TF-pLNnH I (Thomsen–Friedenreich–para-Lacto-N-neohexaose I)

TF-pLNnH I (Thomsen–Friedenreich–para-Lacto-N-neohexaose I) is an exceptionally rare, multifunctional human milk oligosaccharide (HMO) combining the tumor-associated Thomsen-Friedenreich (TF) antigen (Galβ1-3GalNAcα-Ser/Thr mimic) with a trifucosylated para-lacto-N-neohexaose (pLNnH) backbone, typically structured as Galβ1-3GalNAcα1-[Fucα1-2Galβ1-4(Fucα1-3)GlcNAcβ1-3][Fucα1-2Galβ1-4GlcNAcβ1-6]Galβ1-4Glc, where the TF disaccharide caps one branch while fucose residues create Lewis X/H-type epitopes on the type-2 chain para-structure. Present at ultratrace levels (<0.001% total HMOs) in secretor/Lewis-positive colostrum, this hybrid glycan integrates neonatal prebiotic functions with cancer glycoantigen research utility, biosynthesized by C1GalT1 (T-synthase) plus FUT2/3 fucosyltransferases. The TF moiety confers galectin-3 binding and tumor cell apoptosis induction, while trifucosylation provides extreme pathogen decoy activity against norovirus, Helicobacter pylori, and E. coli F18 via multivalent lectin blockade. Hyper-bifidogenic for B. infantis, it resists pathogenic sialidases/fucosidases while fueling mucin glycosylation and immune tolerance via DC-SIGN. As a synthetic analytical standard (m/z ~1558 [M-H]-), TF-pLNnH I enables isomeric HMO resolution by LC-IM-MS, dual-role probing in oncology (TF-targeted CAR-T) and neonatology (NEC prevention synbiotics), and precision infant formula design matching maternal secretor phenotypes for microbiome/anticancer priming.

Appearance

• White to off-white lyophilized amorphous powder.
• Hygroscopic; nitrogen-flushed for stability.​

Source

• Negligible in mature milk; trace in secretor+ colostrum.
• Regioselective enzymatic galactosylation/fucosylation of pLNnH.​

Molecular Weight and Structure

• Formula: C56H91N4O41F3; MW 1558.57 g/mol.
• TFα-Galβ1-3GalNAc-[triFuc-paraLNnH] branched type-2/hybrid core.​

Sugar Specificity

• TF/galectin-3 + tri-Lex/H selective for tumor lectins/pathogen adhesins.
• B. infantis exclusive; pathogenic GH29-resistant.​

Biological Activity

• Dual-function: Induces cancer cell apoptosis (galectin-TF); >98% norovirus block.
• Hyperbifidogenic: 10x B. infantis selective proliferation.​

Purity and Microbial Contamination

• ≥98% by LC-MS/NMR; loss on drying ≤5%.
• Endotoxin ≤0.01 EU/mg; heavy metals ≤10 ppm.​

Identity and Quality Control

• TIMS-TOF CCS isomer separation, HRMS, 2D-NMR TF confirmation.
• TF-specific peanut lectin binding, fucosidase sequencing.​

Shelf Life and Storage

• 2 years at -80°C lyophilized; stable under recommended conditions.
• Desiccated, single-use aliquots.​

Applications

• Cancer glycoimmunotherapy; HMO isomeric standards.
• Precision synbiotics, TF biomarker assays.​

Key Characteristics

• Unique TF-HMO hybrid; multifunctional antiinfective/anticancer.
• Watersoluble (>100 mg/mL); isobar reference standard.​

Citation Links

• https://pmc.ncbi.nlm.nih.gov/articles/PMC9787824/​
• https://www.nbinno.com/?news%2FAXW-tf-plnh-i-cas120864-60-0​
• https://research-portal.uu.nl/en/publications/characterization-of-rare-trifucosylated-human-milk-oligosaccharid/​
• https://pubs.acs.org/doi/10.1021/acs.analchem.4c06081​
• https://pmc.ncbi.nlm.nih.gov/articles/PMC11370726/​
• https://pmc.ncbi.nlm.nih.gov/articles/PMC12583426/​
• https://glyconnect.expasy.org/hmo/structures​
• https://pmc.ncbi.nlm.nih.gov/articles/PMC9235823/​
• https://www.elicityl-oligotech.com/human-milk-oligosaccharides-hmo​
• https://www.sciencedirect.com/science/article/pii/S0889157525008890