6'-Sialyl LacNAc: A precise key to glycobiology research CAS number: 174757-71-2

At the intersection of glycoscience and biomedicine, glycoconjugates, as the "code language" of cell communication, are increasingly becoming key targets for disease diagnosis and targeted therapy. Among them, 6'-Α-sialic acid-N-acetyllactosamine (6-SIALYL-N-ACETYLLACTOSAMINE), as an important type of sialylated glycan structural unit, is not only a core component of cell surface glycosphingolipids and glycoproteins, but also an indispensable signaling molecule in pathogen recognition, immune regulation, tumor metastasis, neural development and other life processes. Today, it has become a high-profile, high-value raw material and tool molecule in basic research on glycobiology and the development of innovative drugs.

Chemical Information

Chemical name: 6'-Α-sialic acid-N-acetyllactosamine

Common name: 6'-Sialyl LacNAc

English name: 6-SIALYL-N-ACETYLLACTOSAMINE

Chemical formula: C₂₅H₄₂N₂O₁₉

Molecular weight: 674.602 g/mol

CAS number: 174757-71-2

Structural features

6'-Α-Sialyl-N-acetyllactosamine is a trisaccharide structure formed by connecting sialic acid (usually N-acetylneuraminic acid, Neu5Ac) to the 6th hydroxyl group of galactose (Gal) of N-acetyllactosamine (LacNAc, Galβ1-4GlcNAc) through an α-2,6 glycosidic bond. Its unique features are:

Key spatial recognition mark: This structure is the specific recognition epitope of many cell surface receptors (such as selectins, Siglec family receptors) and pathogen adhesion proteins (such as influenza virus hemagglutinin). The α-2,6-linked sialic acid gives the entire sugar chain a specific three-dimensional conformation, allowing it to be recognized by specific binding proteins.

Dynamic biological regulatory switch: The degree and pattern of sialylation can dynamically regulate cell adhesion, immune recognition and signal transduction. 6'-sialylation modification is often closely related to cell differentiation, inflammatory response and malignant transformation status.

Excellent stability and derivatability: As a homogeneous compound with a clear structure, this product has high chemical stability and can be used as a standard for analysis and detection. It can also be used as a glycosylation precursor or core structure for further derivatization through chemical or enzymatic methods for the synthesis of more complex glycans, glycoconjugates or biological materials.

Main applications and advantages

1. Core tools for basic research on glycobiology and immunology

Receptor-ligand interaction studies: 6'-α-Sialyl-N-acetyllactosamine is an ideal standard ligand for studying the interaction of sialic acid-binding proteins (such as selectins, Siglec, influenza virus hemagglutinin) and their sugar ligands. It can be used for surface plasmon resonance (SPR), isothermal titration calorimetry (ITC), cell adhesion inhibition experiments, etc. to accurately analyze binding specificity, affinity and kinetic parameters.

Analysis of immune regulatory functions: The sialic acid-Siglec pathway is an important "self" recognition and inhibitory signaling pathway for immune cells. Using 6'-Sialyl LacNAc with a clear structure, the molecular mechanism of this pathway in maintaining immune homeostasis, regulating inflammatory responses, and tumor immune escape can be deeply studied, providing new targets for immunotherapy.

2. Strategic raw materials for the development of new vaccines and antiviral drugs

Antiviral vaccine design: Many viruses (e.g., influenza virus, coronavirus) initiate infection by recognizing sialoglycans on the surface of host cells through hemagglutinin or lectin proteins on their surface. This product can be used as a key antigenic epitope to prepare glycoconjugate vaccines and induce the production of neutralizing antibodies that can block virus attachment.

Development of anti-adhesion inhibitors: Based on the 6'-α-sialic acid-N-acetyl lactosamine structure, small molecules or polyvalent sugar analogs can be designed and synthesized to serve as competitive inhibitors to block the initial adhesion of pathogens and host cells, thereby preventing or treating infectious diseases.

3. Innovative directions in cancer diagnosis and targeted therapy

Tumor biomarker detection: The sialylation patterns (including α-2,6 sialylation) on the surface of various cancer cells will undergo characteristic changes. They can be used as standards or reference materials to develop cancer diagnostic methods based on mass spectrometry, lectin chips or immunoassays to achieve more accurate early screening and classification.

Targeted drug delivery system: Utilizing specific sialic acid-binding proteins (such as E-selectin) overexpressed on the surface of cancer cells, the 6'-Sialyl LacNAc structure can be integrated into the surface of liposomes, nanoparticles or antibody drug conjugates (ADCs) to achieve active targeting and enrichment of drugs to tumor tissues, improve efficacy and reduce systemic toxicity.

4. Standard substrates for enzymatic analysis and glycosynthetic biology

Glycosyltransferase/Glycosidase Characterization Analysis: 6'-A-Sialyl-N-acetyllactosamine is a specific substrate for sialyltransferases (especially the ST6GAL family) and a potential substrate for neuraminidase. It can be used to measure enzyme activity, screen inhibitors, and study enzyme kinetics. It is an important basis for related drug discovery and tool enzyme development.

Chemical-enzymatic synthesis module: As a "building module" with a uniform structure, this product is a key precursor for the one-step extended synthesis of more complex glycan chains (such as sialyl Lewis X) with important biological functions by enzymatic or chemoenzymatic methods, which greatly promotes the development of synthetic glycobiology.

Conclusion

From decoding basic life processes to cutting-edge innovative therapy design, deciphering the sugar code is reshaping the landscape of modern biomedicine. 6'-α-Sialyl-N-acetyllactosamine is not only an indispensable precision research tool in this field, but also a bridge between basic discovery and translational applications. Whether you are exploring the secrets of regulating the immune microenvironment, designing the next generation of anti-infectious vaccines, or developing highly selective tumor targeting strategies, this sugar molecule with a well-defined structure will provide a key breakthrough for your research.

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