2-Deoxy-2-fluoro-L-fucose

2-Deoxy-2-fluoro-L-fucose (2FF) is a fluorinated analog of the natural sugar L-fucose, where the hydroxyl group at position 2 is replaced by a fluorine atom. This subtle chemical modification enables it to act as a potent inhibitor of fucosylation, a critical enzymatic process that attaches fucose to glycoproteins and glycolipids involved in cell signaling, adhesion, and immune regulation. By competitively inhibiting fucosyltransferases and reducing the biosynthesis of GDP-fucose, the donor substrate for fucosylation, 2FF disrupts normal fucose incorporation into glycoconjugates. This property makes it invaluable in biomedical research, especially for probing glycosylation pathways and studying diseases such as cancer and inflammatory disorders. 2FF also shows promise in enhancing immunotherapy efficacy by modifying antibody-dependent cellular cytotoxicity (ADCC) through afucosylated antibodies. The compound is chemically synthesized and applied in vitro and in vivo to explore fucosylation-related biological functions and potential therapeutic interventions.

IUPAC Name

• (2S,3R,4R,5S)-2-fluoro-3,4,5-trihydroxyhexanal
• (3S,4R,5S,6S)-3-fluoro-6-methyltetrahydropyran-2,4,5-triol (alternate)

Appearance

• White crystalline solid

Source

• Chemically synthesized fluorinated analog of L-fucose

Molecular Weight and Structure

• Molecular formula: C6H11FO4
• Molecular weight: 166.15 g/mol
• Structure: Fluorine substitution at carbon-2 of a hexose sugar ring typical of fucose
• Canonical SMILES: CC@HC@@HC@@HC@HC=O

Sugar Specificity

• Specifically targets fucose metabolic and enzymatic pathways due to structural similarity with L-fucose
• Acts as a competitive inhibitor in fucosylation processes

Biological Activity

• Potent inhibitor of fucosyltransferases (FUTs)
• Blocks de novo synthesis of GDP-fucose by cellular enzymes
• Suppresses fucosylation of glycoproteins and glycolipids in cells
• Used to modulate immune responses and cancer cell growth
• Enhances antibody-dependent cellular cytotoxicity by generating afucosylated antibodies
• Demonstrated anti-tumor activity via immune modulation and direct inhibition of tumor growth pathways

Purity and Microbial Contamination

• Chemical purity: ≥98% (usually by HPLC or 1H-NMR)
• Microbial contamination testing not generally applicable for pure chemical standards
• Supplied with Certificates of Analysis to verify purity and identity

Identity and Quality Control

• Verified by NMR, mass spectrometry, and HPLC methods
• Pure compound with melting point approximately 172-174 °C
• Quality confirmed by structural elucidation using SMILES, InChI, and molecular formula data
• Provided with safety documentation including SDS and GHS hazard classifications

Shelf Life and Storage

• Shelf life: Typically 12–24 months when stored properly
• Storage conditions: Store at 2–8 °C (refrigerated) or -20 °C for longer preservation
• Protect from light and moisture
• Avoid repeated freeze-thaw cycles for dissolved solutions

Application

• Widely used as a biochemical tool to inhibit fucosylation in laboratory studies
• Used in cancer and immunology research to study glycosylation-dependent signaling pathways
• Investigated for therapeutic potential in oncology to improve checkpoint inhibitor efficacy
• Tool compound for biochemical characterization of fucosylation in glycoprotein function and cell biology

Key Characteristics

• Fluorinated L-fucose analog with a fluorine at the 2-position
• CAS number 70763-62-1
• White crystalline solid, molecular weight 166.15 g/mol
• Selective competitive inhibitor of fucosyltransferases and GDP-fucose biosynthesis
• High chemical purity ≥98% with robust identity confirmation methods
• Stable under refrigerated or frozen storage conditions for extended shelf life
• Used in cancer, immune modulation, and glycoscience research
• Potent anti-fucosylation biological activity with immunomodulatory effects
• Enhances antibody cytotoxicity by producing afucosylated antibodies
• Valuable tool to investigate glycosylation-dependent biological processes and potential therapies

Citation 

• Sigma-Aldrich 2-Deoxy-2-fluoro-L-fucose Product
• Synthose 2-Deoxy-2-fluoro-L-fucose Datasheet
• PharmaAffiliates CAS and chemical info
• MedChemExpress Fucosylation Inhibitor
• PubChem 2-Fluorofucose Details
• Nature – Fucosylation Inhibition in Cancer
• ACS Publications on fluorinated fucose derivatives
• NCBI PMC on Fucosylated molecule inhibition
• Google Patents – Cancer Treatment Using 2FF
• XcessBio Shelf life and storage data