GalNAcβ1-4Galβ1-4GlcNAc

GalNAcβ1-4Galβ1-4GlcNAc (N-acetylgalactosaminyl-lacto-N-biose II, blood group CAD trisaccharide precursor) constitutes a core type 2 chain structure in mucin-type O-glycans and selectin ligands, synthesized as white lyophilized powder for cancer biomarker research and glycan engineering applications. This trisaccharide features β-GalNAc capping the LacNAc (Galβ1-4GlcNAc) disaccharide, serving as substrate for core 1 synthase (T-synthase) extension to T/Tn antigens while inhibiting α2-3 sialylation; prevalent in gastric mucins, tumor-associated carbohydrates (TACs), and porcine gastric mucin, it binds macrophage galectin-3 and DC-SIGN with high avidity, modulating immune evasion and metastasis; chemoenzymatically produced (>98% purity via β4GalNAc-T1 transferase), it exhibits gastric stability, selective Bifidobacterium galactosidase hydrolysis, and key roles in CAD blood group phenotyping, anti-cancer glycomimetics, and functional food prebiotics, with proven 5-year shelf life stability.

Appearance

• White to off-white amorphous lyophilized powder, odorless.
• Highly water-soluble (>250 g/L); stable clear solutions pH 5-8.

Source

• Abundant in porcine gastric mucin, human tumor mucins (stomach/colon).
• Biosynthetic via β1-4GalNAc transferase on LacNAc acceptors.

Molecular Weight and Structure

• 623.57 g/mol, formula C₂₄H₄₁N₃O₁₈ (sodium salt).
• β-D-Gal pNAc-(1→4)-β-D-Gal p-(1→4)-β-D-Glc pNAc linear trisaccharide.

Sugar Specificity

• Binds galectin-3, DC-SIGN, MGL via terminal GalNAc; precursor for sialyl-T.
• Hydrolyzed by β-N-acetylhexosaminidase from Bacteroides ovatus.

Biological Activity

• Inhibits E-selectin rolling; modulates tumor immune evasion via Mφ gal-3.
• Prebiotic stimulating Akkermansia muciniphila growth and mucin production.

Purity and Microbial Contamination

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

Identity and Quality Control

• ¹H-NMR (NAc 2.05 ppm, GalNAc H1 4.65 ppm β); LC-ESI MS [M+Na]⁺ 646.
• HPAEC-PAD confirms GalNAc:Gal:GlcNAc 1:1:1; anomeric purity >99%.

Shelf Life and Storage

• 60 months at -20°C lyophilized; 24 months ambient desiccated.
• Avoid >70% RH to prevent Maillard reactions.

Applications

• CAD blood group typing; tumor mucin biomarker assays.
• Selectin inhibitor screening; mucin glycoengineering scaffolds.

Key Characteristics

• Core 1 synthase substrate; GalNAc transferase specificity.
• Type 2 chain scaffold for tumor antigen extension; gastric-stable.

Citation Links

• https://pubchem.ncbi.nlm.nih.gov/compound/46906084
• https://pmc.ncbi.nlm.nih.gov/articles/PMC4672149/
• https://www.sciencedirect.com/science/article/pii/S0021925819597149
• https://febs.onlinelibrary.wiley.com/doi/10.1016/S0014-5793(99)01629-4][6]
• https://www.chemimpex.com/products/42347
• https://www.chemicalbook.com/ChemicalProductProperty_EN_CB02526003.htm
• https://pubchem.ncbi.nlm.nih.gov/compound/91854621
• https://glycosmos.org/structure/GalNAc-b1-4-Gal-b1-4-GlcNAc
• https://www.cd-bioglyco.com/galnac-beta1-4-gal-beta1-4-glcnac
• https://www.tcichemicals.com/US/en/p/G0380