Lacto-N-trioseⅡ

Lacto-N-triose II (LNT II) is a neutral human milk oligosaccharide (HMO) classified as a trisaccharide composed of three monosaccharide units linked in a specific sequence: N-acetylglucosamine (GlcNAc), galactose (Gal), and glucose (Glc).

• Abbreviation: LNT II
• IUPAC Name (extended): β-D-GlcpNAc-(1→3)-β-D-Galp-(1→4)-D-Glc
• IUPAC Name (condensed): GlcNAc-(β1-3)-Gal-(β1-4)-Glc
• Molecular Formula: C20H35NO16
• Molecular Mass: 545.49 g/mol
• CAS Number: 75645-27-1

Chemical and Structural Description

• Structure: LNT II consists of a lactose core (galactose β1-4 glucose) with an N-acetylglucosamine residue attached to galactose via a β1-3 glycosidic bond. It is a reducing trisaccharide and serves as a foundational building block for more complex human milk oligosaccharides.
• Physical Properties: It appears as a white to off-white powder, soluble in water, and generally stable under controlled storage conditions. It can be characterized by spectroscopic methods including NMR.
• Production: LNT II is naturally found in human breast milk and can be produced on an industrial scale via enzymatic synthesis or microbial fermentation with engineered biosynthetic pathways for high yield and purity.

Biological and Functional Context

• Occurrence: LNT II is a core structural unit in various oligosaccharides found in human milk, playing a fundamental role in infant nutrition.
• Function: Acts as a prebiotic to selectively promote beneficial gut bacteria such as Bifidobacterium species, supports immune system development, and contributes to protecting the infant gut by anti-adhesive effects against pathogens.
• Industrial Production: Advanced biotechnological processes involving glycosynthase enzymes have enabled continuous, high-yield production of LNT II, making it a valuable ingredient for infant formula and functional foods.

Analytical Confirmation

• Structural and purity analyses rely on methods such as nuclear magnetic resonance (NMR) spectroscopy, high-performance liquid chromatography (HPLC), and mass spectrometry to ensure equivalence with natural LNT II.

Specification Table

Related Compounds

• Lacto-N-tetraose (LNT): A tetrasaccharide with an additional galactose-GlcNAc extension.
• Other HMOs: LNT II serves as a core trisaccharide unit in many complex HMOs in human milk.

Lacto-N-triose II is an important trisaccharide component used to replicate natural breast milk benefits in infant nutrition, helping to foster a healthy gut environment and immune development in infants.

This description integrates detailed chemical, biological, and application aspects of Lacto-N-triose II (LNT II), a key human milk oligosaccharide.

1. https://pubchem.ncbi.nlm.nih.gov/compound/53477860
2. https://pmc.ncbi.nlm.nih.gov/articles/PMC7187300/
3. https://pubs.acs.org/doi/10.1021/acs.jafc.4c12052
4. https://www.elicityl-oligotech.com/human-milk-oligosaccharides-hmo/271-lacto-n-triaose-lnt2-90-nmr.html
5. https://www.sciencedirect.com/science/article/abs/pii/S0144861723005325
6. https://www.elicityl-oligotech.com/human-milk-oligosaccharides-hmo-grafted-on-bsa/273-lacto-n-triaose-lnt2-linked-on-bsa.html
7. https://pubs.acs.org/doi/abs/10.1021/acs.jafc.3c03644
8. https://www.tga.gov.au/resources/resource/compositional-guidelines/lacto-n-tetraose-lnt