A Chemoenzymatic Cascade Combining a Hydration Catalyst with an Amine Dehydrogenase: Synthesis of Chiral Amines

被引:24
作者
Chang, Fengwei [1 ]
Wang, Chengyi [1 ]
Chen, Qipeng [1 ]
Zhang, Yongjin [1 ]
Liu, Guohua [1 ]
机构
[1] Shanghai Normal Univ, Int Joint Lab Resource Chem & Engn Res Ctr Green, Shanghai 200234, Peoples R China
关键词
amine dehydrogenase; asymmetric catalysis; hydration; mesoporous materials; reductive amination; ASYMMETRIC-SYNTHESIS; REDUCTIVE AMINATION; PIVOTAL ROLE; COMPLEXES; ALCOHOLS;
D O I
10.1002/anie.202114809
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The combination of biocatalysis and transition-metal catalysis can complement synthetic gaps only in a chemical or biological process. However, the intrinsic mutual deactivation between enzymatic and chemical species is a significant challenge in a single operation. To address the above issue, we developed an encapsulated Au/carbene combined with a free amine dehydrogenase as a co-catalyst system that enables an efficient hydration/amination enantioselective cascade process to be accomplished. The mechanistic investigation discloses dual catalysis comprised of alkyne hydration, followed by a reductive amination process.
引用
收藏
页数:5
相关论文
共 29 条
  • [1] Integrating Au Catalysis and Engineered Amine Dehydrogenase for the Chemoenzymatic Synthesis of Chiral Aliphatic Amines
    Liu, Jianqiao
    Bai, Jing
    Liu, Yunting
    Zhou, Liya
    He, Ying
    Ma, Li
    Liu, Guanhua
    Gao, Jing
    Jiang, Yanjun
    JACS AU, 2024, 4 (06): : 2281 - 2290
  • [2] Development of an Amine Dehydrogenase for Synthesis of Chiral Amines
    Abrahamson, Michael J.
    Vazquez-Figueroa, Eduardo
    Woodall, Nicholas B.
    Moore, Jeffrey C.
    Bommarius, Andreas S.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (16) : 3969 - 3972
  • [3] Synthesis of Chiral Amines via a Bi-Enzymatic Cascade Using an Ene-Reductase and Amine Dehydrogenase
    Jongkind, Ewald P. J.
    Fossey-Jouenne, Aurelie
    Mayol, Ombeline
    Zaparucha, Anne
    Vergne-Vaxelaire, Carine
    Paul, Caroline E.
    CHEMCATCHEM, 2022, 14 (02)
  • [4] The Evolution of an Amine Dehydrogenase Biocatalyst for the Asymmetric Production of Chiral Amines
    Abrahamson, Michael J.
    Wong, John W.
    Bommarius, Andreas S.
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (09) : 1780 - 1786
  • [5] Kinetic Resolution of Racemic Amines to Enantiopure (S)-amines by a Biocatalytic Cascade Employing Amine Dehydrogenase and Alanine Dehydrogenase
    Patil, Mahesh D.
    Yoon, Sanghan
    Jeon, Hyunwoo
    Khobragade, Taresh P.
    Sarak, Sharad
    Pagar, Amol D.
    Won, Yumi
    Yun, Hyungdon
    CATALYSTS, 2019, 9 (07):
  • [6] Engineering the substrate acceptance of l-amine dehydrogenase enables the collective biocatalytic synthesis of N-heterocyclic primary amines
    Wu, Tao
    Xu, Yan
    Nie, Yao
    Mu, Xiaoqing
    CHEMICAL ENGINEERING JOURNAL, 2024, 490
  • [7] Amine transaminases in chiral amines synthesis: recent advances and challenges
    Ferrandi, Erica E.
    Monti, Daniela
    WORLD JOURNAL OF MICROBIOLOGY & BIOTECHNOLOGY, 2018, 34 (01)
  • [8] Merging Gold(I) Catalysis with Amine Transaminases in Cascade Catalysis: Chemoenzymatic Transformation of Propargylic Alcohols into Enantioenriched Allylic Amines
    Gonzalez-Granda, Sergio
    Tzouras, Nikolaos, V
    Nolan, Steven P.
    Lavandera, Ivan
    Gotor-Fernandez, Vicente
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (22) : 3856 - 3866
  • [9] Deracemization of Racemic Amines to Enantiopure (R)- and (S)-amines by Biocatalytic Cascade Employing ω-Transaminase and Amine Dehydrogenase
    Yoon, Sanghan
    Patil, Mahesh D.
    Sarak, Sharad
    Jeon, Hyunwoo
    Kim, Geon-Hee
    Khobragade, Taresh P.
    Sung, Sihyong
    Yun, Hyungdon
    CHEMCATCHEM, 2019, 11 (07) : 1898 - 1902
  • [10] Asymmetric Synthesis of Chiral Halogenated Amines using Amine Transaminases
    Dawood, Ayad W. H.
    de Souza, Rodrigo O. M. A.
    Bornscheuer, Uwe T.
    CHEMCATCHEM, 2018, 10 (05) : 951 - 955