Methyl β-D-fucopyranoside

Methyl β-D-fucopyranoside is a methylated derivative of the naturally occurring sugar D-fucose, where the hydroxyl group at the anomeric carbon is replaced by a methoxy group, forming a stable glycosidic bond. This compound exists as a white to almost white crystalline powder and is widely used in glycobiology and carbohydrate chemistry research as a model compound to study fucose-related carbohydrate-protein interactions. It plays a significant role in investigating cellular processes involving fucosylation, such as cell signaling, immune responses, and pathogen recognition. Additionally, methyl β-D-fucopyranoside serves as a precursor and building block in synthetic carbohydrate chemistry, facilitating the design of glycomimetics and glycoprotein analogs for drug discovery and therapeutic applications. Its biological importance stems from fucose’s presence in many cell surface glycans, making this methyl glycoside a valuable analytical and synthetic tool in biochemistry and molecular biology.​​

IUPAC Name

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

Appearance

• White to almost white crystalline powder​

Source

• Chemically synthesized from D-fucose via methylation reactions
• Also obtainable through enzymatic modification of natural substrates​

Molecular Weight and Structure

• Molecular formula: C7H14O5
• Molecular weight: 178.18 g/mol​
• Structure: Pyranose ring form of D-fucose with a methoxy group replacing the anomeric hydroxyl (methyl glycoside)
• SMILES: C[C@H]1C@@HC@HC@@HC@HO1​

Sugar Specificity

• A fucose analog with methylation at the anomeric position
• Recognized by fucose-specific lectins and enzymes, useful for studying fucosylation pathways​

Biological Activity

• Exhibits roles in carbohydrate-protein interactions due to mimicking natural fucose glycosides
• Used in studies on immune system modulation, cell adhesion, and pathogen recognition through fucosylated glycans
• Potential precursor in synthesizing bioactive glycomimetics and therapeutic agents​

Purity and Microbial Contamination

• Purity typically ≥95-98% as assessed by HPLC or GC
• Chemically synthesized compound with negligible microbial contamination
• Supplied with Certificates of Analysis verifying chemical purity​

Identity and Quality Control

• Verified by NMR spectroscopy, mass spectrometry, and chromatographic methods
• Melting point around 123 °C
• Optical rotation and spectral data consistent with molecular structure
• Standards provided for identity confirmation​

Shelf Life and Storage

• Recommended storage at 2–8 °C in a dry, dark environment
• Stable for 1–2 years depending on conditions
• Protect from moisture and direct light exposure​

Application

• Model compound in fucosylation and glycobiology research
• Intermediate for chemical synthesis of fucosylated oligosaccharides
• Used in drug design for targeting carbohydrate-binding proteins
• Employed in analytical assays involving fucose-specific enzymes and lectins
• Ingredient in cosmetic and food industry for its natural sugar properties​

Key Characteristics

• Methylated glycoside of D-fucose in pyranose form
• CAS number 24332-98-7
• White crystalline powder with molecular weight 178.18 g/mol
• High purity ≥95% with reliable quality control data
• Useful in biochemical and medicinal research related to fucose biology
• Stable under refrigerated conditions with 1-2 year shelf life
• Widely applied in synthetic glycoscience and carbohydrate-protein interaction studies
• Verified by comprehensive spectral and chromatographic analyses
• Compatible with enzymatic and chemical glycosylation assays
• Supports development of novel therapeutics and biomolecular probes

Citation 

• ChemicalBook: Methyl Beta-L-Fucopyranoside​
• PubChem molecular data​
• Sigma-Aldrich related compounds​
• DrugBank chemical identifiers​
• GlpBio product info​
• GoldBio Beta-D-Fucoside info​
• PMC articles on methyl glycosides​
• Synthose chemical intermediates​
• ChemImpex research product details​
• ScienceDirect glycoscience topics​