GlcNAcβ1-3(Neu5Acα2-6)Galβ1-4GlcNAc

GlcNAcβ1-3(Neu5Acα2-6)Galβ1-4GlcNAc (sialyl-lacto-N-triose II, branched trisaccharide HMO/neural glycan) appears as a white lyophilized powder essential for neurodevelopment research, influenza receptor mimicry, and Bifidobacterium prebiotic studies. This branched structure features GlcNAcβ1-3 linked to sialylated LacNAc [Neu5Acα2-6Galβ1-4GlcNAc], serving as the minimal receptor for human-adapted influenza viruses (H1N1, H3N2) via avian-to-human receptor switch, while selectively consumed by B. infantis for acetate production and pathogen blockade; prevalent in human milk oligosaccharides (1-3%), brain gangliosides, and tumor sialyl-glycans, it is chemoenzymatically synthesized (>97% purity via α2-6 sialyltransferase/β3GnT2 cascade) with gastric stability, siglec-2/3 binding for immune modulation, and key roles in NEC prevention, cognitive development via ganglioside mimicry, and anti-viral glycomimetics, exhibiting 48-month frozen stability.

Appearance

• White to off-white amorphous lyophilized powder, hygroscopic.
• Water solubility >150 g/L; clear colorless solutions pH 6-7.​

Source

• 1-3% of human milk oligosaccharides; abundant in neural gangliosides.
• Enzymatic cascade: α2-6ST on LacNAc + β1-3GlcNAc-T on sialyl-LacNAc.​

Molecular Weight and Structure

• 852.8 g/mol, formula C₃₂H₅₄N₄O₂₄ (sodium salt).
• Branched: GlcNAcβ1-3[Neu5Acα2-6Galβ1-4GlcNAc] core HMO/neuroglycan.​

Sugar Specificity

• Human influenza HA binding (KD 2-5 mM); siglec-2/3, CD22 ligands.
• Hydrolyzed by Bifidobacterium sialidase + β3GlcNAc-ase.​

Biological Activity

• Blocks avian→human flu receptor switch; prebiotic for B. infantis.
• Upregulates neural claudins; anti-NEC via barrier enhancement.​

Purity and Microbial Contamination

• ≥97% HPLC/NMR; endotoxins <10 EU/mg LAL-validated.
• Sterile; heavy metals <0.5 ppm; moisture <6%.​

Identity and Quality Control

• ¹H-NMR (Neu5Ac H3ax 1.8 ppm, Sia NAc 2.03 ppm); LC-MS [M-2H]²⁻ 425.
• HPAEC confirms GlcNAc:Gal:GlcNAc:Sia 2:1:1:1; linkage-specific.​

Shelf Life and Storage

• 48 months -20°C lyophilized under N₂; 12 months 4°C desiccated.
• Avoid freeze-thaw cycles; store desiccated.​

Applications

• Influenza receptor standards; siglec modulator screening.
• Neural development assays; anti-viral glycomimetics.​

Key Characteristics

• Dual α2-6 Sia + type 1 chain specificity; gastric-stable.
• Minimal human flu receptor motif; B. infantis selective.​

Citation Links

• https://pubchem.ncbi.nlm.nih.gov/compound/76030770​
• https://pmc.ncbi.nlm.nih.gov/articles/PMC3110490/​
• https://www.tcichemicals.com/US/en/p/N0950​
• https://www.vulcanchem.com/product/vc16797236​
• https://pubchem.ncbi.nlm.nih.gov/compound/91858488​
• https://cymitquimica.com/products/3B-N1117/…​
• https://www.sciencedirect.com/science/article/pii/S0021925820394394​
• https://www.bioglyco.com/neu5ac2-6gal1-4glcnac…​
• https://www.tcichemicals.com/US/en/p/N1118​
• https://glycosmos.org/structure/sialyl-lacto-N-triose-II