Neu5Gcα2,3Galβ1,4GlcNAc

Neu5Gcα2,3Galβ1,4GlcNAc is a sialylated trisaccharide motif featuring N-glycolylneuraminic acid (Neu5Gc) in an α2-3 linkage to galactose β1-4 N-acetylglucosamine, recognized as a nonhuman glycan absent in humans due to a CMAH gene mutation but incorporated via dietary sources like red meat. While not a classical human milk oligosaccharide (HMO)—which exclusively contain Neu5Ac—this structure appears in bovine/porcine milks and serves as a xenogeneic antigen in glycomics research. Neu5Gc’s extra hydroxyl group (vs. Neu5Ac) confers unique immunogenicity, triggering anti-Neu5Gc antibodies in humans that form immune complexes linked to chronic inflammation, cancer progression (“xenosialylation”), and xenograft rejection. In HMOs context, it’s studied for comparative sialylation, microbial sialidase specificity, and as a synthetic analog in prebiotic/glycan array applications mimicking type-2 chain sialyl motifs. This glycan binds selectins/Siglecs, influences gut microbiota adhesion, and holds potential in oncology biomarkers, with synthetic versions aiding immunotherapy design against Neu5Gc-enriched tumors.

Appearance

• White lyophilized powder, amorphous or crystalline solid.
• Hygroscopic; often desiccated for stability.​

Source

• Found in ruminant/bovine milk glycans, porcine mucins; dietary origin in humans.
• Chemoenzymatic synthesis using ST3Gal3/4 transferases and CMP-Neu5Gc.

Molecular Weight and Structure

• Formula: C23H38N2O19; MW 634.55 g/mol (reducing end).
• Neu5Gcα2→3Galβ1→4GlcNAcβ (type-2 core with nonhuman sialic acid).​

Sugar Specificity

• α2,3-Neu5Gc selective for anti-Neu5Gc antibodies, Siglec-4.
• Distinguished from Neu5Acα2,3 by C5-hydroxyl; poor HMO microbial utilization.​

Biological Activity

• Induces human IgG/IgM responses, promoting inflammation/cancer metastasis.
• Inhibits selectin-mediated adhesion; potential prebiotic for Neu5Gc-utilizing bacteria.

Purity and Microbial Contamination

• 95% by HPLC/NMR for research grades.
• Endotoxin <0.1 EU/mg; bioburden <10 CFU/g post-sterile filtration.​

Identity and Quality Control

• NMR (1H/13C), HRMS (m/z 633 [M-H]-), linkage-specific exoglycosidase digests.
• Monosaccharide analysis, heavy metals <5 ppm.​

Shelf Life and Storage

• 2-3 years at -20°C lyophilized; solutions stable 2 weeks at 4°C.
• Desiccated, light-protected; minimize freeze-thaws.​

Applications

• Cancer/xenotransplant biomarkers; glycan microarrays for antibody profiling.
• Comparative HMO studies, anti-inflammatory glycoengineering.

Key Characteristics

• Highly immunogenic nonhuman sialyl-type 2 antigen.
• Water-soluble (>50 mg/mL), stable for array/probe use.​

Citation Links

• https://pubchem.ncbi.nlm.nih.gov/compound/91862595​
• https://pmc.ncbi.nlm.nih.gov/articles/PMC6724515/​
• https://pmc.ncbi.nlm.nih.gov/articles/PMC6753469/​
• https://pubchem.ncbi.nlm.nih.gov/compound/156613026​
• https://oro.open.ac.uk/38117/1/c1sc00120e.pdf​
• https://pmc.ncbi.nlm.nih.gov/articles/PMC3406618/​
• https://www.sciencedirect.com/science/article/pii/S2161831322010110​
• https://glyconnect.expasy.org/hmo/structures​
• https://pmc.ncbi.nlm.nih.gov/articles/PMC9237113/​
• https://www.jstage.jst.go.jp/article/tigg/30/172/30_1734.1SE/_article