Lactodifucotetraose

Lactodifucotetraose (DFL) is a complex sugar molecule classified as a human milk oligosaccharide (HMO) and is a tetrasaccharide formed by four monosaccharide units: two L-fucoses, one D-galactose, and one D-glucose.

• Abbreviation: DFL
• IUPAC Name: α-L-Fucopyranosyl-(1→2)-β-D-Galactopyranosyl-(1→4)-[α-L-Fucopyranosyl-(1→3)]-D-glucopyranose
• Molecular Formula: C24H42O19
• Molecular Mass: 634.58 g/mol
• CAS Number: 20768-11-0

Chemical and Structural Description

• Structure: Lactodifucotetraose comprises a lactose backbone (D-galactose and D-glucose) with two L-fucose residues. One fucose is attached to galactose via an α-(1→2) glycosidic bond and the second fucose is attached to glucose via an α-(1→3) glycosidic bond.
• Physical Properties: Typically, DFL is a white to off-white powder, highly purified by commercial processes. Minor saccharides (such as D-lactose, L-fucose, D-galactose, and D-glucose) may be present in trace amounts.
• Source: DFL is naturally found in human breast milk and can be produced industrially by microbial fermentation with genetically engineered organisms.

Biological and Functional Context

• Occurrence: It is a natural constituent of human milk oligosaccharides, important for infant nutrition.
• Classification: DFL is one of the more complex HMOs, recognized for its specific prebiotic and immune-modulating functions.
• Functional Role: DFL supports growth of beneficial gut bacteria (such as bifidobacteria), helps in developing the infant immune system, and may provide protection against enteric pathogens through anti-adhesive properties.

Analytical Confirmation

• Structural Analysis: The definitive molecular structure and purity are established by advanced techniques such as nuclear magnetic resonance (NMR) and liquid chromatography.

Specification Table

Related Compounds

• 3-Fucosyllactose (3-FL) and 2′-Fucosyllactose (2′-FL): HMOs with similar molecular backbones and differing fucose positions; DFL is distinguished by presence of two fucose residues.

Lactodifucotetraose is used in infant nutrition and food supplements to mimic natural functions of HMOs in human milk, fostering healthy gut flora and supporting infant immune defense.

1. https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1741610.htm
2. https://en.wikipedia.org/wiki/Lactoferrin
3. https://pubs.acs.org/doi/10.1021/acs.jafc.3c06887
4. https://link.springer.com/article/10.1007/s00018-005-5368-9
5. https://pubchem.ncbi.nlm.nih.gov/compound/126456119
6. https://pubmed.ncbi.nlm.nih.gov/8527233/
7. https://www.sciencedirect.com/science/article/abs/pii/S0924857908003440
8. https://www.cambridge.org/core/services/aop-cambridge-core/content/view/94A9DEF1D8A65060CAEA9FC4D0EC35F8/S0007114500002191a.pdf/occurrence_structure_biochemical_properties_and_technological_characteristics_of_lactoferrin.pdf
9. https://www.ffhdj.com/index.php/FunctionalFoodScience/article/view/1407/4145