Para-Lacto-N-hexaose Analogue (Para-LNH)

Para-Lacto-N-hexaose (Para-LNH, also known as pLNH or para-lacto-N-hexaose, CAS 64331-48-2) is a hexasaccharide human milk oligosaccharide (HMO) analogue distinguished by its linear type-1 and type-2 chain architecture: Galβ1-3GlcNAcβ1-3(Galβ1-4GlcNAcβ1-6)Galβ1-4Glc, featuring a branched para-LacNAc motif without fucosylation or sialylation found in native HMOs. This structure mimics complex poly-N-acetyllactosamine (poly-LacNAc) extensions on glycoproteins, serving as a research tool to study bifidogenic selectivity, pathogen decoy functions, and glycan-lectin interactions in neonatal nutrition. Present in trace amounts in human milk (<0.1% total HMOs) but abundant in bovine/porcine milks, Para-LNH supports Bifidobacterium longum subsp. infantis growth via sequential β-galactosidase/β-N-acetylhexosaminidase digestion, while resisting most enteric pathogens due to lacking blood group epitopes. Chemically synthesized via iterative glycosylation, it aids HMO structural libraries, LC-MS standards for milk glycomics, and prebiotic fortification testing for infant formulas targeting microbiome maturation and anti-adhesive protection against necrotizing enterocolitis (NEC). Its neutral, non-sialylated nature enables precise dissection of branching effects on sialidase resistance and galectin binding, with applications in glycotherapy for inflammatory bowel disease and cancer glycan engineering.

Appearance

• White to off-white amorphous lyophilized powder.
• Non-hygroscopic solid, stable under ambient conditions.​

Source

• Trace in human milk; abundant in bovine colostrum and porcine milk.
• Fully chemoenzymatic synthesis using β1-3/β1-4 galactosyltransferases on lacto-N-triose acceptors.​

Molecular Weight and Structure

• Formula: C40H68N2O31; MW 1072.96 g/mol.
• Galβ1→3GlcNAcβ1→3[Galβ1→4GlcNAcβ1→6]Galβ1→4Glc (branched para-type 1/2 chains).

Sugar Specificity

• Neutral type-1/2 LacNAc branches selective for B. infantis ABC-transporter uptake.
• Binds galectin-3 weakly; resistant to fucosidases/sialidases.​

Biological Activity

• Bifidogenic: 2-4 fold growth promotion of B. longum subsp. infantis vs. Bacteroides.
• Anti-adhesive: Mild inhibition of EPEC type-1 pili (IC50 >10 mM).​

Purity and Microbial Contamination

• ≥90-98% by NMR/HPAEC for research grades.
• Endotoxin <0.1 EU/mg; sterile processing <10 CFU/g total count.​

Identity and Quality Control

• 1H-NMR (anomeric β-Gal ~4.4-4.6 ppm), HRMS (m/z 1073 [M+H]+).
• Enzymatic sequencing (β1-3/4 galactosidases), monosaccharide HPLC.​

Shelf Life and Storage

• 3+ years at -20°C lyophilized; solutions stable 1 month at 4°C.
• Desiccated, light-protected; single-use aliquots recommended.​

Applications

• HMO glycomics standards; prebiotic screening for synbiotics.
• Glycobiology: poly-LacNAc probes, infant formula R&D.

Key Characteristics

• Highly water-soluble (>200 mg/mL); neutral branched hexasaccharide.
• Bifido-selective, metabolically stable analogue.​

Citation Links

• https://pubchem.ncbi.nlm.nih.gov/compound/71308411​
• https://pubchem.ncbi.nlm.nih.gov/compound/194173​
• https://www.elicityl-oligotech.com/human-milk-oligosaccharides-hmo/1164-para-lacto-n-hexaose-para-lnh-90-nmr.html​
• https://pmc.ncbi.nlm.nih.gov/articles/PMC11370726/​
• https://www.bioglyco.com/para-lacto-ini-hexaose-item-6525.html​
• https://pubchem.ncbi.nlm.nih.gov/compound/22833594​
• https://bovinedb.ca/metabolites/BMDB0006628​
• https://cymitquimica.com/cas/64309-00-8/​
• https://glyconnect.expasy.org/hmo/structures​
• https://pmc.ncbi.nlm.nih.gov/articles/PMC9235823/