The Application of Click Chemistry Reactions in Plant Cell Labeling

doi:10.11983/CBB22252

Abstract

Abstract: Click chemistry, also known as "link chemistry" or "speed-matching combinatorial chemistry", is the development of a powerful, highly reliable, and highly specific set of reactions for the rapid synthesis of new compounds through the connection of carbon-heteroatomic bonds (C-X-C). Click chemistry has been progressing greatly in drug development, new material synthesis, material surface functionalization modification and biological macromolecular labeling. Pioneers of click chemistry was awarded the Nobel Prize in Chemistry in 2022. This review briefly introduces the principles, reaction types and applications of click chemistry, summarizes the research progress of click chemistry in labeling biological macromolecules, especially in its application to plant cell wall polysaccharide labeling, and provides new ideas for the study of plant cell wall synthesis, structure and dynamic transport.

Key words: click chemistry reaction, azide-alkyne cycloaddition, cell wall, glycan

Yuge Zhang, Xiaoyan Yuan, Guifang Zhang, Yujian Li, Jinhuan Yin, Jinxing Lin, Xiaojuan Li. The Application of Click Chemistry Reactions in Plant Cell Labeling[J]. Chinese Bulletin of Botany, 2023, 58(6): 956-965.

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URL: https://www.chinbullbotany.com/EN/10.11983/CBB22252

https://www.chinbullbotany.com/EN/Y2023/V58/I6/956

Figures/Tables 3

Figure 1 Two types of cycloadditions reactions CuAAC (A) and SPAAC (B) CuAAC uses end-group alkynes and azides to form 1,4-disubstituted-1,2,3-triazole catalyzed by copper ions; SPAAC uses cyclooctyne and azide reactions to form stable triazoles. CuAAC: Copper (I) catalysed azide-alkyne cycloaddition; SPAAC: Strain-promoted azide-alkyne cycloaddition

Figure 2 The flow diagram of applying click chemistry to labeling cell wall glycan The non-natural sugars in the figure refer to the monosaccharide components in the cell wall, and do not refer to specific sugar molecules. ① Exogenous monosaccharide analogues are metabolized into cells through the remedial glycan synthesis pathway; ② Probes containing fluorophores click with glycans that contain monosaccharide analogues and are deposited on the cell wall; ③ Fluorescence is detected to investigate the arrangement of monosaccharide analogues in plants, as shown in the fluorescent image of pectin RG-II in plant cell wall; ④ Fluorescence microscopy imaging of pectin distribution in plant roots labelled by click chemistry (bar=50 μm).

Table 1 Sugar analogues containing alkyne or azide functional groups in Arabidopsis thaliana

外源糖	毒害作用	组织定位
炔基化岩藻糖	无毒性	分布于根表皮的细胞壁中
8-叠氮-8-脱氧-3-脱氧- D-甘露-2-辛酮糖酸	无毒性	分布于整个初生壁中, 但在质膜附近标记更强
叠氮基N-乙酰氨基葡萄糖	无毒性	根中均有分布, 分生区分布较多
叠氮乙酰基阿拉伯糖	无毒性	根中均有分布
叠氮乙酰基岩藻糖	无毒性	根中均有分布
6-脱氧-炔基葡萄糖	抑制根生长	定位于根毛凸起和突出的根毛尖端

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