Lactose-N-new disfucosylhexaose I—a tool sugar for glycobiological research CAS: 62469-99-2

In the cutting-edge field where glycoscience and biomedicine intersect, complex oligosaccharides, as key information carriers in life processes, are increasingly becoming the focus of drug development, disease diagnosis and basic research. Lacto-N-neo-difucohexaose I (Lacto-N-neo-difucohexaoseI) is such a star-level complex oligosaccharide compound with a clear structure and specific functions. It is not only an important structural unit in human milk oligosaccharides (HMOs) and certain glycolipids and glycoproteins, but also a valuable molecular probe for exploring intercellular communication, host-pathogen interactions, and immune regulatory mechanisms.

Chemical Information

Chemical name: Lactose-N-neofucylhexaose I

English name: Lacto-N-neo-difucohexaose I

Chemical formula: C₃₈H₆₅NO₂₉

Molecular weight: 999.91 g/mol

CAS number: 62469-99-2

Structural features

Lactose-N-neofucylhexaose I belongs to the fucosylated lacto-N-neofucylhexaose series oligosaccharides. It has an exquisite structure and distinctive features:

Core skeleton: The hexasaccharide core skeleton is composed of an extended lactosamine (Galβ1-4GlcNAc) unit, which represents an important type of type I (Galβ1-3GlcNAc) and type II (Galβ1-4GlcNAc) lactosamine structures.

Key fucose modifications: Two α-linked fucose (Fuc) groups are attached to its specific galactose (Gal) and N-acetylglucosamine (GlcNAc) residues. This precise fucosylation pattern, especially the key to the formation of Lewis epitopes (such as Lewis a, Lewis b, Lewis x or Lewis y and their analogs), is the structural basis of its biological activity.

Spatial information encoding: Sugar chain branches, linkage types (α1-2, α1-3, α1-4) and fucose substitution positions together form a unique three-dimensional topology that enables it to be recognized with high specificity by specific lectins (such as selectins), antibodies or bacterial adhesins.

Main applications and advantages

1. Key ligands in glycobiology and immunology research

Host-pathogen interaction research: Many pathogens (such as Helicobacter pylori, norovirus, rotavirus, etc.) adhere and invade by recognizing fucosylated oligosaccharides (such as Lewis antigen) on the surface of host cells. Lactose-N-neofucylhexaose I can be used as a standard or competitive inhibitor to study the molecular details of these interactions, providing a starting point for the development of anti-infective therapies such as adhesion inhibitors.

Research on immune cell regulation: The selectin family (such as E-selectin, P-selectin) plays a central role in inflammation and immune cell homing, and its ligands often contain fucosylated structures (such as sLex). Lactose-N-neofucylhexaose I is an ideal tool molecule for studying the binding affinity, specificity and signal transduction of selectins and ligands, helping to understand the mechanisms of inflammatory diseases and cancer metastasis.

Antigenic epitopes for antibody and vaccine development: As defined Lewis antigen-related structures, they can be used to screen or evaluate monoclonal antibodies against specific sugar antigens, or as building blocks for synthetic sugar vaccines designed to induce immune responses against cancer cells or specific pathogens that overexpress these sugar structures.

2. Diagnostic marker research and detection development

Cancer biomarkers: Many tumors (such as gastric cancer, colorectal cancer, pancreatic cancer) are accompanied by abnormal expression of cell surface Lewis antigens (such as CA19-9 related sLea). Lactose-N-neofucylhexaose I can be used as a standard reference material to establish and calibrate glycomic analysis methods based on mass spectrometry, chromatography or chip technology, accurately monitor changes in sugar chain markers in body fluids, and facilitate early diagnosis and prognosis assessment.

Development of microbial detection tools: Utilizing its specific binding to bacterial lectins, this product or its terminal structure can be fixed on the sensor surface to develop a highly specific pathogenic bacteria detection platform.

3. Valuable building blocks of synthetic glycoscience and medicinal chemistry

Receptors or substrates for the chemoenzymatic synthesis of complex sugar chains: Lactose-N-neofucylhexaose I itself can be used as a high-quality acceptor for further glycosylation extension, and can be used to synthesize more complex humanized oligosaccharides or glycoconjugates.

Design of glycomimetics and drug lead compounds: Its precise structural information provides a perfect template for the design and synthesis of small molecules or glycomimetic compounds. These mimetics are expected to become new anti-inflammatory, anti-metastatic or anti-infective drugs.

Conclusion

Lactose-N-neofucylhexaose I is far more than a chemical entity. It is a key word in interpreting the "sugar language" of life and a bridge molecule connecting basic discovery and clinical application. From revealing the molecular mechanisms of infection and cancer to developing new diagnostic reagents and therapeutic strategies, its value runs through multiple dimensions of modern biomedicine.

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