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Readily Accessible and Brightly Fluorogenic BODIPY/NBD–Tetrazines via SNAr Reactions
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2024-04-10 , DOI: 10.1021/acs.joc.3c02864
Murat Işık 1 , Mehmet Ali Kısaçam 2
Affiliation  

We describe SNAr reactions of some commercial amino-tetrazines and halo-dyes, which give efficiently quenched BODIPY/NBD–tetrazines (ΦFl < 0.01) in high yields and, importantly, with high purities affordable via simple silica gel chromatography only. The dyes exhibit large Stokes shifts, moderate environmental sensitivity, and emission enhancements (up to 193-fold) upon Tz ligation with BCN─a strained dienophile. They successfully serve as labels for HSA protein premodified with BCN, resulting in bright blue–green emission upon ligation.

中文翻译:

通过 SNAr 反应可轻松获得且明亮的荧光 BODIPY/NBD-四嗪

我们描述了一些商业氨基四嗪和卤代染料的 SNA Ar 反应,这些反应以高产率有效淬灭 BODIPY/NBD-四嗪 ( Φ Fl < 0.01),重要的是,仅通过简单的硅胶色谱即可获得高纯度。这些染料在与 BCN(一种应变亲双烯体)Tz 连接后表现出较大的斯托克斯位移、中等环境敏感性和发射增强(高达 193 倍)。它们成功地作为用 BCN 预修饰的 HSA 蛋白的标记,在连接时产生明亮的蓝绿色发射。
更新日期:2024-04-11
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