CAS: 361154-30-5—Key probe to enable glycobiology research and cell surface engineering

1,3,4,6-Tetra-O-acetyl-N-azidoacetylaminomannose is a carefully designed metabolic sugar probe and an important member of metabolic labeling reagents (MetabolicProbe Reagents). By specifically introducing bioorthogonal functional groups, azide groups, into glycoconjugates on the cell surface, this compound provides researchers with a powerful tool for visualizing, isolating, and analyzing dynamic glycosylation processes, thereby opening up new avenues in basic research, drug development, and diagnostics.

Chemical Information

Chemical name: 1,3,4,6-Tetra-O-acetyl-N-azidoacetylmannose

Common name: N-azidoacetylmannosamine tetraacetyl ester

Chemical formula: C₁₆H₂₂N₄O₁₀

Molecular weight: 430.37 g/mol

CAS number: 361154-30-5

Category: Metabolic Probe Reagents

Structural features

The molecular structure of this compound has been optimized and has the following key features:

Azide group modification: The core feature is that the N-acetyl group of mannosamine is replaced by N-azidoacetyl group. This modification introduces a chemically inert but highly reaction-specific azide group (-N₃) into the sugar molecule without significantly interfering with the natural metabolic pathway.

Full acetylation protection: All hydroxyl groups (positions 1, 3, 4, and 6) on the sugar ring are protected by acetyl groups. This design not only enhances the membrane permeability of the compound, allowing it to enter cells efficiently, but is also hydrolyzed by esterases inside the cell, exposing the active hydroxyl groups, which are recognized and utilized by the cell's sugar nucleotide synthase and glycosyltransferase.

Bioorthogonal reaction handle: The introduced azide group can be used as a "chemical handle" to efficiently and specifically covalently connect fluorescent dyes with alkynyl groups, biotin or other functional molecules through copper-catalyzed or strain-promoted azide-alkyne cycloaddition reactions. This reaction rarely interacts with natural biomolecules in complex biological environments.

Main applications and advantages

Labeling and imaging of cell surface glycans

This compound is taken up by cells and metabolized through the sialic acid biosynthetic pathway, ultimately integrating the azide tag into sialylated glycoproteins and glycolipids on the cell surface. Subsequently, using the click chemical reaction of azide and alkynyl labels, highly sensitive and high spatial and temporal resolution fluorescence imaging of specific glycans on the cell surface can be achieved. This technology is widely used to track dynamic changes in cell surface glycocalyx during development, differentiation, immune activation, and tumorigenesis.

Analysis and identification of glycoproteomics

This probe provides a powerful strategy for the specific enrichment and identification of sialylated glycoproteins in proteomic studies. By introducing azide groups into glycoproteins through metabolic labeling, and then using click chemistry to connect them to solid supports (such as agarose beads) or reporter tags, azide-labeled glycoproteins and their glycopeptides can be selectively separated from complex cell lysates or body fluids to facilitate subsequent mass spectrometry analysis, thereby revealing disease-related glycosylation modifications.

Viruses and Vaccine Research

Many viruses utilize host cell sialic acid as receptors. Using this probe to label host cells, the interaction mechanism between viruses and host cell surface glycans can be studied. In addition, in vaccine development, this technology can be used to engineer the surface glycocalyx of cells or virus-like particles to regulate their immunogenicity, targeting or stability, providing new ideas for the design of new vaccines.

In vivo metabolic labeling and targeting

Its good metabolic compatibility allows this compound to be used for in vivo metabolic labeling in model animals (such as zebrafish and mice). Through in vivo click chemical reactions, it is possible to visualize nascent glycans in the entire organism or specific tissues, or to achieve glycosylation-dependent targeted drug delivery, making it possible to study glycobiological functions and develop targeted therapies in vivo.

Conclusion

1,3,4,6-Tetra-O-acetyl-N-azidoacetylaminomannose is an efficient and specific metabolic probe that combines the sophistication of chemical tools with the complexity of biological metabolism. It not only deepens people's understanding of glycosylation, a key life process, but also promotes the development of innovative diagnostic tools and therapeutic strategies based on glycobiology. It is an important bridge between basic discovery and translational application.

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