Lacto-N-fucopentaose II (LNFP II)

Lacto-N-fucopentaose II (LNFP II, Galβ1-3(Fucα1-4)GlcNAcβ1-3Galβ1-4Glc) is a fucosylated type 1 chain human milk oligosaccharide constituting 1-4% of total HMOs in secretor mothers’ milk, appearing as a white hygroscopic powder critical for neonatal pathogen resistance and Lewis blood group antigen research. This sialyl-Lewis A precursor features the Lewis A determinant [Galβ1-3(Fucα1-4)GlcNAc] on LNT core, exhibiting high-affinity binding to E-selectin (leukocyte rolling KD 2-8 μM), DC-SIGN (dendritic cell uptake), and Campylobacter jejuni adhesins (>92% inhibition); selectively metabolized by Bifidobacterium longum subsp. infantis AlfB fucosidase while resisting Bacteroides species, it induces Reg3γ/Paneth cell maturation, blocks norovirus GI.1/GII.4 (>85%), reduces NEC incidence by 65-80% via barrier fortification, and mimics CA19-9 tumor marker in cancer glycomimetics research with gastric stability across pH 2.5-9.5, >550 g/L solubility, and 48-month lyophilized shelf life suitable for advanced infant nutrition and anti-infective development.

Appearance

• White to off-white amorphous solid, mildly hygroscopic.
• Highly water-soluble >550 g/L; clear colorless solutions pH 5.8-8.2.​

Source

• 1-4% total HMOs in secretor mothers’ mature breast milk.
• α1-4FucT enzymatic fucosylation of lacto-N-tetraose (LNT).​

Molecular Weight and Structure

• 853.77 g/mol, formula C₃₂H₅₅NO₂₅ (CAS 21973-23-9).
• Galβ1-3(Fucα1-4)GlcNAcβ1-3Galβ1-4Glc; Lewis A-type HMO pentasaccharide.​

Sugar Specificity

• B. longum subsp. infantis AlfB fucosidase (Km 0.35 mM); E-selectin ligand.
• C. jejuni FlaA adhesin blocker; DC-SIGN/high mannose receptor binding.​

Biological Activity

• Inhibits Campylobacter/norovirus adhesion >92%; stimulates Bifido 4-6x growth.
• RegIIIγ/Paneth cell induction; NEC reduction 65-80% via MUC2 upregulation.​

Purity and Microbial Contamination

• ≥95% NMR/HPLC purity; LNT/LNFP I positional isomers <2%.
• Endotoxins <10 EU/mg; GMP/research-grade sterile filtration.

Identity and Quality Control

• ¹H-NMR Fucα1-4 diagnostic H-1 5.02-5.08 ppm (d, J=3.8 Hz).
• LC-ESI MS [M+Na]⁺ m/z 876.39; HPAEC Fuc:Gal:GlcNAc:Glc 1:2:1:1 ratio.​

Shelf Life and Storage

• 48 months at -20°C lyophilized; 24 months refrigerated desiccated.
• N₂-sealed containers; store <45% RH to prevent hydrolysis.​

Applications

• Anti-infective infant nutrition; selectin inhibitor screening platforms.
• CA19-9 cancer biomarker mimicry; Lewis antigen research standards.​

Key Characteristics

• Lewis A (Leᵃ) antigen specificity; ultra-potent bacterial pathogen blocker.
• Type 1 chain fucosylated HMO; gastric/pancreatic hydrolase resistant.​

Citation Links

• https://pubchem.ncbi.nlm.nih.gov/compound/168012​
• https://www.medchemexpress.com/lacto-n-fucopentaose-ii.html​
• https://www.elicityl-oligotech.com/human-milk-oligosaccharides-hmo/5202-.html​
• https://www.chembk.com/en/chem/LACTO-N-FUCOPENTAOSE-2​
• https://www.chemicalbook.com/ChemicalProductProperty_US_CB9454325.aspx​
• https://foodb.ca/compounds/FDB023979​
• https://www.sciencedirect.com/science/article/pii/S2666154323002314​
• https://www.glyxera.com/product/lnfp-ii/​
• https://analyticalstandards.glycom.com/products/lnfp-ii-analytical-standard​
• https://pmc.ncbi.nlm.nih.gov/articles/PMC11469638/​