点击化学反应在植物细胞标记中的应用

doi:10.11983/CBB22252

植物学报 ›› 2023, Vol. 58 ›› Issue (6): 956-965.DOI: 10.11983/CBB22252

点击化学反应在植物细胞标记中的应用

张御格¹^,², 袁笑妍¹^,², 张贵芳¹^,², 李雨健¹^,², 殷金环¹^,², 林金星¹^,², 李晓娟¹^,²^,^*()

¹北京林业大学生物科学与技术学院, 林木、花卉遗传育种教育部重点实验室, 北京 100083
²林木育种与生态修复国家工程研究中心, 北京 100083

收稿日期:2022-10-25 接受日期:2023-02-28 出版日期:2023-11-01 发布日期:2023-11-27
通讯作者: * E-mail: lixj@bjfu.edu.cn
基金资助:
国家自然科学基金(91954202);国家自然科学基金(31871349);北京林业大学科技创新计划(2019JQ03003)

The Application of Click Chemistry Reactions in Plant Cell Labeling

Yuge Zhang¹^,², Xiaoyan Yuan¹^,², Guifang Zhang¹^,², Yujian Li¹^,², Jinhuan Yin¹^,², Jinxing Lin¹^,², Xiaojuan Li¹^,²^,^*()

¹Key Laboratory of Genetics and Breeding in Forest Trees and Ornamental Plants, Ministry of Education, College of Biological Sciences and Technology, Beijing Forestry University, Beijing 100083, China
²National Engineering Research Center of Tree Breeding and Ecological Restoration, Beijing 100083, China

Received:2022-10-25 Accepted:2023-02-28 Online:2023-11-01 Published:2023-11-27
Contact: * E-mail: lixj@bjfu.edu.cn

摘要/Abstract

摘要： 点击化学又称“链接化学”或“速配结合式组合化学”。其可通过碳-杂原子键(C-X-C)连接产生出诸多功能强大、高度可靠且具较强特异性的反应, 是一种快速合成大量化合物的新方法。近几年, 点击化学在药物开发、新材料合成、材料表面功能化修饰和生物大分子标记等方面取得了较大进展。2022年, 点击化学的开拓者获得了诺贝尔化学奖。该文简要介绍点击化学的原理和反应类型, 重点总结其在标记生物大分子上的研究进展, 特别是在植物细胞壁聚糖标记方面的应用, 以期为解析植物细胞壁结构、合成和动态转运机制提供新思路。

关键词: 点击化学反应, 叠氮-炔烃环加成反应, 细胞壁, 聚糖

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

张御格, 袁笑妍, 张贵芳, 李雨健, 殷金环, 林金星, 李晓娟. 点击化学反应在植物细胞标记中的应用. 植物学报, 2023, 58(6): 956-965.

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

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链接本文: https://www.chinbullbotany.com/CN/10.11983/CBB22252

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

图/表 3

图1 环加成反应的2种反应类型CuAAC (A)和SPAAC (B) CuAAC采用端基炔烃和叠氮化物在铜离子催化下形成1,4-二取代-1,2,3-三唑; SPAAC利用环辛炔和叠氮化物反应形成稳定的三唑。CuAAC: 铜(I)催化的叠氮-炔烃环化加成反应; SPAAC: 张力促进的叠氮-炔烃环化加成反应

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

图2 点击化学标记在细胞壁聚糖中应用流程图图中非天然糖指细胞壁中的单糖组分, 不特指具体糖类。① 外源单糖类似物通过聚糖合成的补救途径代谢进入细胞; ② 含荧光团的探针与沉积在细胞壁上并含有单糖类似物的聚糖发生点击反应; ③ 荧光成像检测单糖类似物在植物体内的排布, 如下方荧光成像图所示植物细胞壁中的果胶RG-II; ④ 荧光显微镜成像点击化学标记的果胶在植物根中的排布(bar=50 μm)。

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).

表1 拟南芥中含有炔基或叠氮官能团的糖类似物

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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点击化学反应在植物细胞标记中的应用

The Application of Click Chemistry Reactions in Plant Cell Labeling

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