Methyl β-L-fucopyranoside

Methyl β-L-fucopyranoside is a methylated derivative of the natural sugar L-fucose, characterized by the substitution of the anomeric hydroxyl group of L-fucopyranose with a methoxy group, forming a stable glycoside. This compound exists as a white crystalline powder and is widely used in biochemical and synthetic carbohydrate research for studying fucosylation pathways and carbohydrate-protein interactions. Its structure mimics that of natural fucosides, allowing it to be a valuable tool in the design of glycomimetics, the understanding of cell signaling mechanisms, and the development of pharmaceutical agents targeting fucose-recognizing proteins. Methyl β-L-fucopyranoside has been employed in studies related to immune modulation, bacterial adhesion, and enzyme substrate specificity. The compound is supplied with high purity and strict quality controls, making it suitable for research in molecular biology, glycobiology, and medicinal chemistry.​

IUPAC Name

• (2S,3S,4R,5S,6S)-2-methoxy-6-methyloxane-3,4,5-triol​

Appearance

• White to almost white crystalline powder​

Source

• Chemically synthesized from L-fucose through methylation of the anomeric hydroxyl group
• Can also be derived enzymatically via glycosylation reactions​

Molecular Weight and Structure

• Molecular Formula: C7H14O5
• Molecular Weight: 178.18 g/mol​
• Structure: Pyranose ring of L-fucose with a methyl group at anomeric carbon; stable glycosidic bond formation
• SMILES: CO[C@H]1OC@@HC@@HC@@H[C@@H]1O​

Sugar Specificity

• L-fucose derivative with methylation at C1, maintaining fucose specificity
• Widely recognized in fucose-binding protein interactions​

Biological Activity

• Involved in carbohydrate-protein interaction studies relevant to immune response and microbial adhesion
• Useful in investigating cellular adhesion, lectin binding, and development of fucose-based inhibitors
• Precursor for glycomimetic drugs targeting fucose-mediated pathways​

Purity and Microbial Contamination

• Purity ≥95% typically confirmed by HPLC or NMR
• Microbial contamination negligible due to chemical synthesis and quality controls
• Supplied with Certificates of Analysis ensuring purity and identity​

Identity and Quality Control

• Verified by NMR, mass spectrometry, and chromatographic techniques
• Melting Point: ~123 °C
• Optical rotation and spectral data consistent with methyl β-L-fucopyranoside
• Supplied with detailed quality certificates​

Shelf Life and Storage

• Recommended storage at 2-8 °C away from moisture and light
• Stable under appropriate conditions for 1-2 years
• Keep in tightly sealed containers​

Application

• Used to study glycosylation and fucosylation in biochemical and cell biology research
• Intermediate for synthesis of fucosylated oligosaccharides and glycoconjugates
• Employed in drug design to create inhibitors of fucose-binding lectins and enzymes
• Analytical reagent in glycobiology for fucose recognition studies​

Key Characteristics

• Methylated glycoside of L-fucose in the pyranose form
• High purity and well-characterized for research use
• CAS number 24332-98-7
• White crystalline powder with molecular weight 178.18 g/mol
• Stable storage and reliable spectral identity
• Important tool for glycoscience, medicinal chemistry, and immunology
• Recognized by fucose-specific proteins and lectins
• Supports synthesis and study of glycomimetic compounds

Citation

• ChemicalBook: Methyl beta-L-fucopyranoside​
• Sigma-Aldrich product info​
• PubChem molecular data​
• DrugBank chemical info​
• J-GLOBAL chemical substance information​
• GoldBio product overview​
• MedChemExpress glycoscience reagent​
• ChemImpex catalog and purity data​
• Zoro research compound catalog​
• PMC article on fucosylated molecules and their biological interaction​