Ac4ManNAz

Ac4ManNAz (1,3,4,6-tetra-O-acetyl-N-azidoacetylaminomannose) is an azide-containing metabolic glycoprotein labeling reagent that can selectively modify proteins for cell labeling, tracking, and proteomic analysis [1, 2]. Ac4ManNAz is a click chemistry reagent that contains an azide group and can undergo Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) with molecules containing alkyne groups[3]. Ac4ManNAz can also undergo ring strain-driven alkyne-azide cycloaddition (SPAAC) with molecules containing DBCO or BCN groups[4].

Click chemistry is a versatile reaction that can be used for the synthesis of a variety of conjugates. Virtually any biomolecule can be easily labelled with small molecules, such as fluorescent dyes, biotin, etc using click chemistry method.

Click chemistry reaction takes place between two components: azide and alkyne (terminal acetylene). Both azido and alkyne groups are nearly never encountered in natural biomolecules. Hence, the reaction is highly bioorthogonal and specific.

References:
[1] Han S S, Lee D E, Shim H E, et al. Physiological effects of Ac4ManNAz and optimization of metabolic labeling for cell tracking[J]. Theranostics, 2017, 7(5):1164.
[2] Han S S, Shim H E, Park S J, et al. Safety and optimization of metabolic labeling of endothelial progenitor cells for tracking[J]. Scientific reports, 2018, 8(1): 13212.
[3] Singh M S, Chowdhury S, Koley S. Advances of azide-alkyne cycloaddition-click chemistry over the recent decade[J]. Tetrahedron, 2016, 72(35): 5257-5283.
[4] Vidyakina A A, Silonov S A, Govdi A I, et al. Key role of cycloalkyne nature in alkyne-dye reagents for enhanced specificity of intracellular imaging by bioorthogonal bioconjugation[J]. Organic & Biomolecular Chemistry, 2024.