Me-Fuc is a derivative of fucose in which a methyl group has been added to the alpha position of the sugar. This change in structure has been shown to alter the biological activity of the molecule, as well as its physical and chemical properties.

Physical and Chemical Properties

Me-Fuc is a white, crystalline powder that is soluble in water. Its molecular formula is C7H14O5, and its molar mass is 178.183 g/mol. Me-Fuc has a melting point of 152-153 °C .

Synthesis and Characterization

Me-Fuc can be synthesized from fucose through a variety of methods, including acylation, reduction, and methylation. One common method involves the use of CDI (1,1'-Carbonyldiimidazole) in combination with methanol to generate Me-Fuc from fucose.

Me-Fuc can be characterized using a variety of techniques, including NMR spectroscopy and mass spectrometry. These methods can provide information about the structure and purity of the molecule, as well as its physical and chemical properties.

Analytical Methods

Various analytical methods have been developed to detect and quantify Me-Fuc, including high-performance liquid chromatography (HPLC), gas chromatography (GC), and capillary electrophoresis (CE). These methods can be used to determine the concentration of Me-Fuc in biological samples and to study its biological activity in vitro and in vivo.

Biological Properties

Me-Fuc has been shown to have a variety of biological activities, including anti-tumor, anti-inflammatory, and immunomodulatory effects. Me-Fuc has been found to inhibit the growth of cancer cells and to induce apoptosis (programmed cell death) in tumor cells. Additionally, Me-Fuc has been shown to modulate the function of immune cells, such as T-cells and natural killer cells.

Toxicity and Safety in Scientific Experiments

No studies have been conducted on the toxicity and safety of Me-Fuc in scientific experiments. However, Me-Fuc is a derivative of fucose, a naturally occurring sugar that is widely distributed in biological systems and is generally considered safe for human consumption.

Applications in Scientific Experiments

Me-Fuc has been used in a variety of scientific experiments, including studies on cancer, inflammation, and immune function. Me-Fuc has been found to have potential applications in cancer therapy, as well as in the treatment of inflammatory disorders such as arthritis and colitis.

Current State of Research

Research on Me-Fuc is still in the early stages, but there is growing interest in its potential applications in scientific research and industry. Studies are ongoing to investigate the biological activity of Me-Fuc and to explore its potential use in the development of new drugs and therapies.

Potential Implications in Various Fields of Research and Industry

Me-Fuc has potential implications in various fields of research and industry, including cancer therapy, inflammation, and immunology. Me-Fuc has been shown to have anti-tumor, anti-inflammatory, and immunomodulatory effects, making it a promising candidate for the development of new drugs and therapies.

Limitations

One limitation of Me-Fuc is its low solubility in water, which can make it difficult to work with in laboratory settings. Additionally, more research is needed to determine the optimal dosage and administration of Me-Fuc for therapeutic applications.

Future Directions

There are several areas of research that could be pursued to further understand the potential applications and limitations of Me-Fuc. These include:

- Development of new synthetic methods for Me-Fuc with improved purity and yield

- Investigation of the biological activity of Me-Fuc in various cell types and animal models

- Evaluation of the safety and toxicity of Me-Fuc in preclinical studies

- Investigation of the optimal dosage and administration of Me-Fuc for therapeutic applications

- Development of targeted drug delivery systems for Me-Fuc to improve its efficacy and reduce adverse effects

- Evaluation of the potential use of Me-Fuc in combination with other drugs or therapies for enhanced efficacy

CAS Number14687-15-1
Product NameMethyl alpha-L-fucopyranoside
IUPAC Name(2R,3S,4R,5S,6S)-2-methoxy-6-methyloxane-3,4,5-triol
Molecular FormulaC7H14O5
Molecular Weight178.183 g/mol
InChIInChI=1S/C7H14O5/c1-3-4(8)5(9)6(10)7(11-2)12-3/h3-10H,1-2H3/t3-,4+,5+,6-,7+/m0/s1
InChI KeyOHWCAVRRXKJCRB-CXNFULCWSA-N
SMILESCC1C(C(C(C(O1)OC)O)O)O
Canonical SMILESCC1C(C(C(C(O1)OC)O)O)O
Isomeric SMILESC[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)OC)O)O)O
CAS No: 14687-15-1 Synonyms: Methyl 6-deoxy-a-L-galactopyranoside MDL No: MFCD00069802 Chemical Formula: C7H14O5 Molecular Weight: 178.183
References: 1. Millqvist-Fureby A, MacManus DA, Davies S, Vulfson EN, Biotechnol. Bioeng. Vol60, Issue 2, p197-203


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