Donor Amine Salt-Based Continuous in situ-Product Crystallization in Amine Transaminase-Catalyzed Reactions

被引:19
作者
Huelsewede, Dennis [1 ]
Dohm, Jan-Niklas [1 ]
von Langermann, Jan [1 ]
机构
[1] Univ Rostock, Inst Chem, Biocatalyt Synth Grp, Albert Einstein Str 3 A, D-18059 Rostock, Germany
关键词
biocatalysis; in situ-product removal; crystallization; amine; salts; ASYMMETRIC-SYNTHESIS; CHIRAL AMINE; REACTION EQUILIBRIUM; MEMBRANE; CASCADE;
D O I
10.1002/adsc.201900217
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The unfavorable reaction equilibrium of transaminase-catalyzed reactions is a major challenge for the efficient biocatalytic synthesis of chiral amines. In this study the synthetic utilization of a salt-based, continuous in situ-product crystallization is described to overcome the thermodynamic limit in amine transaminase-reactions using only the commonly used amine donor isopropylamine. The simultaneous dissolution of isopropylammonium 3,3-diphenylpropionate (donor salt) in combination with the crystallization of the product salt facilitates a thermodynamic shift of the continuous amine transaminase-catalyzed reaction. The main process necessity is a lower product salt solubility in comparison to the applied donor salt. This concept facilitates a stoichiometric use of isopropylamine in combination with a significantly lowered concentration of the amines in solution.
引用
收藏
页码:2727 / 2733
页数:7
相关论文
共 33 条
[1]   A Process Concept for High-Purity Production of Amines by Transaminase-Catalyzed Asymmetric Synthesis: Combining Enzyme Cascade and Membrane-Assisted ISPR [J].
Borner, Tim ;
Rehn, Gustav ;
Grey, Carl ;
Adlercreutz, Patrick .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2015, 19 (07) :793-799
[2]   Transaminations with isopropyl amine: equilibrium displacement with yeast alcohol dehydrogenase coupled to in situ cofactor regeneration [J].
Cassimjee, Karim Engelmark ;
Branneby, Cecilia ;
Abedi, Vahak ;
Wells, Andrew ;
Berglund, Per .
CHEMICAL COMMUNICATIONS, 2010, 46 (30) :5569-5571
[3]   Sitagliptin Manufacture: A Compelling Tale of Green Chemistry, Process Intensification, and Industrial Asymmetric Catalysis [J].
Desai, Aman A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (09) :1974-1976
[4]  
Dold S.-M., 2016, GREEN BIOCATALYSIS
[5]   Amine transaminases in chiral amines synthesis: recent advances and challenges [J].
Ferrandi, Erica E. ;
Monti, Daniela .
WORLD JOURNAL OF MICROBIOLOGY & BIOTECHNOLOGY, 2018, 34 (01)
[6]   The Industrial Age of Biocatalytic Transamination [J].
Fuchs, Michael ;
Farnberger, Judith E. ;
Kroutil, Wolfgang .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (32) :6965-6982
[7]   Biocatalytic transamination with near-stoichiometric inexpensive amine donors mediated by bifunctional mono- and di-amine transaminases [J].
Galman, James L. ;
Slabu, Iustina ;
Weise, Nicholas J. ;
Iglesias, Cesar ;
Parmeggiani, Fabio ;
Lloyd, Richard C. ;
Turner, Nicholas J. .
GREEN CHEMISTRY, 2017, 19 (02) :361-366
[8]   Transaminases for chiral amine synthesis [J].
Gomm, Andrew ;
O'Reilly, Elaine .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2018, 43 :106-112
[9]   A New Generation of Smart Amine Donors for Transaminase-Mediated Biotransformations [J].
Gomm, Andrew ;
Lewis, William ;
Green, Anthony P. ;
O'Reilly, Elaine .
CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (36) :12692-12695
[10]  
Green A.P., 2014, ANGEW CHEM, V126, P10890, DOI 10.1002/ange.201406571