Citation: Chuan-Zhi Ni, Ruo-Ming Li, Fang-Qi Zhang, Qu-Ao-Wei Li, Yuan-Yuan Zhu, Jie Zeng, Shuang-Xi Gu. A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells[J]. Chinese Chemical Letters, ;2024, 35(10): 109862. doi: 10.1016/j.cclet.2024.109862 shu

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

Chuan-Zhi Ni ^{a, 1} ,
Ruo-Ming Li ^{a, b, 1} ,
Fang-Qi Zhang ^a ,
Qu-Ao-Wei Li ^a ,
Yuan-Yuan Zhu ^{a, *,} ,
Jie Zeng ^{a, *,} ,
Shuang-Xi Gu ^{a, *,}

a.
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
b.
Nanjing Pusheng Biomedical Co., Ltd., Nanjing 210033, China

yyzhu531@163.com

jiezeng116964@163.com

shuangxigu@163.com

Received Date: 17 February 2024
Revised Date: 29 March 2024
Accepted Date: 6 April 2024
Available Online: 29 April 2024

Figures(10)

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.
- Fluorescent probe,
- Chiral recognition,
- Enantioselectivity,
- Chemoselectivity,
- Basic amino acids,
- Cell imaging
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