Key glycobiology tools for precise identification and targeted therapy—CAS: 141342-93-0

Today, with the rapid development of glycobiology and immunotherapy, complex oligosaccharides are no longer just energy substances or structural units, but the core code for intercellular communication, pathogen recognition and immune regulation. Trifucosyl(1-2,1-2,1-3)-iso-lacto-N-octaose (CAS number: 141342-93-0), a highly branched fucosylated lacto-N-octaose with precise structure and specific functions. It is not only a key probe for decoding the function of glycoconjugates in life processes, but also a precious raw material and tool molecule for developing the next generation of targeted drugs, vaccine adjuvants and diagnostic reagents.

Chemical Information

Chemical name: O-6-deoxy-α-L-galactopyranosyl-(1-3)-O-[O-6-deoxy-α-L-galactopyranosyl-(1-2)-O-β-D-galactopyranosyl- (1-3)-O-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1-3)-β-D-galactopyranosyl-(1-4)]-O-2-(acetyl Amino)-2-deoxy-β-D-glucopyranosyl-(1-6)-O-[O-6-deoxy-α-L-galactopyranosyl-(1-2)-O-β-D-galactopyranosyl Base-(1-3)-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl-(1-3)]-O-β-D-galactopyranosyl-(1-4)-D-glucose

Common name: Trifucosyl(1-2,1-2,1-3)-iso-lacto-N-octaose

Chemical formula: C₇₂H₁₂₁N₃O₅₃

Molecular weight: 1876.73 g/mol

CAS number: 141342-93-0

Structural features

Trifucosyl(1-2,1-2,1-3)-iso-lacto-N-octaose is a complex derivative of the core skeleton of lacto-N-octaose. The essence of its structure lies in precise branching modification and specific fucose connection:

Highly branched core skeleton: The eight-saccharide core constructed from repeated units of lactosamine (Galβ1-3/4GlcNAc) forms a stable and extensible spatial conformation, providing a structural basis for multiple recognition.

Specific α-linked fucose modification: 6-deoxy-α-L-galactopyranose (i.e. fucose, Fuc) is introduced at the O-2 position of a specific galactose (Gal) residue. This "trifucosylation" pattern (Trifucosylation) - especially the connection between (1-2) and (1-3) - is a key structural feature that constitutes various blood group antigens (such as Lewis antigens, Le^x, Le^y) and selectin ligands.

Key N-acetylglucosamine (GlcNAc): The structure contains multiple 2-(acetylamino)-2-deoxy-β-D-glucose (GlcNAc) units. Its acetylamino group not only enhances the stability of the molecule, but is also a key site for protein (such as lectin) recognition.

Stable glycosidic bond network: The complex (1-2), (1-3), (1-4), (1-6) glycosidic bond connections constitute a three-dimensional "sugar code", whose specificity is determined by the type of each bond, the anomeric configuration (α/β) and the modification site, giving the molecule extremely high biorecognition specificity and affinity.

Main applications and advantages

1. Core ligands for carbohydrate immunology and vaccine development

Pathogen recognition and neutralization research: Many bacteria and viruses (such as influenza virus, Helicobacter pylori) adhere and infect by recognizing fucosylated antigens (such as Lewis antigen) on the surface of host cells. Trifucosyl(1-2,1-2,1-3)-iso-lacto-N-octaose can be used as a high-purity standard or competitive inhibitor to study the interaction mechanism between pathogens and hosts, providing a molecular basis for the development of anti-adhesion therapies and broad-spectrum vaccines.

Vaccine design and adjuvant development: By covalently linking such oligosaccharides with immunomodulatory activity to carrier proteins, glycoconjugate vaccines can be synthesized to induce efficient and specific antibody responses against certain cancer cells or pathogens expressing specific sugar antigens. Its structure can also be used as a candidate molecule for new vaccine adjuvants to regulate the direction of immune response.

2. Probes and lead compounds for targeted therapy of inflammation and cancer

Selectin-ligand interaction study: The trifucosyl structure of Trifucosyl(1-2,1-2,1-3)-iso-lacto-N-octaose simulates the ligands of natural E-selectin and P-selectin (such as sLe^x). During inflammation and cancer metastasis, leukocytes or cancer cells combine with selectins on the vascular endothelium through such sugar structures on their surfaces to achieve rolling and extravasation. It is a top tool molecule for studying this key process and can be used to develop small molecule/oligosaccharide drugs that inhibit inflammatory response or block tumor metastasis.

Tumor marker research and targeted delivery: Cells of various cancers (such as gastric cancer, colon cancer, and pancreatic cancer) express abnormally high levels of Lewis series carbohydrate antigens. It can be used to prepare specific antibodies, develop cancer diagnostic reagents, or as a targeting head group to construct "sugar-drug conjugates" that specifically deliver drugs and imaging agents to tumor cells.

3. Key tools for basic glycobiology and drug discovery

Lectin specificity identification: As a complex oligosaccharide with a clear structure, Trifucosyl(1-2,1-2,1-3)-iso-lacto-N-octaose is an ideal substrate for identification and characterization of the binding specificity of various animal lectins (such as Galectins, Siglecs), plant lectins and microbial lectins. Helps map "sugar-lectin" interactions.

Functional analysis of sugar synthases and glycosidases: It can be used to evaluate the activity and specificity of key glycosylases such as fucosyltransferases (FUTs), or as a substrate to study the cleavage characteristics of glycosidases, which is crucial for the study of glycosylation-related diseases and the development of enzyme inhibitors.

Molecular simulation and drug design: Its precise chemical structure provides a high-quality three-dimensional model for computer-aided drug design (CADD) for virtual screening and optimization of lead compounds that interact with specific sugar-binding proteins.

Conclusion

Trifucosyl(1-2,1-2,1-3)-iso-lacto-N-octaose is not just a complex sugar chain molecule, it is a precise key to decoding cell surface language and intervening in key disease pathways. From the regulation of inflammatory diseases to the blocking of cancer metastasis, from the construction of next-generation sugar vaccines to the development of precise diagnostic tools, its value runs through the core of cutting-edge biomedical research.

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