Lacto-N-difucohexaose II (LNDFH II) in Glycobiology Research (CAS 62258-12-2)

Lacto-N-difucohexaose II (Lacto-N-difucohexaose II) is one of the core functional oligosaccharides that has attracted much attention in the field of glycobiology. It belongs to the human milk oligosaccharide (HMOs) and blood group antigen-related carbohydrate families. It is not only a crucial structural unit in cell surface glycosphingolipids and glycoproteins, but also a "bioinformation molecule" that mediates intercellular recognition, signal transduction and immune regulation. It is becoming an indispensable high-value tool and potential therapeutic agent in cutting-edge biomedical research on infection and immunity, tumor microenvironment, intestinal flora regulation, and targeted drug delivery.

Chemical Information

Chemical name: Lacto-N-difucohexaose II (based on carbohydrate nomenclature)

Common name/abbreviation: LNDFH-II, LNDFH II

Chemical formula: C₃₈H₆₅NO₂₉

Molecular weight: 999.91 g/mol

CAS number: 62258-12-2

Structural features

Lacto-N-difucohexaose II is a hexasaccharide molecule with an exquisite structure. Its unique features are:

Core skeleton and modification: Its molecule takes lactose (Galβ1-4Glc) as the core and connects N-acetyl lactose (Galβ1-3GlcNAc) units through β1-3 bonds to form a typical type I lactose series structure (Lacto-N-series). On this skeleton, there are two fucose (Fuc) residues connected at specific positions. These two fucosylation modifications are the key to its biological activity.

Fucosylation mode: Two α-linked fucoses are located on different sugar units. This specific difucosylation mode enables it to accurately simulate the sugar chain structure of a variety of natural biological ligands, especially closely related to the Lewis series of blood group antigens (such as Lewis a, Lewis b) and secreted antigens.

Structure-activity relationship: The precise glycosidic bond connection (α1-2, α1-3, α1-4) and branched structure determine its high specificity in being recognized by specific lectins (such as selectins, galectins), bacterial adhesins or antibodies. It is an ideal model molecule for studying sugar-protein interactions.

Main applications and advantages

1. Molecular probes for studying infection and immune mechanisms

Pathogen recognition research: Many bacteria (such as Helicobacter pylori), viruses and parasites specifically recognize fucosylated oligosaccharides (such as Lewis antigen) on the host cell surface through adhesion proteins on their surfaces to initiate infection. LNDFH-II can be used as a key standard or competitive inhibitor to elucidate the adhesion mechanism of pathogens and develop new anti-infection strategies.

Immunomodulatory function: As complex oligosaccharides naturally present in human milk, these molecules have a regulatory effect on the development of the infant's immune system and the establishment of intestinal immune homeostasis. LNDFH-II can be used to study how it affects the function of immune cells such as dendritic cells and macrophages, and explore its anti-inflammatory or immune tolerance induction potential.

2. Tumor biology and diagnostic marker development

Research on tumor-associated carbohydrate antigens (TACAs): In various adenocarcinomas (such as gastric cancer, colorectal cancer, and pancreatic cancer), the expression of Lewis antigen on the cell surface often increases abnormally or changes in glycoforms. As a structural analog of Lewis b and other related antigens, LNDFH-II is an important tool for studying abnormal tumor glycosylation, tumor metastasis (involved in selectin-mediated cell rolling) and immune evasion.

Diagnostic reagent development: Using its precise sugar chain structure, highly specific monoclonal antibodies can be developed or a lectin-based detection platform can be constructed for the detection of abnormal sugar chains in serum or tissue samples to facilitate early diagnosis and prognosis assessment of cancer.

3. Intervention targets for intestinal health and microecological regulation

Prebiotics and antibacterial effects: Human milk oligosaccharides (HMOs) protect infant health by selectively promoting the growth of specific probiotics (such as Bifidobacteria) and blocking the binding of pathogens to the intestinal epithelium. As a member of HMOs with a clear structure, LNDFH-II is an ideal choice for studying its prebiotic effects, protecting intestinal barrier integrity and inhibiting pathogen colonization, providing a theoretical basis for the development of the next generation of functional foods or microbial preparations.

4. Drug delivery and therapeutic development

Targeted delivery carrier: Taking advantage of the high expression characteristics of certain lectins (such as selectins) on inflammatory sites or tumor vascular endothelium, LNDFH-II or its derivatives can be modified on the surface of liposomes or nanoparticles to achieve targeted delivery of drugs or genes, improve efficacy and reduce side effects.

Therapeutic antibodies and vaccine design: In tumor immunotherapy, antibodies against tumor-specific carbohydrate antigens (such as anti-Lewis Y) have entered clinical research. LNDFH-II can be used as an antigen for antibody screening, identification and vaccine design. In addition, its immunomodulatory properties also make it a potential therapeutic molecule candidate for autoimmune or allergic diseases.

5. Basic glycoscience and biological tool development

Glycochip core unit: In functional glycomics research, LNDFH-II is one of the key units in constructing high-density glycochips. It is used for high-throughput screening of proteins (lectins, antibodies, enzymes, etc.) that bind to specific sugar structures and to draw sugar-protein interaction networks.

Enzyme tools and standards: As specific substrates or standards for a variety of glycosyltransferases (such as fucosyltransferase) and glycoside hydrolases, it is used for enzyme activity determination, inhibitor screening and enzyme reaction mechanism research to promote the development of glycoengineering.

Conclusion

From being a "guardian" in the early stages of life to becoming a "signpost" in the field of tumors and infections, from a precision probe for basic research to a potential target for translational medicine, Lacto-N-difucohexaose II carries biological information far beyond the molecule itself. It is not only a simple series connection of six monosaccharides, but also a key code to decipher the "sugar language" between cells and connect the microscopic sugar structure and the macroscopic life phenotype.

The above information is provided by the editor of KASONS and is for scientific research only.