Photoredox Microfluidic Synthesis of Trifluoromethylated Amino Acids

被引:5
|
作者
Liu, Jiyang [1 ]
Zhang, Weigang [1 ]
Tao, Xiangzhang [1 ]
Wang, Qing [1 ]
Wang, Xiaochen [1 ]
Pan, Yi [1 ]
Ma, Jinzhu [2 ]
Yan, Liang [1 ,2 ]
Wang, Yi [1 ]
机构
[1] Nanjing Univ, Collaborat Innovat Ctr Adv Microstruct, Sch Chem & Chem Engn, State Key Lab Coordinat Chem,Jiangsu Key Lab Adv O, Nanjing 210023, Peoples R China
[2] Wannan Med Coll, Sch Basic Med, Wuhu 241000, Peoples R China
基金
中国国家自然科学基金; 中国博士后科学基金;
关键词
MEDICINAL CHEMISTRY; FLUORINE; 4-ALKYL-1,4-DIHYDROPYRIDINES; DERIVATIVES; ALKYLATION; DESIGN; IMINES; ESTERS;
D O I
10.1021/acs.orglett.3c00915
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Fluorinated amino acids are a class of highly valuable building blocks that are widely employed in biological science and pharmaceutical industry for improved stability, activity, and folding property of proteins. However, the synthetic approach has conventionally been constrained by harsh conditions and limited substrate range. We demonstrate a general synthetic protocol for photoinduced alpha-CF3 amino acids using continuous flow technology that benefits from enhanced fusion and precise control of reaction time, making it potentially useful in large-scale peptide synthesis.
引用
收藏
页码:3083 / 3088
页数:6
相关论文
共 50 条
  • [41] The synthesis of "amino acids".
    Knoop, F
    Hoessli, H
    BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1906, 39 : 1477 - 1480
  • [42] Trifluoroacetaldehyde: A useful industrial bulk material for the synthesis of trifluoromethylated amino compounds
    Mimura, Hideyuki
    Kawada, Kosuke
    Yamashita, Tetsuya
    Sakamoto, Takeshi
    Kikugawa, Yasuo
    JOURNAL OF FLUORINE CHEMISTRY, 2010, 131 (04) : 477 - 486
  • [43] Terahertz characteristics of amino acids based on microfluidic technology
    Ye, Ping
    Yang, Yizhou
    Su, Bo
    Zhang, Cunlin
    AOPC 2021: INFRARED DEVICE AND INFRARED TECHNOLOGY, 2021, 12061
  • [44] SYNTHESIS OF ENANTIOMERICALLY ENRICHED ALPHA-TRIFLUOROMETHYLATED ACIDS, ESTERS AND KETONES
    WATANABE, S
    SHIMADA, Y
    KITAZUME, T
    YAMAZAKI, T
    JOURNAL OF FLUORINE CHEMISTRY, 1992, 59 (02) : 249 - 256
  • [45] Visible Light-Induced Photoredox Construction of Trifluoromethylated Quaternary Carbon Centers from Trifluoromethylated Tertiary Bromides
    Huan, Feng
    Chen, Qing-Yun
    Guo, Yong
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (16): : 7051 - 7063
  • [46] Modular synthesis of β-amino acids from alkenes, amines, and CO2 via photoredox/copper dual catalysis
    Lei Song
    Jie Wu
    Science China(Chemistry), 2024, (06) : 1756 - 1757
  • [47] Modular synthesis of β-amino acids from alkenes, amines, and CO2via photoredox/copper dual catalysis
    Song, Lei
    Wu, Jie
    SCIENCE CHINA-CHEMISTRY, 2024, 67 (06) : 1756 - 1757
  • [48] Synthesis of Aldehydic Ribonucleotide and Amino Acid Precursors by Photoredox Chemistry
    Ritson, Dougal J.
    Sutherland, John D.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (22) : 5845 - 5847
  • [50] Chemical Modification of Dehydrated Amino Acids in Natural Antimicrobial Peptides by Photoredox Catalysis
    de Bruijn, A. Dowine
    Roelfes, Gerard
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (44) : 11314 - 11318