Porphyrin-Based Metal–Organic Frameworks for Efficient Electrochemiluminescent Chiral Recognition of Tyrosine Enantiomers

• Published in: Chemosensors Vol. 10; no. 12; p. 519
• Main Authors: Cai, Wen-Rong, Zhu, Wen-Kai, Yang, Bao-Zhu, Wu, Da-Tong, Li, Jun-Yao, Yin, Zheng-Zhi, Kong, Yong
• Format: Journal Article
• Language: English
• Published: Basel MDPI AG 01-12-2022
• Subjects: Amino acids; Biomedical materials; Chemical reduction; Chemical tests and reagents; chiral recognition; Chromatography; Density functional theory; Density functionals; Electrochemiluminescence; Electrodes; Emitters; Enantiomers; Hydrogen; Hydrogen bonding; Hydrogen bonds; meso-tetra(4-carboxyphenyl)porphine; Metabolism; Metal-organic frameworks; metal–organic framework; Phenols; Porphyrins; Reagents; Recognition; Scientific imaging; Sensors; Tyrosine; Zinc; Zinc compounds; China; United Kingdom > UK; Japan; Germany
• ISSN: 2227-9040; 2227-9040
• DOI: 10.3390/chemosensors10120519

Science the biological activities of chiral enantiomers are often different or even opposite, their chiral recognition is of great significance. A new assembly structure named TCPP-Zn-(S)-BINOL was obtained based on the interaction between chiral binaphthol (BINOL) and the porphyrin-based MOF structure formed by Meso-Tetra(4-carboxyphenyl)porphine (TCPP) and Zn2+, and a new chiral sensor was designed relying on TCPP-Zn-(S)-BINOL. The chiral platform was designed by using binaphthol as a chiral recognizer and the porphyrin MOF as an emitter, which can recognize tyrosine (Tyr) enantiomers via the electrochemiluminescence (ECL) method. According to density functional theory (DFT), TCPP-Zn-(S)-BINOL has a different affinity with L/D-Tyr due to the different strength of the hydrogen bond between chiral ligand BINOL and the tyrosine (Tyr) enantiomer. It will be more suitable for combination with L-Tyr, and the presence of L-Tyr will increase the ECL intensity of the modified electrode via the catalytic reduction of co-reactant reagents, achieving the purpose of the chiral recognition of Tyr enantiomers. These findings show that TCPP-Zn-(S)-BINOL can be used as an advanced ECL chiral recognition platform for biomedical applications.