Chemical Identity
- IUPAC Name (α-L-fucopyranose): (2R,3S,4R,5S,6S)-6-methyloxane-2,3,4,5-tetrol
- IUPAC Name (β-L-fucose): 6-deoxy-β-L-galactopyranose
- IUPAC Name (open-chain): (2S,3R,4R,5S)-2,3,4,5-tetrahydroxyhexanal
- Synonyms: L-fucose, L-fucopyranose, 6-deoxy-L-galactose, L-galactomethylose, 6-deoxy-L-galactopyranose, isodulcit, rhodeose, α-L-fucose, β-L-fucose, fucopyranose
- CAS Number: 2438-80-4
- Molecular Formula: C₆H₁₂O₅
- Molecular Weight: 164.16 g/mol (average); 164.06847 Da (monoisotopic)
- SMILES (α-L-fucopyranose): C[C@@H]1OC@@HC@@HC@H[C@@H]1O
- SMILES (β-L-fucose): C[C@@H]1OC@HC@@HC@H[C@@H]1O
- InChI (α-L-fucopyranose): InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6+/m0/s1
- InChIKey: SHZGCJCMOBCMKK-SXUWKVJYSA-N (α-L-fucopyranose)
- ChEBI ID: 2181 (L-fucose); 42589 (β-L-fucose)
- PubChem CID: 17106
- KEGG Compound ID: C01019
- PDB Ligand Code: FUC (α-L-fucopyranose)
- DrugBank ID: DB04473 (α-L-fucose); DB03283 (β-L-fucose)
Physical Properties
| Property | Value |
|---|---|
| Physical State | White crystalline solid |
| Melting Point | 140 °C (experimental); 150–153 °C (lit.) |
| Boiling Point | 399.1 ± 35.0 °C at 760 mmHg |
| Flash Point | 209.3 ± 22.4 °C |
| Density | 1.4 ± 0.1 g/cm³ |
| Water Solubility | 827 g/L (ALOGPS); 985 mg/mL; 0.1 g/mL H₂O, clear, colorless |
| LogP (XLogP3-AA) | −2.1 |
| Vapor Pressure | 0.0 ± 2.1 mmHg at 25 °C |
| Refractive Index | 1.531 |
Computed Chemical Properties
| Property | Value |
|---|---|
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 0 |
| Topological Polar Surface Area | 90.2 Ų |
| Heavy Atom Count | 11 |
| Formal Charge | 0 |
| Complexity | 139 |
| Defined Atom Stereocenter Count | 4 |
| Undefined Atom Stereocenter Count | 1 |
| Covalently-Bonded Unit Count | 1 |
| pKa (Strongest Acidic) | 11.3 |
| pKa (Strongest Basic) | −3.6 |
| Physiological Charge | 0 |
| Refractivity | 34.38 m³·mol⁻¹ |
| Polarizability | 15.21–15.35 ų |
Collision Cross Section (CCS)
| Value | Method |
|---|---|
| 147.32 Ų [M+Na]⁺ | DT; stepped-field |
| 138.7 Ų [M+Na]⁺ | DT; single field calibrated with ESI Low Concentration Tuning Mix (Agilent) |
| 144.6 Ų [M+Na]⁺ | DT; single field calibrated with Agilent tune mix |
| 138.6 Ų [M+Na]⁺ | Unified CCS Compendium |
| 146.4 Ų [M+Na]⁺ | Unified CCS Compendium |
Spectral Information
Mass Spectrometry (GC-MS) – Top 5 Peaks
| m/z (relative intensity) | Instrument |
|---|---|
| 117.0 (100), 147.0 (16.0), 118.0 (10.3), 103.0 (9.8), 89.0 (8.8) | GC-EI-TOF (Leco Pegasus IV) |
| 117.0 (100), 147.0 (14.6), 160.0 (11.1), 118.0 (10.7), 131.0 (6.9) | GC-EI-TOF (Leco Pegasus IV) |
Mass Spectrometry (LC-MS/MS) – Top 5 Peaks
| m/z (relative intensity) | Instrument |
|---|---|
| 101.0 (100), 69.0 (89.6), 89.0 (41.6), 87.0 (28.9), 100.0 (12.9) | Quattro_QQQ, positive |
| 69.0 (100), 101.0 (34.1), 73.0 (27.8), 87.0 (26.7), 89.0 (14.5) | Quattro_QQQ, positive |
Mass Spectrometry (Other MS) – Top 5 Peaks
| Precursor m/z | Mode | Top Peaks |
|---|---|---|
| 164.11 | ESI positive, QqQ/MS | 82 (100) |
| 163.061 [M−H]⁻ | Orbitrap, negative | 101.023 (100), 71.013 (86.9), 142.992 (84.4), 73.028 (81.9), 162.893 (77.2) |
NMR and IR: ¹H NMR, ¹³C NMR, FTIR (KBr wafer), ATR-IR, and FT-Raman spectra are available via SpectraBase and MoNA.
Structural Classification
- Type: Deoxy sugar; hexose monosaccharide
- Ring Form: Pyranose (six-membered ring)
- Configuration: L-configuration (levorotatory); the only L-sugar commonly utilized by mammals
- Anomers: α-L-fucopyranose and β-L-fucopyranose
- Key Structural Features: Lacks a hydroxyl group at the C-6 position (6-deoxy); L-configuration distinguishes it from D-sugars
Biological Role and Occurrence
- Fucose is a common component of N-linked and O-linked glycans, glycolipids, and glycoproteins in mammalian cells.
- It is the fundamental subunit of fucoidan polysaccharides found in seaweed.
- It plays a role in ABO blood group antigen determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions.
- Fucose is metabolized by α-fucosidase.
- It is a metabolite found in Escherichia coli (strain K12, MG1655) and in mice and humans.
- Free L-fucose in serum and urine has been investigated as a potential marker for cancer, cirrhosis, alcoholic liver disease, and gastric ulcers.
Biosynthesis and Metabolism
- GDP-L-fucose biosynthesis pathway: L-Fucose → GDP-L-Fucose (enzymes: EC 1.1.1.122, 2.7.1.52, 3.2.1.51, 3.2.1.63, 5.3.1.3, 5.3.1.25)
- KEGG Pathways: Fructose and mannose metabolism (map00051); Amino sugar and nucleotide sugar metabolism (map00520); Metabolic pathways (map01100); Microbial metabolism in diverse environments (map01120); Biosynthesis of nucleotide sugars (map01250); Two-component system (map02020); Quorum sensing (map02024); C-type lectin receptor signaling pathway (map04625)
Safety and Regulatory Information
- GHS Classification: Not classified as hazardous by 13 of 14 reporting companies (92.9% of reports).
- Hazard Statements: May cause irritation (Sigma-Aldrich MSDS).
- Cosmetic Ingredient Review: Found safe in present practices of use and concentration.
- EPA TSCA Status: Active.
- WGK Germany: 3
- HS Code: 2912491000
Clinical Information
- Under investigation in clinical trial NCT03354533 (Study of ORL-1F (L-fucose) in patients with Leukocyte Adhesion Deficiency Type II).
- Maximum drug development phase: Phase 3 (ChEMBL).
References
- PubChem CID 17106 (L-Fucose). National Center for Biotechnology Information.
- ChEBI: 2181 (L-fucose); 42589 (β-L-fucose). European Bioinformatics Institute.
- KEGG Compound C01019 (L-Fucose). Kanehisa Laboratories.
- RCSB PDB Ligand FUC (alpha-L-fucopyranose). Research Collaboratory for Structural Bioinformatics.
- ECMDB (E. coli Metabolome Database) entries ECMDB20264 and M2MDB006329.
- Becker, D.J. & Lowe, J.B. (2003). "Fucose: biosynthesis and biological function in mammals." Glycobiology, 13(7):41R-53R.
- IUPHAR/BPS Guide to Pharmacology Ligand ID: 4721.
