Lacto-N-fucopentaose I (LNFP I)

Lacto-N-fucopentaose I (LNFP I, Fucα1-2Galβ1-3GlcNAcβ1-3Galβ1-4Glc) constitutes a core fucosylated human milk oligosaccharide (HMO) abundant in secretor mothers’ milk (~5-10% total HMOs), appearing as a white lyophilized powder essential for neonatal antiviral defense and Bifidobacterium-directed gut colonization. This type 1 chain pentasaccharide features the H-antigen (Fucα1-2Gal) on LNT core, serving as high-affinity ligand for E-/L-selectins (leukocyte rolling), DC-SIGN (dendritic cell targeting), and norovirus GII.4 capsid VP1 (viral adsorption blocker >85%); selectively hydrolyzed by B. longum subsp. infantis fucosidase AfcA while resisting Bacteroides, it upregulates Reg3γ/Paneth cell maturation, inhibits Campylobacter/ETEC adhesion 80-95%, reduces NEC by 65%, and supports cognitive development via ganglioside mimicry, with GRAS status, gastric stability (pH 2.5-9), >600 g/L solubility, and 48-month shelf life ideal for infant formula and anti-infective therapeutics.

Appearance

• White to off-white amorphous hygroscopic powder.​
• Highly water-soluble >600 g/L; clear solutions pH 6-8.​

Source

• 5-10% total HMOs in secretor mothers’ mature milk.​
• Enzymatic fucosylation (α1-2FucT) of lacto-N-tetraose (LNT).​

Molecular Weight and Structure

• 853.77 g/mol, formula C₃₂H₅₅NO₂₅ (CAS 7578-25-8).
• Fucα1-2Galβ1-3GlcNAcβ1-3Galβ1-4Glc H-type 1 pentasaccharide.​

Sugar Specificity

• B. infantis AfcA fucosidase (Km 0.3 mM); E/L-selectin ligands.​
• Norovirus VP1 blocker; DC-SIGN binding motif.​

Biological Activity

• Inhibits norovirus adsorption >85% via VP1 blockade.​
• Amplifies B. longum growth 4x; Reg3γ/Paneth induction.​

Purity and Microbial Contamination

• ≥98% HPLC/NMR; LNT <1%, mono-fucose <0.5%.​
• Endotoxins <10 EU/mg; GMP-grade sterile.​

Identity and Quality Control

• ¹H-NMR Fucα1-2 H1 5.12 ppm; LC-MS [M+Na]+ 876.4.​
• HPAEC Fuc:Gal:GlcNAc:Glc 1:2:1:1; optical rotation +25°.​

Shelf Life and Storage

• 48 months -20°C lyophilized; 24 months 4°C desiccated.​
• Hygroscopic—N₂ sealed, <50% RH.​

Applications

• Infant formula HMO (0.8-2 g/L); antiviral synbiotics.​
• Selectin inhibitor screening; NEC therapeutics.​

Key Characteristics

• H-antigen type 1 specificity; potent norovirus blocker.​
• Dual immune/modulatory roles; gastric-stable.​

Citation Links

• https://pubchem.ncbi.nlm.nih.gov/compound/53477883​
• https://pubchem.ncbi.nlm.nih.gov/compound/50909802​
• https://www.medchemexpress.com/lacto-n-fucopentaose-i.html​
• https://www.glpbio.com/lacto-n-fucopentaose-i.html​
• https://contaminantdb.ca/contaminants/CHEM036200​
• https://foodb.ca/compounds/FDB024034​
• https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5763416.htm​
• https://www.glyxera.com/product/lnfp-i/​
• https://gsrs.ncats.nih.gov/ginas/app/beta/substances/Q6AD5JR2NN​
• https://www.sigmaaldrich.com/US/en/product/ambeedinc/ambh9ad23f0f​