2-Deoxy-2-fluoro-L-fucose

2-Deoxy-2-fluoro-L-fucose

2-Deoxy-2-fluoro-L-fucose (CAS No: 70763-62-1) is a fluorinated analog of the naturally occurring sugar L-fucose. It is a white to off-white crystalline solid with a molecular formula of C6H11FO4 and a molecular weight of 166.15 g/mol. The compound is characterized by the replacement of the hydroxyl group at the 2-position of L-fucose with a fluorine atom, making it a 2-deoxy-2-fluoro derivative.

Chemically, 2-Deoxy-2-fluoro-L-fucose is soluble in solvents like dimethylformamide (DMF), dimethyl sulfoxide (DMSO), ethanol, and phosphate-buffered saline (PBS, pH 7.2). It is typically stored at -20 °C to maintain stability. The compound’s pKa is predicted to be around 12.7.

Biologically, 2-Deoxy-2-fluoro-L-fucose functions as a potent inhibitor of protein fucosylation by blocking the synthesis of GDP-fucose, a donor substrate essential for fucosyltransferase enzymes. This inhibition affects glycoprotein fucosylation, important in cell signaling, adhesion, and immune function. Because of these properties, it has potential uses in cancer treatment and immunotherapy by interfering with tumor progression and enhancing immune responses.

It is also used in biochemical research to study glycosylation pathways and develop therapeutic agents targeting fucosylation-related processes.

Summary of key details:

This compound plays a crucial role in inhibiting fucosylation and is valuable in biomedical research and therapeutic development.pubchem.ncbi.nlm.nih+5