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​