A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells  

作　　者：Chuan-Zhi Ni Ruo-Ming Li Fang-Qi Zhang Qu-Ao-Wei Li Yuan-Yuan Zhu Jie Zeng Shuang-Xi Gu 

机构地区：[1]School of Chemistry and Environmental Engineering,School of Chemical Engineering&Pharmacy,Pharmaceutical Research Institute,Hubei Key Laboratory of Novel Reactor and Green Chemical Technology,Wuhan Institute of Technology,Wuhan 430205,China [2]Nanjing Pusheng Biomedical Co.,Ltd.,Nanjing 210033,China

出　　处：《Chinese Chemical Letters》2024年第10期364-369,共6页中国化学快报（英文版）

基　　金：financial support from the National Natural Science Foundation of China(Nos.22074114,22377097,21877087);Natural Science Foundation of Hubei Province of China(Nos.2020CFB623,2021CFB556);Engineering Research Center of Phosphorus Resources Development and Utilization of Ministry of Education(No.LCX202305);Wuhan Institute of Technology Graduate Education and Teaching Reform Research Project(Nos.2022JYXM09,2021JYXM07);Wuhan Institute of Technology Graduate Innovation Fund(No.CX2022450)are greatly appreciated。

摘　　要：A novel and readily available binaphthyl-based fluorescent probe(S)-1 was designed and synthesized.(S)-1 can be used to not only chemoselectively discriminate 3 basic amino acids out of common amino acids,but also enantioselectively recognize histidine.Encouragingly,enantioselective imaging of histidine in cells was achieved for the first time by the probe(S)-1.These performances endowed it potential application in the chiral analysis of basic amino acids in asymmetric synthesis and cell imaging for diagnosis of diseases caused by racemization of histidine.Nuclear magnetic resonance(NMR)and mass spectrometry investigations suggested that different reaction extent of(S)-1 with L/D-histidine and different product structures generated the observed enantioselective fluorescent response.The molecular structures and thermodynamic stability of the complexes,formed from(S)-1+Zn2+and enantiomers of histidine,were calculated by Gaussian 16 based on density functional theory(DFT)to validate the above action mechanism.

关 键 词：Fluorescent probe Chiral recognition ENANTIOSELECTIVITY CHEMOSELECTIVITY Basic amino acids Cell imaging 

分 类 号：Q503[生物学—生物化学] O657.3[理学—分析化学]