Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, China.
Asymmetric Synthesis and Chiral Technology Key Laboratory of Sichuan Province, Department of Chemistry, Xihua University, Chengdu, 610039, China.
Chempluschem. 2023 Jun;88(6):e202300138. doi: 10.1002/cplu.202300138.
The first near IR fluorescent probe for the chemoselective and enantioselective recognition of arginine in aqueous solution is reported in this work. This probe, made of a 1,1'-binaphthyl-based chiral aldehyde unit and a rhodamine-based near IR chromophore, in combination with La exhibits highly chemoselective as well as enantioselective fluorescent enhancement with arginine at λ=764 nm upon excitation at λ=690 nm. Little or no fluorescent response is observed toward the chirality miss-matched arginine enantiomer or other common amino acids and their enantiomers. This probe also allows visual discrimination of the arginine enantiomers because of its fast and distinct color change upon interaction with the substrate.
本工作报道了首例用于水溶液中精氨酸的化学选择性和对映选择性识别的近红外荧光探针。该探针由基于 1,1'-联萘的手性醛单元和基于罗丹明的近红外发色团组成，与镧（La）结合后，在 690nm 激发时，对精氨酸表现出高度的化学选择性和对映选择性荧光增强，在 764nm 处检测到。对与手性错配的精氨酸对映体或其他常见氨基酸及其对映体几乎没有或没有荧光响应。由于与底物相互作用后快速且明显的颜色变化，该探针还可以用于视觉区分精氨酸对映体。
