Biocatalytic Transamination for the Asymmetric Synthesis of Pyridylalkylamines. Structural and Activity Features in the Reactivity of Transaminases
作者： María López-Iglesias , Daniel González-Martínez , Vicente Gotor , Eduardo Busto , Wolfgang Kroutil
关键词: Enantiopure drug 、 Enantioselective synthesis 、 Biocatalysis 、 Reactivity (chemistry) 、 Chemistry 、 Stereochemistry 、 Transamination 、 Stereoselectivity 、 Ketone 、 Amination
摘要: A set of transaminases has been investigated for the biocatalytic amination 1-(4-chloropyridin-2-yl)alkan-1-ones. The influence chain length n-1-alkanone at C-2 position pyridine studied in reaction with different (R)- and (S)-selective transaminases. Thus, enantiopure amines were isolated high purity starting from a wide selection prochiral ketones. On one hand, excellent yields (from 97 to >99% conversion, up 93% yield) stereoselectivity values (>99% ee both amine enantiomers) found linear short substituents such as ethanone or propanone. other more hindered substrates accepted only when using evolved enzymes an variant (R)-Arthrobacter (ArRmut11-TA). An initial common structural feature was presence chlorine atom on C-4 core, which increase reactivity ketone, giving extra versatility intro...
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Thomas C Nugent, Chiral amine synthesis : methods, developments and applications Wiley-VCH Verlag GmbH & Co. KGaA. ,(2010) , 10.1002/9783527629541
R. Mendoza-Meroño, S. García-Granda, R. Soria-Martínez, Synthesis, crystal structure, spectroscopic characterization and theoretical study of (2E)-N-phenyl-2-(pyridin-3-ylmethylidene)hydrazinecarboxamide Journal of Molecular Structure. ,vol. 1105, pp. 322- 331 ,(2016) , 10.1016/J.MOLSTRUC.2015.10.020
Joerg H. Schrittwieser, Stefan Velikogne, Wolfgang Kroutil, Biocatalytic Imine Reduction and Reductive Amination of Ketones Advanced Synthesis & Catalysis. ,vol. 357, pp. 1655- 1685 ,(2015) , 10.1002/ADSC.201500213
Michael Fuchs, Judith E. Farnberger, Wolfgang Kroutil, The Industrial Age of Biocatalytic Transamination European Journal of Organic Chemistry. ,vol. 2015, pp. 6965- 6982 ,(2015) , 10.1002/EJOC.201500852
M. Shaheer Malik, Eul-Soo Park, Jong-Shik Shin, Features and technical applications of ω-transaminases. Applied Microbiology and Biotechnology. ,vol. 94, pp. 1163- 1171 ,(2012) , 10.1007/S00253-012-4103-3
Guangyue Li, Jie Ren, Peiyuan Yao, Yitao Duan, Hailing Zhang, Qiaqing Wu, Jinhui Feng, Peter C. K. Lau, Dunming Zhu, Deracemization of 2-Methyl-1,2,3,4-Tetrahydroquinoline Using Mutant Cyclohexylamine Oxidase Obtained by Iterative Saturation Mutagenesis ACS Catalysis. ,vol. 4, pp. 903- 908 ,(2014) , 10.1021/CS401065N
Eduardo Busto, Vicente Gotor-Fernández, Vicente Gotor, Chemoenzymatic synthesis of chiral 4-(N,N-dimethylamino)pyridine derivatives Tetrahedron-asymmetry. ,vol. 16, pp. 3427- 3435 ,(2005) , 10.1016/J.TETASY.2005.09.006
Barbara Kasprzyk-Hordern, Pharmacologically active compounds in the environment and their chirality Chemical Society Reviews. ,vol. 39, pp. 4466- 4503 ,(2010) , 10.1039/C000408C
C. K. Savile, J. M. Janey, E. C. Mundorff, J. C. Moore, S. Tam, W. R. Jarvis, J. C. Colbeck, A. Krebber, F. J. Fleitz, J. Brands, P. N. Devine, G. W. Huisman, G. J. Hughes, Biocatalytic Asymmetric Synthesis of Chiral Amines from Ketones Applied to Sitagliptin Manufacture Science. ,vol. 329, pp. 305- 309 ,(2010) , 10.1126/SCIENCE.1188934
Zhenming Zhang, Wanqing Wu, Jianhua Liao, Jianxiao Li, Huanfeng Jiang, Intermolecular asymmetric carboesterification of alkenes by using chiral amine auxiliaries under O2: synthesis of enantioenriched α-methylene-γ-lactones through chloropalladation of alkynes. Chemistry: A European Journal. ,vol. 21, pp. 6708- 6712 ,(2015) , 10.1002/CHEM.201500397