Journal
RSC ADVANCES
Volume 12, Issue 19, Pages 11967-11973Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2ra00803c
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Funding
- National Natural Science Foundation of China [21462018, 21861025]
- Science Fund of the Technology Office of Jiangxi, China [20192BAB203003]
- Jiangxi Science and Technology Normal University Program for Graduate Innovation Fund [YC2020-X21]
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Phenylalanine is an essential amino acid for humans and animals, and its different configurations have different activities. This research successfully synthesized a chiral fluorescent sensor that can selectively detect phenylalanine.
Phenylalanine an essential aromatic amino acid for humans and animals, cannot be synthesized by humans and animals on their own. However, it synthesizes important neurotransmitters and hormones in the body and is involved in gluconeogenesis and lipid metabolism. Moreover, the two opposite configurations of phenylalanine have different activities. For example, l-phenylalanine is a biologically active optical isomer involved in crucial biological processes, the lack of which will lead to intellectual disability, while d-phenylalanine only acts as a chiral intermediate. In this research, an H-8-BINOL chiral fluorescent sensor modified with 1,2,3-triazole was synthesized in high yield (95%) by nucleophilic substitution and click reaction. The chiral fluorescent sensor showed high enantioselectivity toward phenylalanine. l-Phenylalanine enhanced the fluorescence response of the probe significantly, while d-phenylalanine had no obvious fluorescence response change. The enantioselective fluorescence enhancement ratio [ef = (I-L - I-0)/(I-D - I-0), where I-0 is the fluorescence of the sensor without amino acids] for the highest fluorescence intensity at 20.0 equivalents of amino acids was 104.48. In this way, the probe could be used to identify and differentiate different configurations of phenylalanine.
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