CAS: 1971934-97-0—Key chemical probe for glycobiology and metabolic labeling

2-[(2-Azidoacetyl) amino]-2-deoxy-D-mannopyranose is a carbohydrate derivative with a precisely defined structure and belongs to the category of MetabolicProbe Reagents. By specifically introducing bioorthogonal azide groups into the mannose structural backbone, it provides a powerful chemical tool for studying the glycosylation process, cellular metabolic pathways, and the synthesis and function of glycoproteins.

Chemical Information

Chemical name: 2-[(2-azidoacetyl)amino]-2-deoxy-D-mannopyranose

Chemical formula: C8H14N4O6

Molecular weight: 262.22 g/mol

CAS number: 1971934-97-0

Category: Metabolic Probe Reagents

Structural features

The design of this molecule cleverly combines natural sugar structure with artificially introduced bioorthogonal functional groups:

Modified sugar backbone: The molecule uses D-mannopyranose as the basic backbone, and has key modifications on its No. 2 carbon. The hydroxyl group at position 2 was replaced by an amino group and further derivatized to form a 2-deoxy-2-amino structure, which changed its natural metabolism and recognition properties.

Introduction of an azide reporter group: The key modification is to connect an azide group (-N3) to the amino group of the sugar through an acetyl linker arm. This azide group is small, chemically inert, and stable under physiological conditions, but can be covalently bound to reporter molecules such as fluorescent dyes with alkynyl groups, biotin, or affinity tags through efficient and specific click chemistry reactions (such as copper-catalyzed or strain-promoted alkyne-azide cycloaddition reactions).

Metabolic compatibility: The overall structure is designed to be recognized and utilized by intracellular sugar metabolism enzymes, thereby integrating into newly synthesized glycoconjugates (such as glycoproteins, glycolipids) to achieve labeling and tracking of specific glycosylation pathways.

Main applications and advantages

Cell surface glycan labeling and imaging

As a metabolic sugar probe, this molecule can be taken up by cells and enter the biosynthetic pathway of glycans such as sialic acid. Ultimately, azide-tagged glycans are expressed on cell surface glycoproteins or glycolipids. Subsequent linking of fluorescent probes via click chemistry enables visual imaging of specific glycans on the surface of living or fixed cells for studying cell differentiation, activation, cell-cell interactions, and expression of tumor-associated glycoantigens.

Identification and enrichment of glycoproteomics

Metabolic labeling introduces azide groups into the glycoproteome of an entire cell or organism. Click chemistry is then used to link the azide-tagged glycoprotein to a solid support (such as magnetic beads with alkyne groups) or a purification tag (such as biotin), which can specifically enrich glycoproteins from complex protein mixtures. Combined with mass spectrometry analysis, this strategy greatly facilitates the large-scale identification, quantification, and glycosylation site analysis of glycoproteins.

Dynamic study of glucose metabolism pathways

This probe allows the study of dynamic processes of glycosylation on a time-resolved scale. By controlling the time window when the probe is added to cells, newly synthesized glycoconjugates within a certain period of time can be specifically labeled and tracked, thereby analyzing the changes in glycosylation during development, signal transduction or disease progression, and assessing the activity of metabolic pathways.

Drug target discovery and drug delivery applications

Based on its labeling capabilities, it can be used to screen and identify molecules that target specific sugar structures (such as lectins, antibodies, viral receptors). In addition, labeled cell surface azide groups can serve as universal anchoring points to couple functional molecules (e.g., drugs, nucleic acids, nanoparticles) via click chemistry, providing a flexible platform for targeted delivery and cell engineering.

Conclusion

2-[(2-Azidoacetyl) amino] -2-deoxy-D-mannopyranose represents a prime example of the development of chemical biology tools that combines sophisticated synthetic chemistry with cutting-edge bioorthogonal chemistry and metabolic engineering principles. As an efficient metabolic probe reagent, it continues to promote in-depth exploration in the fields of glycobiology, immunology, developmental biology, and disease mechanisms. It is an indispensable molecular key for analyzing the functions of sugar codes in life processes.

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