3'-(N-Glycolylneuraminolactose)—the core oligosaccharide in glycobiology research 81275-44-7

3'-(N-Glycolyl-a-neuraminosyl)lactose, as an important oligosaccharide molecule, occupies a key position in the field of glycobiology. It is a component of cell surface glycoconjugates and is widely involved in basic biological processes such as cell recognition, signal transduction and immune regulation. As glycoscience becomes increasingly important in disease mechanisms and drug development, this molecule has become a core tool for exploring the mysteries of life and promoting biomedical innovation.

Chemical Information

Chemical name: D-Glucose, O-[N-(2-hydroxyacetyl)-α-neuraminosyl]-(2→3)-O-β-D-galactopyranosyl-(1→4)-

Common name: 3'-(N-Glycolyl-a-neuraminosyl)lactose

Chemical formula: C23H39NO20

Molecular weight: 649.55 g/mol

CAS number: 81275-44-7

Category: Oligosaccharides

Structural features

3'-(N-Glycolyl-a-neuraminosyl)lactose is a trisaccharide derivative. Its structure consists of a lactose core (galactose-β(1→4)-glucose) and modified neuraminic acid residues through specific bonds, showing unique physical and chemical properties:

Specific glycosidic bond connection: The neuraminic acid derivative (N-glycolylneuraminic acid) is connected to the galactose moiety in lactose through an α(2→3) bond. This connection method is common in natural sugar chains and determines the accuracy and selectivity of the interaction between the molecule and the receptor.

Functional modification group: The N-position of neuraminic acid is replaced by a hydroxyacetyl group to form an N-glycolylneuraminic acid structure. This modification enhances the hydrophilicity and structural diversity of the molecule, allowing it to play a special role in the biorecognition process. Compared with unmodified neuraminic acid, it may affect the binding affinity to lectins or antibodies.

Spatial conformational flexibility: The polyhydroxy structure and branch design of the oligosaccharide chain give the molecule a certain conformational flexibility, which helps to adapt to different protein binding pockets, thereby mediating specific intercellular communication or pathogen attachment.

Main applications and advantages

1. Key probes for glycobiology and cell communication research

In basic scientific research, 3'-(N-Glycolyl-a-neuraminosyl)lactose can be used as a model molecule to decipher the functions of glycoconjugates in physiological and pathological processes:

Analysis of cell recognition mechanism: This molecule simulates natural epitopes in cell surface glycolipids or glycoproteins, helping researchers to elucidate the specific role of sugar chains in cell adhesion, pathogen infection (such as virus or bacterial binding), and immune cell trafficking, such as its role in the recognition of influenza virus hemagglutinin or bacterial toxins.

Glycosylation pathway research: As a substrate for enzymatic synthesis or degradation, it can be used to study the activity and specificity of glycosyltransferases or glycoside hydrolases, and promote the construction of sugar metabolism network maps.

2. Potential tools for disease diagnosis and biomarker development

Changes in sugar chain structure are closely related to various disease states, making this molecule showing potential in the field of diagnosis:

Cancer and inflammatory biomarkers: In some tumors or inflammatory diseases, cell surface glycosylation patterns may be abnormal, such as increased expression levels of N-glycolylneuraminic acid, which is associated with the progression of some cancers. This molecule can be used to develop detection reagents or arrays to help monitor disease-specific sugar epitopes and provide new ideas for early diagnosis.

Autoimmune disease research: Since N-glycolylneuraminic acid is less common in humans (mainly found in other mammals), it may trigger an immune response as a foreign antigen. Therefore, it can be used as an antigen mimic for antibody detection or immunomodulation mechanism exploration in autoimmune disease models or xenograft studies.

3. Inspiring molecules for drug development and therapeutic strategies

Based on its biological activity, 3'-(N-Glycolyl-a-neuraminosyl)lactose provides the molecular basis for innovative therapies:

Anti-infective drug design: By competitively inhibiting the sugar binding of pathogens to host cells, this molecule or its derivatives may be developed as antiviral or antibacterial agents, such as blocking the process of viral entry into cells.

Immunomodulator candidate: In immunotherapy, the sugar chain structure can regulate inflammatory response or tolerance. This molecule may be used to design glycomimetic drugs to intervene in excessive immune responses or enhance vaccine potency, especially in glycoengineered vaccine carriers.

Targeted delivery system components: Using the specific recognition ability of oligosaccharides, the molecule can be integrated into nanocarriers or drug conjugates to achieve cell or tissue targeting, improve treatment accuracy and reduce side effects.

Conclusion

3'-(N-Glycolyl-a-neuraminosyl)lactose is not only an oligosaccharide with a complex structure, but also a bridge between basic science and clinical applications. From decoding cell communication codes to promoting precision medicine, its multi-dimensional value in glycobiology, diagnostics and therapeutics is gradually emerging. With the advancement of glycoscience technology, this molecule is expected to have a more profound impact in the understanding of disease mechanisms, the discovery of new biomarkers, and the development of next-generation glycosylation therapies, making a unique contribution to human health.

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