2-Deoxy-2-fluoro-D-fucose

2-Deoxy-2-fluoro-D-fucose

2-Deoxy-2-fluoro-D-fucose is a fluorinated derivative of the sugar D-fucose, characterized by the substitution of a fluorine atom at the 2-position instead of the hydroxyl group. This alteration makes it a useful analog for glycosylation studies and biochemical research involving fucose metabolism and enzyme inhibition. The compound is typically a white crystalline solid.

The molecular formula of 2-Deoxy-2-fluoro-D-fucose is C6H11FO4, with a molecular weight of approximately 166.15 g/mol. It demonstrates good solubility in solvents such as dimethylformamide (DMF), dimethyl sulfoxide (DMSO), ethanol, and phosphate-buffered saline (PBS). The compound is generally stored at low temperatures (0 to 8 °C) to maintain stability.

Biochemically, 2-Deoxy-2-fluoro-D-fucose acts as an inhibitor of fucosylation, a key post-translational modification implicated in multiple biological processes including cell signaling, adhesion, and immune response. The fluorinated sugar is metabolized intracellularly to inhibit fucosyltransferase enzymes by competing with natural GDP-fucose substrates. This property is of interest for therapeutic applications such as cancer treatment and immunomodulation.

Physicochemical and safety data for 2-Deoxy-2-fluoro-D-fucose are similar to those of its L-isomer counterpart but specific stereochemistry is important in biological contexts.

Summary of key details:

This compound has growing importance in biomedical research targeting glycosylation pathways and cancer therapeutics.chemicalbook+2