5-azido-5-deoxy-sialic acid: a precision probe for glycobiological research 123457-69-2

5-azido-3,5-dideoxy-Neuraminic acid is an artificially designed and modified sialic acid analogue. As an indispensable tool molecule in modern glycobiology and chemical biology research, it is widely used in the frontier fields of life sciences, especially as metabolic probe reagents. Its unique azide group provides researchers with a window to dynamically analyze the complex and critical biological process of cell surface glycosylation.

Chemical Information

Chemical name: 5-azido-3,5-dideoxy-D-glyceryl-β-D-galactose-nonan-2-pyroneic acid (commonly referred to as 5-azido-5-deoxy-sialic acid)

Common name: 5-Azido-Neu5Ac

Chemical formula: C9H15N3O8

Molecular weight: 293.23 g/mol

CAS number: 123457-69-2

Category: Metabolic Probe Reagents

Structural features

This molecule has been precisely engineered and modified based on the structure of natural sialic acid (N-acetylneuraminic acid, Neu5Ac), thus possessing unique chemical and biological properties:

Active azide group: At the C5 position of the sugar ring, the hydroxyl group is replaced by a chemically active azide group (-N3). This modification is the chemical basis for its function as a probe. The azide group can be efficiently and specifically covalently linked to alkyne-containing reporter molecules (such as fluorescent dyes, biotin, or affinity tags) through highly selective "click chemistry" reactions (such as copper-catalyzed Huisgen cycloaddition reaction).

Deoxygenated configuration: The deoxygenated configuration at both C3 and C5 positions, especially the modification at the C5 position, enables it to serve as a substrate or analog for specific enzymes in the sialic acid biosynthetic pathway, thereby being recognized and utilized by the intracellular glycosylation mechanism.

Metabolic compatibility: Although modified, its core skeleton is still highly similar to natural sialic acid, allowing it to be taken up by cells and incorporated into newly synthesized sialoglycans as a precursor to mark cell surface sialylation modifications.

Main applications and advantages

Dynamic labeling and imaging of cell surface glycosylation The core application of

as a metabolic probe is to deliver the molecule to living cells. Cells will use it as a substrate and integrate it into the sugar chain ends of cell surface glycoproteins and glycolipids through the endogenous sialic acid metabolism pathway. Subsequently, the newly synthesized sialic acid modifications on the cell surface can be specifically fluorescently labeled, enriched or purified using the click chemical reaction between the azide group and the alkynyl label. This method makes it possible to visualize and study dynamic changes in cell surface glycosylation in real time and with high sensitivity, and is widely used in research on developmental biology, immune cell recognition, pathogen-host interactions, etc.

Identification and enrichment of glycoproteomics

In functional proteomics research, using its metabolic labeling properties, combined with click chemistry and mass spectrometry technology, it is possible to systematically identify and quantitatively analyze newly synthesized sialic acid-modified glycoproteins under specific periods or conditions. This approach provides temporal resolution that is difficult to achieve with traditional enrichment methods and helps discover key glycosylation events and biomarkers associated with cell state transitions (e.g., activation, differentiation, carcinogenesis).

Research on the infection mechanism of viruses and pathogens

The infection process of many viruses and bacteria relies on binding to sialic acid receptors on the host cell surface. By labeling host cells with this probe, the specific interaction sites of sialic acid modification between pathogens and host cells can be carefully studied, the molecular mechanism of infection can be analyzed, and target information can be provided for the development of new antiviral or antibacterial strategies.

Research on glycosylation biosynthetic pathway

This molecule can be used as a tool to study the activity and function of sialic acid-related biosynthetic enzymes (such as sialyltransferases), or to screen small molecule inhibitors or modulators that affect the glycosylation pathway. It has a fundamental supporting role in understanding congenital glycosylation diseases and related drug development.

Conclusion

With its exquisite "biocompatibility" and "chemical orthogonality" design, 5-azido-5-deoxy-sialic acid perfectly bridges the complex metabolic processes in vivo and efficient in vitro connection chemistry. It converts the originally difficult-to-capture glycosylation dynamics on the cell surface into visible, detectable, and analyzable chemical signals. It is a powerful tool for in-depth exploration of the third chapter of the "code of life" called glycobiology, and continues to promote progress from basic cell biology to translational medical research.

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