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.
Ac4ManNAz（1,3,4,6-四-O-乙酰基-N-叠氮乙酰基氨基甘露糖）是一种含叠氮基的代谢糖蛋白标记试剂，可以选择性修饰蛋白质，用于细胞标记、跟踪和蛋白质组学分析[1, 2]。Ac4ManNAz是一种点击化学试剂，它含有叠氮基团，可以与含有炔基的分子发生Cu(I)催化的叠氮化物-炔环加成反应（CuAAC）[3]。Ac4ManNAz还可以和含有 DBCO 或 BCN 基团的分子发生环张力驱动的炔-叠氮环加成反应（SPAAC）[4]。
点击化学是一种多功能反应，可用于合成各种缀合物。事实上，任何生物分子都可以使用点击化学方法轻松地用小分子标记，例如荧光染料、生物素等。
点击化学反应发生在两种组分之间：叠氮化物和炔烃（末端乙炔）。叠氮基和炔基在天然生物分子中几乎从未遇到过。因此，该反应具有高度生物正交性和特异性