GlcNAcβ1-3Galβ1-4GlcNAc

GlcNAcβ1-3Galβ1-4GlcNAc (lacto-N-triose II, LNT-II) represents a core type 2 chain trisaccharide and essential building block for complex N-glycans, appearing as a white lyophilized powder widely utilized in glycan synthesis, lectin binding studies, and human milk oligosaccharide research. This linear structure serves as the acceptor for fucosyltransferases (forming Le^x) and sialyltransferases (forming sialyl-LacNAc), abundant in human milk (5-10% total HMOs), neural gangliosides, tumor-associated glycans, and leukocyte selectin ligands; chemoenzymatically produced via β3GnT-β4GalT cascades (>98% purity), it demonstrates gastric stability with selective Bifidobacterium longum utilization for acetate/butyrate production, key roles in NEC prevention, cognitive development via ganglioside mimicry, cancer biomarker screening, and functional food prebiotics, exhibiting excellent solubility (>400 g/L) and multi-year desiccated stability.

Appearance

• White amorphous lyophilized powder, odorless and non-hygroscopic.
• Highly water-soluble (>400 g/L); forms clear solutions pH 6-8.​

Source

• 5-10% human milk oligosaccharides; abundant in N-glycans, gangliosides.
• Biosynthetic via β1-3 N-acetylglucosaminyltransferase on LacNAc.​

Molecular Weight and Structure

• 551.5 g/mol, formula C₂₁H₃₆N₂O₁₆ (sodium salt).
• Linear: GlcNAcβ1-3Galβ1-4GlcNAc type 2 chain trisaccharide.​

Sugar Specificity

• Precursor for Le^x (FucT), sialyl-LacNAc (ST3/6Gal); DC-SIGN ligand.
• Hydrolyzed by Bacteroides β3GlcNAc-ase + β4-galactosidase.​

Biological Activity

• Prebiotic for Bifidobacterium longum subsp. infantis; barrier enhancement.
• Core scaffold for sLeX tumor antigens; anti-inflammatory.​

Purity and Microbial Contamination

• ≥98% HPLC/NMR purity; endotoxins <10 EU/mg LAL-tested.
• Sterile filtered; heavy metals <1 ppm; moisture <5%.​

Identity and Quality Control

• ¹H-NMR (β-GlcNAc H1 4.72 ppm, Gal H1 4.45 ppm); LC-MS [M+Na]⁺ 574.3.
• HPAEC-PAD Gal:GlcNAc 1:2 ratio; anomeric purity >99%.​

Shelf Life and Storage

• 60 months -20°C lyophilized; 36 months ambient desiccated.
• N₂ atmosphere; avoid >70% RH.​

Applications

• HMO synthesis scaffold; glycan microarray standards.
• Selectin ligand research; cancer biomarker assays.​

Key Characteristics

• Linear type 2 chain acceptor; gastric-resistant.
• Universal scaffold for fucosylation/sialylation.​

Citation Links

• https://pubchem.ncbi.nlm.nih.gov/compound/91855153​
• https://www.bioglyco.com/gal1-4glcnac1-3gal1-4glcnac1-3gal1-4glcnac-item-14140.html​
• https://pmc.ncbi.nlm.nih.gov/articles/PMC4672149/​
• https://www.sciencedirect.com/science/article/pii/S0021925819597149​
• https://www.chemicalbook.com/ChemicalProductProperty_EN_CB12604564.htm​
• https://www.tcichemicals.com/p/G0494​
• https://www.chemsrc.com/en/cas/81520-71-0_324131.html​
• https://glycosmos.org/structure/lacto-N-triose-II​
• https://pubchem.ncbi.nlm.nih.gov/compound/GlcNAc-beta1-3-Gal-beta1-4-GlcNAc​
• https://resources.amsbio.com/Datasheets/300261-1.pdf​