Direct ring-strain loading for visible-light accelerated bioorthogonal ligation via diarylsydnone-dibenzo[b,f ][1,4,5]thiadiazepine photo-click reactions

作者：Jingshuo Gao, Qin Xiong, Xueting Wu, Jiajie Deng, Xiaocui Zhang, Xiaohu Zhao, Pengchi Deng, Zhipeng Yu · 发表于：Communications Chemistry · 年份：2020 · DOI：10.1038/s42004-020-0273-6 · 被引用次数：44 · 研究领域：Click Chemistry and Applications、Chemical Synthesis and Analysis、Advanced biosensing and bioanalysis techniques

Ultra-fast and selective covalent-bond forming reactions with spatiotemporal controllability are foundational for developing a bioorthogonal approach with high manipulability. However, it is challenging to exploit a reporter functional group to achieve these requirements simultaneously. Here, 11H-Dibenzo[c,f][1,2]diazepine and a set of heterocyclic analogues are investigated for both their photo-switching natures and their ability to serve as dipolarophiles in photo-click reactions with diarylsydnone. Sulfur-containing dibenzothiadiazepine (DBTD) is discovered to be an excellent chemical reporter in cycloaddition with visible-light excitation for in-situ ring-strain loading via its (Z) → (E) photo-isomerization. The bioorthogonal utility of the DBTD tag in spatiotemporally controlled ligation for protein modifications on live cells is also demonstrated.