15N-amino acids, labeled with the 15N isotope, are valuable tools for studying natural product synthesis, protein metabolism, and disease diagnosis and treatment. They are also essential in the production of 15N-labeled drugs.
Traditionally, 15N-labeled amino acids have been synthesized through microbial fermentation and chemical reduction amination of ketoacids. However, these methods are complex, require high temperatures, and often involve the use of toxic cyanide, which poses energy and environmental challenges. Therefore, the development of a green and mild method for synthesizing 15N-amino acids is crucial.
In a recent study conducted by Zhang’s group, an electrochemical method was employed to synthesize 15N-amino acids from 15N-nitrite and ketonic acids using a commercial nickel foam (NF) cathode in an aqueous solution under ambient conditions. The researchers achieved a 93% yield of 15N-alanine. Notably, the major byproduct, 15N-ammonium, could be electrooxidized back to 15N-nitrite with a yield of 93%, resulting in the recycling and atomic economy of 15N-nitrite. The findings were published in the journal Science China Chemistry.
A series of control experiments, in situ attenuated total reflection Fourier transform infrared spectroscopy, and online differential electrochemical mass spectrometry revealed a 15N-nitrite→15NH2OH→15N-oxime→15N-amino acid pathway. Furthermore, the method proved effective in synthesizing six different 15N-amino acids with yields ranging from 68% to 95%, demonstrating its universality. The researchers also successfully synthesized a hepatitis treatment drug, 15N-tiopronin, using 15N-glycine, highlighting the method’s utility.
This study not only presents a strategy for the green synthesis of 15N-amino acids at room temperature but also opens up sustainable possibilities for the construction of 15N-labeled compounds.
More information:
Yongmeng Wu et al, Electrosynthesis of 15N-labeled amino acids from 15N-nitrite and ketonic acids, Science China Chemistry (2023). DOI: 10.1007/s11426-023-1613-x
Citation:
Study offers strategy for green synthesis of 15N-amino acids (2023, June 30)
retrieved 30 June 2023
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