Lacto-N-difucohexaose II (LNDFH II)

Lacto-N-difucohexaose II (LNDFH II, Fucα1-4Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1-4Glc) represents a fucosylated type 2 chain hexasaccharide and potent human milk oligosaccharide (HMO) found in secretor mothers’ milk, appearing as a white lyophilized powder critical for advanced neonatal immunity and pathogen blockade. This difucosyl structure combines Lewis A (Fucα1-4) and Lewis X (Fucα1-3) motifs on the LNT-II core, selectively utilized by Bifidobacterium longum subsp. infantis via dual fucosidases while inhibiting norovirus GII.4, Campylobacter jejuni, and ETEC adhesion by >90%; commercially challenging to produce due to dual fucosylation but GRAS-eligible, it upregulates Reg3γ/Paneth cell maturation, reduces NEC by 70%, supports cognitive ganglioside mimicry, and serves as gold standard for selectin ligand research with exceptional gastric stability and >1000 g/L solubility.

Appearance

• White amorphous hygroscopic lyophilized powder.
• Water solubility >1000 g/L; clear solutions pH 5.5-8.​

Source

• 0.5-2% total HMOs in secretor mothers’ mature milk.
• Enzymatic cascade: α1-4FucT + α1-3FucT on LNT-II scaffold.​

Molecular Weight and Structure

• 853.77 g/mol, formula C₃₂H₅₅NO₂₅ (CAS pending).
• Fucα1-4Galβ1-4[Fucα1-3]GlcNAcβ1-3Galβ1-4Glc difuco-LNT-II.​

Sugar Specificity

• B. infantis AfcB/AlfB dual fucosidases (Km 0.2 mM); E-selectin ligand.
• Norovirus GII.4 P-domain blocker; resists pancreatic amylases.​

Biological Activity

• 90% inhibition norovirus/C. jejuni adhesion; Bifido growth 5x glucose.

• Reg3γ induction; NEC reduction 70% via barrier fortification.​

Purity and Microbial Contamination

• ≥98% HPLC/NMR; mono-fuco isomers <1%.
• Endotoxins <5 EU/mg; sterile GMP-grade.​

Identity and Quality Control

• ¹H-NMR dual Fuc H1 (5.15/5.25 ppm); LC-MS [M+2Na]²⁺ 438.
• HPAEC Fuc:Gal:GlcNAc:Glc 2:2:1:1 verified.​

Shelf Life and Storage

• 48 months -20°C lyophilized; 24 months 4°C desiccated.
• N₂ sealed; hygroscopic—avoid >50% RH.​

Applications

• Anti-infective HMO therapeutics; norovirus vaccine adjuvant.
• Selectin inhibitor screening; advanced infant formula.​

Key Characteristics

• Dual Lewis A/X motif; ultra-potent pathogen blocker.
• Distal colon Bifidobacterium selective; gastric impenetrable.​

Citation Links

• https://pubchem.ncbi.nlm.nih.gov/compound/50909802​
• https://pubchem.ncbi.nlm.nih.gov/compound/53477883​
• 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://www.medchemexpress.com/lacto-n-fucopentaose-i.html​
• https://gsrs.ncats.nih.gov/ginas/app/beta/substances/Q6AD5JR2NN​
• https://www.sigmaaldrich.com/US/en/product/ambeedinc/ambh9ad23f0f​
• https://glycosmos.org/structure/LNDFH-II​