Methyl α-L-fucopyranoside

Methyl α-L-fucopyranoside is a methylated glycoside derivative of L-fucose, where the hydroxyl group at the anomeric position of L-fucose is replaced by a methoxy group, forming a stable α-glycosidic bond. This compound is a white crystalline powder with a molecular structure that closely mimics natural L-fucose in its pyranose form. It is widely used in glycobiology and synthetic carbohydrate chemistry as a model compound to study the roles of fucose-containing glycans in biological processes, including cell-cell recognition, immune modulation, and microbial adhesion. Methyl α-L-fucopyranoside serves as a valuable intermediate in the synthesis of oligosaccharides and glycomimetics, aiding in drug discovery and therapeutic developments targeting fucose-dependent pathways. It is provided with high purity and is utilized in diverse biochemical and medicinal chemistry applications.

IUPAC Name

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

Appearance

• White crystalline solid

Source

• Synthesized chemically from L-fucose by methylation at the anomeric hydroxyl position

Molecular Weight and Structure

• Molecular formula: C7H14O5
• Molecular weight: 178.18 g/mol
• Structure: Pyranose ring with methoxy substitution at the anomeric carbon; L-configuration of fucose
• SMILES: CO[C@@H]1OC@HC@HC@H[C@H]1O

Sugar Specificity

• Methyl α-glycoside of L-fucose, specific to L-fucose metabolic and glycosylation pathways
• Recognized by lectins and enzymes targeting L-fucose residues

Biological Activity

• Functions as a mimic of natural L-fucosylated glycans involved in immune recognition and cellular communication
• Used in studies on pathogen binding, immune cell adhesion, and enzyme specificity
• Acts as a molecular tool for drug design targeting fucose-binding proteins

Purity and Microbial Contamination

• Typically ≥95% purity confirmed by HPLC or NMR
• Chemical-grade with negligible microbial contamination
• Supplied with Certificates of Analysis for research-grade use

Identity and Quality Control

• Verified by NMR spectroscopy, mass spectrometry, and chromatography
• Melting point and optical rotation consistent with methyl α-L-fucopyranoside
• Strict quality control and documentation provided

Shelf Life and Storage

• Store in a cool, dry place at 2–8 °C
• Stable for at least 1-2 years under proper conditions
• Protect from moisture and light exposure

Application

• Used in glycobiology for studying fucosylation-dependent biological interactions
• Precursor in synthetic carbohydrate chemistry for constructing fucosylated oligosaccharides
• Utilized in drug discovery as part of glycomimetic design
• Analytical reagent for lectin and enzyme assays involving fucose recognition

Key Characteristics

• Methylated L-fucose glycoside in pyranose form
• CAS number 14687-15-1
• Molecular weight 178.18 g/mol, white crystalline solid
• High purity, suitable for biochemical and medicinal research
• Mimics natural L-fucosylated glycans for biological studies
• Stable under refrigerated storage with appropriate handling
• Verified by extensive spectral and chromatographic analyses
• Supports molecular biology, synthetic chemistry, immunology, and drug development
• Recognized in lectin-binding and enzyme-substrate interactions

Citation 

• ChemicalBook Methyl α-L-fucopyranoside
• Sigma-Aldrich catalog
• GlpBio product data
• GoldBio biochemical reagent info
• PubChem molecular data
• MedChemExpress product info
• ChemImpex catalog and research applications
• PMC glycobiology research articles
• Zoro research compound listing
• RSC Organic & Biomolecular Chemistry