1,3,4-Tri-O-acetyl-2-deoxy-2-fluoro-L-fucose

1,3,4-Tri-O-acetyl-2-deoxy-2-fluoro-L-fucose is a synthetic analog of L-fucose, a biologically important deoxy sugar found in mammalian glycoconjugates and bacterial cell walls. The compound features a fluorine atom at the 2-position, replacing the hydroxyl group, and acetyl protecting groups on hydroxyls at positions 1, 3, and 4. The fluorine substitution alters the electronic and steric environment of the sugar, affecting how it interacts with enzymes and receptors. Acetyl groups serve as temporary protecting groups to enable selective modifications or controlled glycosylation. This compound is widely used in chemical glycobiology to study L-fucosidases (enzymes that cleave L-fucose) and to design potent inhibitors that mimic enzymatic transition states. Additionally, it is valuable for synthesizing modified oligosaccharides and glycoconjugates with modified biological functions relevant to cell signaling and immune responses.

IUPAC Name 

• Methyl ((2S,3S,4R,5R)-3,4-bis(acetyloxy)-5-(acetoxymethyl)-2-fluorotetrahydrofuran)

Appearance

• Typically a colorless to white crystalline solid or powder

Source

• Synthesized from L-fucose or related chiral precursors
• Multistep synthesis involving deoxygenation, fluorination at C2, and acetylation of hydroxyl groups

Molecular Weight and Structure

• Molecular Weight: 292.26 g/mol
• Molecular Formula: C12H17FO7
• Six-membered L-fucose ring
• Fluorine atom at C2 replacing hydroxyl
• Acetyl groups at 1, 3, and 4 positions; methyl at C6
• Opposite stereochemistry at chiral centers compared to D-enantiomer

Sugar Specificity

• Modified sugar building block without inherent sugar-binding specificity
• Specificity arises when incorporated into larger glycoconjugates with L-fucose recognition

Biological Activity

• May inhibit L-fucosidases by mimicking enzymatic transition states
• Influences binding affinity of glycosides and oligosaccharides toward receptors and enzymes for L-fucose

Purity and Microbial Contamination

• High purity (>95%) essential for synthesis and biological studies
• Purity verified by chromatography and NMR
• Microbial contamination not a concern except for biological applications needing sterility testing

Identity and Quality Control

• Confirmed by ^1H, ^13C, ^19F NMR spectroscopy and mass spectrometry
• Quality control includes purity checks, absence of impurities, water content (Karl Fischer), optical rotation with opposite sign to D-enantiomer

Shelf Life and Storage

• Stable for years when stored dry, protected from moisture, light, air, under inert atmosphere at refrigerated temperatures

Application

• Potent inhibitors for L-fucosidases
• Mechanistic studies of L-fucosidase enzyme action
• Building block for synthesis of modified oligosaccharides with L-fucose
• Used in glycoconjugate synthesis (glycoproteins, glycolipids)
• Chemical glycobiology and probe development for L-fucose biology

Key Characteristics

• Fluorinated L-sugar analog with acetyl protecting groups
• Potent L-fucosidase inhibitor
• Versatile building block for oligosaccharide and glycoconjugate synthesis
• Stable under proper storage
• Soluble in common organic solvents (chloroform, DCM, ethyl acetate)

Citation

• “Synthesis of 2-deoxy-2-fluoro-L-fucose”
• “L-fucosidase inhibitors 2-fluoro-L-fucose”
• “Mechanism of L-fucosidases 2-fluoro-L-fucose”
• “Glycosylation reactions 2-fluoro L-fucose glycosyl donors”
• “Synthesis of fluorinated L-carbohydrates”
• “Carbohydrate-based enzyme inhibitors fluorine L-fucose”
• “Transition state mimics glycosidases fluorine L-fucose”
• “Fluorinated carbohydrates biological activity L-fucose”
• “Synthesis of modified carbohydrates L-fucosidase inhibitors”
• “Fluorinated L-sugar analogs”