Electrosynthesis of ^(15)N-labeled amino acids from ^(15)N-nitrite and ketonic acids  

作　　者：Yongmeng Wu Mengyang Li Tieliang Li Jinghui Zhao Ziyang Song Bin Zhang 

机构地区：[1]Department of Chemistry,School of Science,Institute of Molecular Plus,Tianjin University,Tianjin 300072,China [2]Tianjin Key Laboratory of Molecular Optoelectronic Science,Key Laboratory of Systems Bioengineering(Ministry of Education),Tianjin University,Tianjin 300072,China

出　　处：《Science China Chemistry》2023年第6期1854-1859,共6页中国科学（化学英文版）

基　　金：supported by the National Natural Science Foundation of China(22271213);the National Postdoctoral Science Foundation of China(2022M722357)。

摘　　要：^(15)N isotope-labeled amino acids(^(15)N-amino acids)are crucial in the fields of biology,medicine,and chemistry.^(15)N-amino acids are conventionally synthesized through microbial fermentation and chemical reductive amination of ketonic acids methodologies,which usually require complicated procedures,high temperatures,or toxic cyanide usage,causing energy and environmental concerns.Here,we report a sustainable pathway to synthesize ^(15)N-amino acids from readily available ^(15)N-nitrite(^(15)NO_(2)-)and biomass-derived ketonic acids under ambient conditions driven by renewable electricity.A mechanistic study demonstrates a ^(15)N-nitrite→^(15)NH_(2)OH→^(15)N-pyruvate oxime→^(15)N-alanine reaction pathway for ^(15)N-alanine synthesis.Moreover,this electrochemical strategy can synthesize six ^(15)N-amino acids with 68%–95%yields.Furthermore,a ^(15)N-labeled drug of ^(15)N-tiopronin,the most commonly used hepatitis treatment drug,is fabricated using ^(15)N-glycine as the building block.Impressively,^(15)N sources can be recycled by the electrooxidation of ^(15)NH4^(+) to ^(15)NO_(2)-with a method economy.This work opens an avenue for the green synthesis of ^(15)N-labeled compounds or drugs.

关 键 词：green synthesis ^(15)N-labeled amino acids ELECTROSYNTHESIS C-N bond isotope labeling 

分 类 号：TQ460.1[化学工程—制药化工]