Disialyl-N-tetrasaccharide—the intelligent messenger that decodes the sugar language of life CAS: 61278-38-4

In the broad landscape of glycobiology, there is a type of molecule that is quietly becoming the new focus of cutting-edge biomedical research and development with its exquisite structure and multiple biological functions. Disialyllacto-N-tetraose (DS-LNT) is one of the outstanding representatives. It is not only a key functional component in human milk oligosaccharides (HMOs), but also an important glycosylation-modified terminal structure on cell surface glycosphingolipids and glycoproteins. It is known as the "precise glycocode" for intercellular communication and a "new target" for disease diagnosis and treatment.

Chemical Information

Chemical name: Disialylacto-N-tetrasaccharide

Common name: Disialyllacto-N-tetraose, DS-LNT

Chemical formula: C₄₈H₇₉N₃O₃₇

Molecular weight: 1290.14 g/mol

CAS number: 61278-38-4

Structural features: unique spatial conformation and functional groups

The structure of disialylacto-N-tetrasaccharide is far from a simple superposition of sugar chains. Its subtlety lies in:

Core skeleton: Lacto-N-tetraose (LNT) is the basic skeleton. The skeleton is composed of galactose (β1-3) N-acetylglucosamine (β1-3) galactose (β1-4) glucose, which is connected in sequence. It is the core structural unit of type I human milk oligosaccharides and many sugar complexes, and has an important basis for biological recognition.

Key modifications: Two sialic acid molecules (usually N-acetylneuraminic acid, Neu5Ac) are connected to the galactose residues at the end of the core skeleton through α2-3 and α2-6 glycosidic bonds respectively. This specific disialylation modification is the core that determines its function.

Three-dimensional space code: Sialic acid is negatively charged, and its introduction significantly changes the hydrophilicity, charge distribution and spatial conformation of the entire oligosaccharide molecule. The specific spatial arrangement formed by disialic acid can be highly specifically recognized by a variety of lectins, receptors and antibodies. It is like a complex "sugar language" that accurately regulates cell adhesion, signal transduction and immune response.

Main applications and advantages

1. Key reference materials for infant nutrition and developmental biology research

Simulates the golden function of human milk: DS-LNT is an important active component in the high-end human milk oligosaccharide mixture. Studies have shown that sialylated HMOs, especially DS-LNT, play a crucial role in cognitive development of infants and young children, directional regulation of intestinal flora (promoting the growth of beneficial bacteria such as Bifidobacterium), and resistance to pathogens (serving as decoy receptors to block virus and bacterial adsorption). DS-LNT is the basic standard and key raw material for developing the next generation of infant formula and evaluating the biological functions of HMOs.

Intestinal health and immune regulation: As a mimic of the sugar structure on the surface of intestinal epithelial cells, DS-LNT can participate in regulating intestinal immune balance and reduce inflammatory reactions. It is an ideal tool molecule for studying the "gut-brain axis", nutritional immunology and other cutting-edge fields.

2. Research on the mechanisms of infectious diseases and new targets for the development of anti-infective drugs

Pathogen recognition “switch”: The virulence factors of many viruses (such as influenza virus, rotavirus) and bacteria (such as Helicobacter pylori, Campylobacter jejuni) initiate infection by recognizing sialylated sugar chains (such as DS-LNT structure) on the cell surface. High purity DS-LNT can be used for:

Mechanistic studies: Elucidate the molecular details of pathogen-host interactions.

Competitive inhibitors: As free "bait" molecules, they block the binding of pathogens to host cells and provide lead compounds for the development of new anti-adhesion therapies.

Vaccine design: As a hapten or carrier, used to prepare antibacterial/antiviral vaccines targeting specific sugar chain structures.

3. Potential stars in the field of cancer diagnosis and immunotherapy

Tumor-associated carbohydrate antigen (TACA): In many malignant tumors (such as colon cancer, breast cancer, melanoma), cell surface glycosylation patterns are abnormal, in which overexpression of sialic acid or specific linkage (such as increased α2-6 linkage) are important features. DS-LNT and similar structures often appear on tumor-associated glycosphingolipids (such as GD1a, GT1b and other gangliosides).

Biomarker development: Antibodies or lectins targeting the structural characteristics of DS-LNT can be used to develop highly specific cancer diagnostic reagents and prognosis monitoring tools.

New strategies for immunotherapy: Sialylated sugar chains represented by DS-LNT can be used as target antigens for cancer vaccines to stimulate the body to produce specific immune responses. At the same time, they are also key molecules that regulate immune cells in the tumor microenvironment (such as inhibiting immune responses through the sialic acid-Siglec pathway). The development of blockers for them is a popular direction in today's tumor immunotherapy.

4. Precision probes for neuroscience research

Abundant expression in the nervous system: Gangliosides containing disialyl structures are abundant in the brain and nervous tissue and are essential for neural development, synaptic plasticity and neural repair. DS-LNT, as its core sugar chain structural unit, is an important molecular tool for studying neurodegenerative diseases (such as Alzheimer's disease), nerve damage and repair mechanisms.

5. Advanced materials for glycoscience and drug delivery systems

Targeted delivery ligands: Since DS-LNT can be recognized by specific receptors (such as certain selectins or Siglec family members), coupling it to the surface of nanomedicines, liposomes or gene carriers can achieve active targeted delivery of drugs to specific cells or tissues (such as inflammatory sites, tumor tissues), improve efficacy and reduce side effects.

Preparation of glycochips: High-purity DS-LNT is a high-quality raw material for the preparation of functional glycochips, which can be used for large-scale screening of proteins that interact with sialylated sugar chains (such as antibodies, lectins, viral proteins), and accelerated drug discovery and biomarker identification.

Conclusion

Disialylacto-N-tetrasaccharide is much more than a complex sugar molecule. It is the "sugar code" for precise regulation of life systems and a "multifunctional bridge" connecting nutrition, immunity, development and disease. From empowering the next generation of high-end infant nutrition to uncovering the pathogenesis of infection and cancer; from developing new immunotherapy pathways based on sugar structures to building intelligent targeted drug delivery systems, DS-LNT has demonstrated irreplaceable value.

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