Lacto-N-triose Ⅱ

Lacto-N-triose II (LNT II, GlcNAcβ1-3Galβ1-4Glc) constitutes the essential type 2 chain trisaccharide building block for complex human milk oligosaccharides and N-glycans, appearing as a white lyophilized powder critical for LNnT/LNFP III synthesis and Bifidobacterium-selective prebiotic research. This core scaffold accepts α2-3/6 sialylation and α1-3 fucosylation forming sialyl-Lewis X/Le^x determinants while serving as high-specificity substrate for Bifidobacterium bifidum β3GnTase/β4GalTase enabling 3x acetate yield versus glucose; abundant as biosynthetic intermediate in HMO production and natural type 2 chain extension, it demonstrates gastric stability with selective distal colon utilization by B. longum subsp. infantis, upregulates tight junction proteins (claudin-1↑, occludin↑), inhibits ETEC K99 fimbriae adhesion 70%, and supports neurodevelopment through ganglioside mimicry with >600 g/L solubility and indefinite lyophilized stability ideal for precision glycoengineering and infant nutrition research.

Appearance

• White amorphous lyophilized powder; odorless, mildly hygroscopic.​
• Water solubility >600 g/L; clear solutions pH 6-8.​

Source

• Biosynthetic intermediate for LNnT/LNFP III; type 2 N-glycan chains.​
• β3GnT2/β4GalT1 enzymatic cascade on LacNAc acceptors.​

Molecular Weight and Structure

• 545.49 g/mol, formula C₂₀H₃₅NO₁₆ (CAS 75645-27-1).
• GlcNAcβ1-3Galβ1-4Glc linear type 2 trisaccharide scaffold.​

Sugar Specificity

• B. bifidum β3GnTase/β4GalTase (Km 0.3 mM); Leˣ/sLeˣ precursor.​
• DC-SIGN ligand; resists Bacteroides exo-glycosidases.​

Biological Activity

• 3x Bifidobacterium acetate yield; ETEC K99 inhibition 70%.​
• Tight junction upregulation (claudin-1↑, occludin↑).​

Purity and Microbial Contamination

• ≥95% HPLC/NMR; LacNAc <1%, GlcNAc <0.5%.​
• Endotoxins <10 EU/mg; research-grade sterile.​

Identity and Quality Control

• ¹H-NMR β-GlcNAc H1 4.72 ppm; LC-MS [M+Na]⁺ 568.3.​
• HPAEC GlcNAc:Gal:Glc 1:1:1; anomeric purity >98%.​

Shelf Life and Storage

• Indefinite -20°C lyophilized; 48 months 4°C desiccated.​
• N₂ sealed; <60% RH prevents hydrolysis.​

Applications

• LNnT/LNFP III synthesis scaffold; HMO production intermediate.
• Prebiotic research; glycoengineering standards.​

Key Characteristics

• Universal type 2 chain acceptor; gastric-stable scaffold.
• Bifidobacterium-selective distal colon utilization.​

Citation Links

• https://pubchem.ncbi.nlm.nih.gov/compound/53477860​
• https://www.elicityl-oligotech.com/…/271-lacto-n-triaose-lnt2…​
• https://www.medchemexpress.com/lacto-n-triose-ii.html​
• https://www.elicityl-oligotech.com/…/3671-lacto-n-triose…​
• https://glycosmos.org/structure/LNT-II​
• https://www.cd-bioglyco.com/lacto-n-triose-ii​
• https://hmdb.ca/metabolites/HMDB0006570​
• https://pubchem.ncbi.nlm.nih.gov/compound/lacto-N-triose-II​
• https://foodb.ca/compounds/FDB023981​
• https://www.sigmaaldrich.com/…/lacto-n-triose-ii​