CAS: 98924-81-3—A key building block in glycochemistry and bioconjugation

2-[(azidoacetyl)amino]-2-deoxy-D-glucopyranose 1,3,4,6-tetraacetate is a carbohydrate derivative with important synthetic value. Its molecule simultaneously integrates an azide group and a fully acetylated sugar ring structure, making it a key intermediate with high flexibility and high reactivity in glycobiological research, synthesis of oligosaccharides and glycoconjugates, and chemical biology applications.

Chemical Information

Chemical name: 2-[(azidoacetyl)amino]-2-deoxy-D-glucopyranose 1,3,4,6-tetraacetate

English name: 2-[(Azidoacetyl)amino]-2-deoxy-D-glucopyranose1,3,4,6-tetraacetate

Chemical formula: C16H22N4O10

Molecular weight: 430.37 g/mol

CAS number: 98924-81-3

Category: Metabolic Probe Reagents

Structural features

The structural design of this compound integrates multiple key functional modules, giving it unique chemical properties:

Azidoacetyl-modified amino group: At the 2-position of the sugar ring, the natural amino group is modified by an azidoacetyl group (-NHCOCH2N3). This design introduces a highly specific azide group (-N3). The azide group is a classic reaction functional group in click chemistry, especially the copper-catalyzed azide-alkyne cycloaddition reaction. It can efficiently and highly selectively connect to alkynes, providing a powerful chemical handle for further functionalization of sugar molecules.

Full acetylation protection: The 1, 3, 4 and 6 hydroxyl groups of the sugar ring are all protected by acetyl groups. This fully protected state ensures that the sugar molecules maintain chemical stability during subsequent multi-step synthesis or storage and prevents unnecessary side reactions. Acetyl group is one of the most commonly used protecting groups in sugar chemistry because it is easy to be selectively removed under mild alkaline conditions, thus paving the way for the subsequent targeted introduction of other sugar units or functional groups.

Flexible synthetic building blocks: This structural combination allows it to be used as an acceptor to participate in the formation of glycosidic bonds through its free 1-position activation to construct more complex oligosaccharide chains; it can also be used as a donor to efficiently conjugate with other biomolecules (such as proteins, lipids, nucleic acids or small molecule probes) through its azide group to prepare glycoconjugates for research.

Main applications and advantages

Glycoconjugates and glycoprotein synthesis

The presence of the azide group makes it a central component in bioorthogonal chemistry strategies. Through click chemical reactions, this compound can be conveniently connected to proteins, peptides or solid-phase carriers carrying alkynyl groups, and used to synthesize homogeneous glycoproteins or glycopeptides with well-defined structures. This is crucial in studying the impact of glycosylation on protein structure, function, stability and recognition processes, and provides a standardized tool for glycoprotein drug development and disease mechanism research.

Complex oligosaccharides and sugar library construction

As a protected glycosyl donor or acceptor, it is an important building block in automated or modular oligosaccharide synthesis. Chemists can take advantage of its selective deprotection or activation properties and orderly connect it with other sugar units to efficiently construct complex oligosaccharide structures, sugar chain libraries or sugar chips containing specific amino sugar modifications, which can be used in drug screening, pathogen identification research and immunology research.

Chemical Biology and Probe Development

The azide group can serve as an introduction site for biolabels or reporter groups. By linking fluorescent dyes, biotin or affinity tags via click chemistry, fluorescent sugar probes, pull-down probes, etc. can be prepared. These probes can be used to track intracellular sugar metabolism in real time, locate sugar-binding proteins, or enrich and identify sugar-interacting molecules from complex biological samples, which has greatly promoted the research progress of glycobiology at the in vivo level.

Application potential in medicinal chemistry and materials science

The sugar derivatives synthesized based on this intermediate show potential in the development of new sugar vaccines, targeted drug delivery systems and biocompatible materials. The introduced sugar structure can adjust the hydrophilicity, recognition specificity and pharmacokinetic properties of the molecule.

Conclusion

2-[(azidoacetyl)amino]-2-deoxy-D-glucopyranose 1,3,4,6-tetraacetate plays a bridging role in the broad field of glycoscience from basic synthesis to cutting-edge biological applications with its exquisite azide functionalization and fully protected design. It is not only a reliable building block for chemists to construct complex sugar structures, but also an important tool molecule that connects chemistry and biology and reveals the secrets of sugar life. Its value continues to be demonstrated in the rising wave of sugar science and sugar drug research and development.

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