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/