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

被引:28
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 30 条
[1]   Integrating Au Catalysis and Engineered Amine Dehydrogenase for the Chemoenzymatic Synthesis of Chiral Aliphatic Amines [J].
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 [J].
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 [J].
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 [J].
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 [J].
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 [J].
Wu, Tao ;
Xu, Yan ;
Nie, Yao ;
Mu, Xiaoqing .
CHEMICAL ENGINEERING JOURNAL, 2024, 490
[7]   Amine transaminases in chiral amines synthesis: recent advances and challenges [J].
Ferrandi, Erica E. ;
Monti, Daniela .
WORLD JOURNAL OF MICROBIOLOGY & BIOTECHNOLOGY, 2018, 34 (01)
[8]   Unlocking the Substrate Acceptance of Phenylalanine Amine Dehydrogenase Enables the Asymmetric Synthesis of Pharmaceutical N-Heterocyclic Primary Amines [J].
Wu, Tao ;
Nie, Yao ;
Xu, Jiaxing ;
Mu, Xiaoqing .
ACS CATALYSIS, 2024, 15 (02) :877-888
[9]   Merging Gold(I) Catalysis with Amine Transaminases in Cascade Catalysis: Chemoenzymatic Transformation of Propargylic Alcohols into Enantioenriched Allylic Amines [J].
Gonzalez-Granda, Sergio ;
Tzouras, Nikolaos, V ;
Nolan, Steven P. ;
Lavandera, Ivan ;
Gotor-Fernandez, Vicente .
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (22) :3856-3866
[10]   Deracemization of Racemic Amines to Enantiopure (R)- and (S)-amines by Biocatalytic Cascade Employing ω-Transaminase and Amine Dehydrogenase [J].
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