LNFP III

Lacto-N-fucopentaose III (LNFP III, Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1-4Glc)  constitutes a fucosylated type 2 chain human milk oligosaccharide representing 2-5% of total HMOs in secretor mothers' milk, manifesting as a white amorphous powder essential for neonatal immune modulation and Lewis X antigen research. This sialyl-Lewis X precursor features the Lewis X determinant [Galβ1-4(Fucα1-3)GlcNAc] on LNnT core, exhibiting ultra-high affinity for E-selectin (leukocyte rolling KD 0.5-2 μM), P-selectin, and DC-SIGN while blocking norovirus GII.10/rotavirus (>88% inhibition) and Campylobacter jejuni adhesion through competitive receptor mimicry; selectively metabolized by Bifidobacterium infantis fucosidase AfcB, it reduces experimental autoimmune encephalomyelitis (EAE) severity by 60%, ameliorates Gulf War Illness hippocampal deficits, induces tolerogenic dendritic cells via Aldh1a2/Ido1 upregulation, and serves as gold standard Le^x pentasaccharide for cancer glycomimetics and selectin inhibitor screening with gastric stability pH 2-10, >650 g/L solubility, and 60-month lyophilized shelf life. Appearance White amorphous powder; odorless, hygroscopic. Water solubility >650 g/L; clear solutions pH 6-8. ​ Source 2-5% total HMOs in secretor mothers' mature milk. α1-3 fucosyltransferase on lacto-N-neotetraose (LNnT). ​ Molecular Weight and Structure 853.77 g/mol, formula C₃₂H₅₅NO₂₅ (CAS 25541-09-7). Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1-4Glc; Lewis X-type HMO. ​ Sugar Specificity B. infantis AfcB fucosidase (Km 0.25 mM); E/P-selectin ligands. Norovirus/rotavirus receptor mimic; DC-SIGN high affinity. ​ Biological Activity Reduces EAE severity 60%; Gulf War Illness hippocampal repair. ​ Induces tolerogenic DCs (Aldh1a2↑, Ido1↑); Bifido-selective. ​ Purity and Microbial Contamination ≥95% HPLC/NMR; LNnT <1%, Le^x isomers <0.5%. Endotoxins <10 EU/mg; research/GMP sterile. ​ Identity and Quality Control ¹H-NMR Fucα1-3 H1 5.10 ppm (d, J=3.7 Hz); LC-MS [M+Na]⁺ 876.4. HPAEC Fuc:Gal:GlcNAc:Glc 1:2:1:1; [α]D -5° to +2°. ​ Shelf Life and Storage 60 months -20°C lyophilized; 36 months 4°C desiccated. N₂ sealed; <60% RH prevents anomeric shifts. ​ Applications Immune modulator; EAE/MS therapeutics; selectin inhibitors. Le^x cancer biomarker standards; HMO research. ​ Key Characteristics Lewis X (Leˣ) pentasaccharide prototype; tolerogenic glycan. Ultra-high E-selectin avidity; gastric/pancreatic stable. ​ Citation Links https://www.chemsrc.com/en/cas/25541-09-7_752737.html ​ https://pubchem.ncbi.nlm.nih.gov/compound/53477857 ​ https://www.medchemexpress.com/lacto-n-fucopentaose-iii.html ​ https://pubchem.ncbi.nlm.nih.gov/compound/14130796 ​ https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0289111.htm ​ https://hmdb.ca/metabolites/HMDB0006576 ​ https://www.elicityl-oligotech.com/.../5125-lacto-n-fucopentaose-iii... ​ https://contaminantdb.ca/contaminants/CHEM036149 ​ https://glycosmos.org/structure/LNFP-III ​ https://www.cd-bioglyco.com/lacto-n-fucopentaose-iii ​