Complex glycolipids: key mediators of cell recognition and signaling CAS number: 851608-39-4

N-[(1S,2R,3E)-2-hydroxy-1-[[[O-[N-(2-hydroxyacetyl)-α-neuraminosyl]-(2→3)-O-β-D-galactopyranos yl-(1→4)-β-D-glucopyranosyl]oxy]methyl]-3-heptadecen-1-yl]-Octadecanamide is a complex glycolipid compound with precise structure and specific function. As an important component of cell membranes, these molecules play an irreplaceable core role in life processes such as intercellular communication, immune response, and pathogen recognition.

Chemical Information

Chemical name: N-[(1S,2R,3E)-2-hydroxy-1-[[[O-[N-(2-hydroxyacetyl)-α-neuraminosyl]-(2→3)-O-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl]oxy]methyl]-3-heptadecen-1-yl]-Octadecanamide)

Chemical formula: C59H108N2O22

Molecular weight: 1197.49 g/mol

CAS number: 851608-39-4

Category: Glycolipids

Structural features

The structure of this molecule integrates hydrophilic oligosaccharide chains and hydrophobic lipid tails, forming a typical amphipathic molecular architecture. Its exquisite design is reflected in multiple levels:

l Complex sugar chain structure: The sugar chain part is composed of neuraminic acid (with N-hydroxyacetyl modification), galactose and glucose connected by specific (2→3) and (1→4) glycosidic bonds. This trisaccharide structure containing sialic acid (neuraminic acid derivative) is a common feature of many important biological recognition epitopes (such as blood group antigens, pathogen receptors).

l Special lipid anchoring part: The lipid part contains an unsaturated heptadecene chain and an octadecylamide chain, connected to the sugar chain through an amide bond. This long-chain alkyl structure ensures that the molecule can be stably embedded in the cell membrane lipid bilayer, while its specific stereochemistry (1S, 2R, 3E) is critical for biological activity.

l Integration of multifunctional groups: There are hydroxyl groups, amide bonds, unsaturated olefinic bonds, and carboxyl groups of sialic acid in the molecule at the same time, which provides a structural basis for its participation in various intermolecular interactions (such as hydrogen bonds, electrostatic interactions, and hydrophobic interactions), allowing it to specifically bind proteins (such as lectins, antibodies).

Main applications and potential

Key tools for immunology and infectious disease research

These sialic acid-containing glycolipids are specific cell surface receptors for many viruses, bacterial toxins, and lectins. For example, influenza viruses, parainfluenza viruses, etc. initiate infection by recognizing sialylated glycolipids or glycoproteins on the cell membrane. Providing this compound with a clear structure and high purity is of great value for in-depth study of the host cell invasion mechanism of pathogens and the development of new antiviral inhibitors or vaccine adjuvants.

Potential resources for tumor immunity and marker exploration

The composition and structure of glycolipids on the surface of tumor cells often undergo specific changes, and these changes are closely related to tumor immune escape and metastasis. The complex glycolipid structure represented by this compound can be used as a reference molecule to study tumor-associated carbohydrate antigens and to develop diagnostic methods or new immunotherapy strategies based on glycolipid markers.

Bioactive molecules in neuroscience

Glycolipids, especially glycosphingolipids containing complex sugar chains, play a significant role in nervous system development, myelination and maintenance of neuronal function. The neuraminic acid group in this molecular structure may be involved in nerve cell adhesion and signal transduction, providing a material basis for research in the field of neurodegenerative diseases or nerve regeneration.

Precision building blocks for synthetic biology and materials science

As a natural product analog with a highly defined structure, this compound can be used to construct biomimetic membrane systems, develop biosensors or drug delivery vehicles based on molecular recognition. Its precise sugar sequence and lipid chain provide an ideal template for designing synthetic molecules with specific targeting functions.

Conclusion

N-[(1S,2R,3E)-2-hydroxy-1-...]-Octadecanamide represents a class of complex glycolipid molecules that are extremely valuable at the forefront of life sciences. Its precise chemical structure is directly related to a wide range of vital biological functions. From decoding the codes of cell-to-cell dialogue, to revealing the mechanisms of disease development, to providing inspiration for new treatment strategies, in-depth research on this molecule will continue to promote the advancement of immunology, cell biology, and translational medicine.

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