Monofucosylated isomeric lactose-N-octasaccharide: biorecognized sugar CAS number: 692776-59-3

In the sophisticated communication network of life sciences, sugar chains, a string of "codes" cleverly connected by simple sugars, are the core language of intercellular dialogue, pathogen recognition and immune response. Among the many complex sugar structures, Monofucosyl (1-3)-iso-lacto-N-octaose stands out. It is not only a complex oligosaccharide molecule, but also a precious blueprint and key raw material for decoding cell-specific recognition and developing the next generation of targeted therapies. As an important derived member of the human milk oligosaccharide family, its precise chemical structure determines its unique biological functions, and it is becoming a frontier focus in the fields of immune regulation, targeted drug delivery, and cancer treatment.

Chemical Information

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

Common name: Monofucosylated isomerized lactose-N-octasaccharide (MF-LNO)

Chemical formula: C₆₀H₁₀₁N₃O₄₅

Molecular weight: 1584.44 g/mol

CAS number: 692776-59-3

Structural features: sophisticated identification module

This molecule is a highly branched complex octasaccharide. The essence of its structure lies in the specific fucose modification of the classic lactose-N-octose core skeleton. Its unique features are:

Precise spatial architecture: The molecule takes specific isomeric lactosamine structural units as the core and is connected through precise β-(1→3) and β-(1→4) glycosidic bonds to form a stable and clear three-dimensional conformation scaffold. This conformation is the basis for specific binding to its receptors, such as selectin family proteins.

Key fucose capping: On a specific N-acetylglucosamine residue, a 6-deoxy-L-galactose (i.e. fucose) is connected via α-(1→3). This monofucosylation modification is the "soul" of molecules that perform advanced biological functions. It constitutes the core recognition motif of classic selectin ligands such as Sialyl Lewis X (sLeˣ).

Diverse information encoding: The alternating galactose, N-acetylglucosamine and terminal glucose in the molecule provide abundant hydrogen bond donor and acceptor sites, and shape a specific charge distribution and hydrophobic surface, allowing it to be recognized by the corresponding lectin or antibody with high affinity and specificity.

Main applications and advantages

1. Core ligands for targeted therapy of inflammation and cancer

Inhibits abnormal cell adhesion: This molecule is a natural high-affinity ligand mimic of cell adhesion molecules such as E-selectin and P-selectin. During inflammation and tumor metastasis, cancer cells or activated leukocytes bind to selectins on vascular endothelial cells through structures such as overexpressed sLeˣ on the surface, initiating rolling adhesion and subsequent migration. Providing high-purity MF-LNO can serve as a competitive inhibitor to block this pathological process and provide lead compounds for the development of anti-inflammatory and anti-tumor metastasis drugs.

Targeted drug delivery carrier: Utilizing the specific binding ability of this oligosaccharide to selectins, it can be coupled to the surface of nanoliposomes, polymer micelles or antibody drug conjugates (ADC) to construct a "smart" targeted delivery system. This system can precisely deliver therapeutic drugs to the site of inflammation or the metastatic tumor microenvironment, significantly improving efficacy and reducing systemic toxicity.

2. Enabling tools for immunotherapy and cell therapy

Regulating immune cell homing: The homing of lymphocytes to specific tissues (such as lymph nodes, inflamed intestines) depends on the interaction between L-selectin on their surface and vascular addressin glycoprotein ligands. MF-LNO and its derivatives can be used to study and regulate this process, and are expected to optimize the in vivo transport and localization of therapeutic cells in adoptive cellular immunotherapy (such as CAR-T) and enhance their tumor infiltration ability.

Glycoengineered adjuvants for vaccine design: Integrating such oligosaccharide structures with clear immunomodulatory functions into vaccine antigens or delivery carriers can directionally regulate the type and intensity of immune responses, providing new strategies for the development of safer and more effective therapeutic vaccines (such as anti-cancer vaccines).

3. The gold standard for basic research and diagnostic development

A key tool for glycobiology research: MF-LNO is an ideal standard and probe for studying the selectin-ligand interaction mechanism and the function of sugar chains in cell signal transduction. Its availability has greatly promoted in-depth research on sugar-binding protein specificity, structure-function relationships, and sugar chain biosynthetic pathways.

Disease biomarkers and detection targets: The levels of sLeˣ and related sugar chain structures in the serum or tissues of patients with various cancers (such as colorectal cancer, pancreatic cancer) are abnormally elevated. Therefore, MF-LNO can be used as an important antigen reference for preparing specific monoclonal antibodies, developing high-sensitivity ELISA detection kits or constructing biosensors to facilitate early screening and prognosis monitoring of cancer.

Conclusion

Monofucosylated isomeric lactose-N-octasaccharide is much more than a lengthy chemical name can summarize. It is a masterpiece of nature's exquisite glycocryptography and serves as a bridge between basic glycoscience and cutting-edge biomedical applications. From suppressing lethal tumor metastasis to guiding precise drug missiles; from decoding the navigation map of the immune system to lighting up the detection window for early diagnosis, its value is being continuously discovered.

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