Proximity Histidine Labeling by Umpolung Strategy Using Singlet Oxygen,Journal of the American Chemical Society

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Proximity Histidine Labeling by Umpolung Strategy Using Singlet Oxygen
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2021-04-27 , DOI: 10.1021/jacs.1c01626
Keita Nakane ₁ , Shinichi Sato _{1,

2} , Tatsuya Niwa ₃ , Michihiko Tsushima ₄ , Shusuke Tomoshige ₁ , Hideki Taguchi ₃ , Minoru Ishikawa ₁ , Hiroyuki Nakamura ₄

Affiliation

While electrophilic reagents for histidine labeling have been developed, we report an umpolung strategy for histidine functionalization. A nucleophilic small molecule, 1-methyl-4-arylurazole, selectively labeled histidine under singlet oxygen (¹O₂) generation conditions. Rapid histidine labeling can be applied for instant protein labeling. Utilizing the short diffusion distance of ¹O₂ and a technique to localize the ¹O₂ generator, a photocatalyst in close proximity to the ligand-binding site, we demonstrated antibody Fc-selective labeling on magnetic beads functionalized with a ruthenium photocatalyst and Fc ligand, ApA. Three histidine residues located around the ApA binding site were identified as labeling sites by liquid chromatography–mass spectrometry analysis. This result suggests that ¹O₂-mediated histidine labeling can be applied to a proximity labeling reaction on the nanometer scale.

中文翻译：

使用单线态氧通过 Umpolung 策略进行邻近组氨酸标记

虽然已经开发了用于组氨酸标记的亲电试剂，但我们报告了组氨酸功能化的 umpolung 策略。亲核小分子 1-methyl-4-arylurazole，在单线态氧 ( ¹ O ₂ ) 生成条件下选择性标记组氨酸。快速组氨酸标记可用于即时蛋白质标记。利用¹ O ₂的短扩散距离和定位¹ O _{2 的技术}发电机，一种靠近配体结合位点的光催化剂，我们在用钌光催化剂和 Fc 配体 ApA 功能化的磁珠上证明了抗体 Fc 选择性标记。通过液相色谱-质谱分析，位于 ApA 结合位点周围的三个组氨酸残基被鉴定为标记位点。该结果表明¹ O ₂介导的组氨酸标记可以应用于纳米尺度的邻近标记反应。

更新日期：2021-05-26

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