Electrosynthesis ofN-labeled amino acids fromN-nitrite and ketonic acids

被引:0
作者
Yongmeng Wu [1 ]
Mengyang Li [1 ]
Tieliang Li [1 ]
Jinghui Zhao [1 ]
Ziyang Song [1 ]
Bin Zhang [1 ,2 ]
机构
[1] Department of Chemistry, School of Science, Institute of Molecular Plus, Tianjin University
[2] Tianjin Key Laboratory of Molecular Optoelectronic Science, Key Laboratory of Systems Bioengineering (Ministry of Education), Tianjin University
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中图分类号
TQ460.1 [基础理论];
学科分类号
1007 ;
摘要
15N isotope-labeled amino acids(15N-amino acids) are crucial in the fields of biology, medicine, and chemistry. 15N-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 15N-amino acids from readily available 15N-nitrite(15NO2-)and biomass-derived ketonic acids under ambient conditions driven by renewable electricity. A mechanistic study demonstrates a 15N-nitrite→ 15NH2OH→ 15N-pyruvate oxime→ 15N-alanine reaction pathway for 15N-alanine synthesis. Moreover, this electrochemical strategy can synthesize six 15N-amino acids with 68%–95% yields. Furthermore, a 15N-labeled drug of 15N-tiopronin,the most commonly used hepatitis treatment drug, is fabricated using 15N-glycine as the building block. Impressively, 15N sources can be recycled by the electrooxidation of 15NH4+to 15NO2-with a method economy. This work opens an avenue for the green synthesis of 15N-labeled compounds or drugs.
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页码:1854 / 1859
页数:6
相关论文
共 21 条
[1]  
Li Junnan,Zhang Yuxuan,Kuruvinashetti Kiran,Kornienko Nikolay.Construction of C–N bonds from small-molecule precursors through heterogeneous electrocatalysis[J].Nature Reviews Chemistry,2022
[2]   Electrochemically driven C-N bond formation from CO2 and ammonia at the triple-phase boundary [J].
Li, Junnan ;
Kornienko, Nikolay .
CHEMICAL SCIENCE, 2022, 13 (14) :3957-3964
[3]   Insertion of ammonia into alkenes to build aromatic N-heterocycles [J].
Liu, Shuai ;
Cheng, Xu .
NATURE COMMUNICATIONS, 2022, 13 (01)
[4]   Direct electrosynthesis of methylamine from carbon dioxide and nitrate [J].
Wu, Yueshen ;
Jiang, Zhan ;
Lin, Zhichao ;
Liang, Yongye ;
Wang, Hailiang .
NATURE SUSTAINABILITY, 2021, 4 (08) :725-+
[5]  
Liu Xu,Liu Ruoyu,Qiu Jiaxing,Cheng Xu,Li Guigen.Chemical-Reductant-Free Electrochemical Deuteration Reaction using Deuterium Oxide[J].Angewandte Chemie (International ed. in English),2020
[6]  
Wu Yongmeng,Liu Cuibo,Wang Changhong,Lu Siyu,Zhang Bin.Selective Transfer Semihydrogenation of Alkynes with H2O (D2O) as the H (D) Source over a Pd-P Cathode[J].Angewandte Chemie (International ed. in English),2020
[7]  
Fukushima Takashi,Yamauchi Miho.Electrosynthesis of amino acids from biomass-derivable acids on titanium dioxide[J].Chemical communications (Cambridge, England),2019
[8]   NMR-based metabolite studies with 15N amino acids [J].
Ramirez, Benjamin ;
Durst, Matthew A. ;
Lavie, Arnon ;
Caffrey, Michael .
SCIENTIFIC REPORTS, 2019, 9 (1)
[9]   Applications of Deuterium in Medicinal Chemistry [J].
Pirali, Tracey ;
Serafini, Marta ;
Cargnin, Sarah ;
Genazzani, Armando A. .
JOURNAL OF MEDICINAL CHEMISTRY, 2019, 62 (11) :5276-5297
[10]  
Sebastian Lips,Prof. Dr. Siegfried R. Waldvogel.Use of Boron‐Doped Diamond Electrodes in Electro‐Organic Synthesis[J].ChemElectroChem,2019