Lacto-N-tetraose

Lacto-N-tetraose (LNT) is a complex human milk oligosaccharide (HMO) classified as a tetrasaccharide composed of four monosaccharides: galactose, N-acetylglucosamine, galactose, and glucose linked by β-glycosidic bonds in a linear sequence.

• Abbreviation: LNT
• IUPAC Abbreviation: Gal-β1,3-GlcNAc-β1,3-Gal-β1,4-Glc
• Molecular Formula: C26H45NO21
• Molecular Mass: 707.63 g/mol
• CAS Number: 14116-68-8

Chemical and Structural Description

• Structure: Lacto-N-tetraose has a lactose core (galactose-β1,4-glucose) extended by an additional disaccharide, lacto-N-biose (galactose-β1,3-N-acetylglucosamine), linked by β1,3 glycosidic bonds. It is a reducing sugar with an anomeric center at the terminal glucose, existing in equilibrium between alpha and beta anomers.
• Physical Properties: Appears as a white to off-white powder, slightly soluble in water and methanol, with melting point around 205°C and predicted boiling point about 1173.6°C. It is hygroscopic and should be stored between 2-8°C for stability.
• Classification: LNT is a type I chain oligosaccharide, distinguished by the β1,3 linkage at the non-reducing end (compared to type II chains which have β1,4 linkage).

Biological and Functional Context

• Occurrence: Naturally found in human breast milk, LNT is vital for early infant nutrition.
• Functional Role: LNT functions as a prebiotic, promoting growth of beneficial gut bacteria such as Bifidobacterium species, supports immune modulation, and contributes to shaping a healthy infant gut microbiome.
• Related Compounds: LNT is closely related to lacto-N-neotetraose (type II chain isomer) and other HMOs like lacto-N-biose (disaccharide building block).

Analytical Confirmation

• Characterized by NMR, chromatography, and advanced spectroscopic techniques confirming chemical structure, purity, and biological equivalence to natural HMO.

Specification Table

Lacto-N-tetraose is used to replicate the beneficial roles of human milk oligosaccharides in infant formula and dietary supplements, helping to foster a healthy infant gut environment and immune system.

This detailed description integrates the molecular identity, physical characteristics, biological functions, and practical applications of Lacto-N-tetraose (LNT) as an important HMO.

1. https://en.wikipedia.org/wiki/Lacto-N-tetraose
2. https://pubchem.ncbi.nlm.nih.gov/compound/lacto-N-tetraose
3. https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9696192.htm
4. https://pubchem.ncbi.nlm.nih.gov/compound/121853
5. https://www.tga.gov.au/resources/resource/compositional-guidelines/lacto-n-tetraose-lnt
6. https://layerorigin.com/blogs/blog-layer-origin-nutrition/what-is-lacto-n-tetraose-lnt
7. https://hmdb.ca/metabolites/HMDB0006566
8. https://www.sciencedirect.com/science/article/abs/pii/S0144861723005325
9. https://www.frieslandcampinainstitute.com/uploads/sites/19/2024/02/VanderWoude2024-Pre-clinical-safety-assessment-of-biotechnologically-produced-lacto-N-tetraose-LNT.pdf
10. https://www.medchemexpress.com/lacto-n-tetraose.html