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
  • [21] Amine-Tolerant E. coli Strains Generated via Adaptive Evolution for Sustainable Synthesis of Chiral Amines
    Mendoza-Avila, Josemarco
    Doring, Volker
    Bouzon, Madeleine
    Dubois, Ivan
    Knaus, Tanja
    Mouterde, Louis M. M.
    Zaparucha, Anne
    Mutti, Francesco G.
    Vergne-Vaxelaire, Carine
    [J]. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2024, 12 (39): : 14435 - 14445
  • [22] Construction of an enzymatic-chemical cascade involving engineered amine dehydrogenases for the synthesis of chiral non-α-amino acids by substrate engineering and enzyme evolution
    Lai, Zhuofan
    Wu, Tao
    Zhou, Feng
    Xu, Yan
    Mu, Xiaoqing
    [J]. MOLECULAR CATALYSIS, 2024, 559
  • [23] Direct Cyclic Carbonate Synthesis from CO2 and Diol over Carboxylation/Hydration Cascade Catalyst of CeO2 with 2-Cyanopyridine
    Honda, Masayoshi
    Tamura, Masazumi
    Nakao, Kenji
    Suzuki, Kimihito
    Nakagawa, Yoshinao
    Tomishige, Keiichi
    [J]. ACS CATALYSIS, 2014, 4 (06): : 1893 - 1896
  • [24] A Palladium/Chiral Amine Co-catalyzed Enantioselective Dynamic Cascade Reaction: Synthesis of Polysubstituted Carbocycles with a Quaternary Carbon Stereocenter
    Ma, Guangning
    Afewerki, Samson
    Deiana, Luca
    Palo-Nieto, Carlos
    Liu, Leifeng
    Sun, Junliang
    Ibrahem, Ismail
    Cordova, Armando
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (23) : 6050 - 6054
  • [25] A One-Pot Cascade Reaction Combining an Encapsulated Decarboxylase with a Metathesis Catalyst for the Synthesis of Bio-Based Antioxidants
    Baraibar, Alvaro Gomez
    Reichert, Dennis
    Muegge, Carolin
    Seger, Svenja
    Groeger, Harald
    Kourist, Robert
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (47) : 14823 - 14827
  • [26] Asymmetric synthesis of chiral cyclic amine from cyclic imine by bacterial whole-cell catalyst of enantioselective imine reductase
    Mitsukura, Koichi
    Suzuki, Mai
    Tada, Kazuhiro
    Yoshida, Toyokazu
    Nagasawa, Toru
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (20) : 4533 - 4535
  • [27] Bifunctional iridium-(2-aminoterephthalate)-Zr-MOF chemoselective catalyst for the synthesis of secondary amines by one-pot three-step cascade reaction
    Pintado-Sierra, Mercedes
    Rasero-Almansa, Antonia M.
    Corma, Avelino
    Iglesias, Marta
    Sanchez, Felix
    [J]. JOURNAL OF CATALYSIS, 2013, 299 : 137 - 145
  • [28] A novel D-mandelate dehydrogenase used in three-enzyme cascade reaction for highly efficient synthesis of non-natural chiral amino acids
    Fan, Chang-Wei
    Xu, Guo-Chao
    Ma, Bao-Di
    Bai, Yun-Peng
    Zhang, Jie
    Xu, Jian-He
    [J]. JOURNAL OF BIOTECHNOLOGY, 2015, 195 : 67 - 71
  • [29] Biocatalytic Approaches towards the Synthesis of Chiral Amino Alcohols from Lysine: Cascade Reactions Combining alpha-Keto Acid Oxygenase Hydroxylation with Pyridoxal Phosphate- Dependent Decarboxylation
    Baud, Damien
    Peruch, Olivier
    Saaidi, Pierre-Loic
    Fossey, Aurelie
    Mariage, Aline
    Petit, Jean-Louis
    Salanoubat, Marcel
    Vergne-Vaxelaire, Carine
    de Berardinis, Veronique
    Zaparucha, Anne
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (09) : 1563 - 1569