Direct reductive amination of ketones with amines by reductive aminases

Direct reductive amination of ketones by reductive aminases (RedAms) is a promising method for the synthesis of primary, secondary and tertiary amines. In this work, five naturally occurring RedAms possessing reductive amination activity were identified using a structure-guided genome mining (SGGM)...

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Autores principales:	Bo-Bo Li, Jing Zhang, Fei-Fei Chen, Qi Chen, Jian-He Xu, Gao-Wei Zheng
Formato:	article
Lenguaje:	EN
Publicado:	KeAi Communications Co. Ltd. 2021
Materias:	Biocatalysis Reductive amination Reductive aminases Protein engineering Chiral amines Chemical technology TP1-1185 Biochemistry QD415-436
Acceso en línea:	https://doaj.org/article/bcbca17f03544cf0868c9195bde2c22d
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spelling	oai:doaj.org-article:bcbca17f03544cf0868c9195bde2c22d2021-12-02T05:03:57ZDirect reductive amination of ketones with amines by reductive aminases2666-554910.1016/j.gresc.2021.08.005https://doaj.org/article/bcbca17f03544cf0868c9195bde2c22d2021-11-01T00:00:00Zhttp://www.sciencedirect.com/science/article/pii/S2666554921000776https://doaj.org/toc/2666-5549Direct reductive amination of ketones by reductive aminases (RedAms) is a promising method for the synthesis of primary, secondary and tertiary amines. In this work, five naturally occurring RedAms possessing reductive amination activity were identified using a structure-guided genome mining (SGGM) approach, which was based on highly conserved substrate binding and catalysis motif alignment. This RedAm toolbox facilitated the reductive amination of cyclohexanone and 4-fluoropropiophenone with various amine nucleophiles. In a preparative biotransformation (100 mg) with low stoichiometric ammonia donor and low catalyst loading, and three types of N-alkylcyclohexylamine were efficiently synthesized with a space-time yield up to 64.2 g L−1 d−1, demonstrating the potential of the RedAm enzymes as a biocatalyst toolbox for the synthesis of primary and secondary amines. Additionally, through protein engineering, the W205F variant of KfRedAm from Kribbella flavida was obtained with a 2-fold increased catalytic efficiency (kcat/Km), and the general applicability of the variant was verified, providing useful guidance for further evolution of RedAms within this family.Bo-Bo LiJing ZhangFei-Fei ChenQi ChenJian-He XuGao-Wei ZhengKeAi Communications Co. Ltd.articleBiocatalysisReductive aminationReductive aminasesProtein engineeringChiral aminesChemical technologyTP1-1185BiochemistryQD415-436ENGreen Synthesis and Catalysis, Vol 2, Iss 4, Pp 345-349 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	Biocatalysis Reductive amination Reductive aminases Protein engineering Chiral amines Chemical technology TP1-1185 Biochemistry QD415-436
spellingShingle	Biocatalysis Reductive amination Reductive aminases Protein engineering Chiral amines Chemical technology TP1-1185 Biochemistry QD415-436 Bo-Bo Li Jing Zhang Fei-Fei Chen Qi Chen Jian-He Xu Gao-Wei Zheng Direct reductive amination of ketones with amines by reductive aminases
description	Direct reductive amination of ketones by reductive aminases (RedAms) is a promising method for the synthesis of primary, secondary and tertiary amines. In this work, five naturally occurring RedAms possessing reductive amination activity were identified using a structure-guided genome mining (SGGM) approach, which was based on highly conserved substrate binding and catalysis motif alignment. This RedAm toolbox facilitated the reductive amination of cyclohexanone and 4-fluoropropiophenone with various amine nucleophiles. In a preparative biotransformation (100 mg) with low stoichiometric ammonia donor and low catalyst loading, and three types of N-alkylcyclohexylamine were efficiently synthesized with a space-time yield up to 64.2 g L−1 d−1, demonstrating the potential of the RedAm enzymes as a biocatalyst toolbox for the synthesis of primary and secondary amines. Additionally, through protein engineering, the W205F variant of KfRedAm from Kribbella flavida was obtained with a 2-fold increased catalytic efficiency (kcat/Km), and the general applicability of the variant was verified, providing useful guidance for further evolution of RedAms within this family.
format	article
author	Bo-Bo Li Jing Zhang Fei-Fei Chen Qi Chen Jian-He Xu Gao-Wei Zheng
author_facet	Bo-Bo Li Jing Zhang Fei-Fei Chen Qi Chen Jian-He Xu Gao-Wei Zheng
author_sort	Bo-Bo Li
title	Direct reductive amination of ketones with amines by reductive aminases
title_short	Direct reductive amination of ketones with amines by reductive aminases
title_full	Direct reductive amination of ketones with amines by reductive aminases
title_fullStr	Direct reductive amination of ketones with amines by reductive aminases
title_full_unstemmed	Direct reductive amination of ketones with amines by reductive aminases
title_sort	direct reductive amination of ketones with amines by reductive aminases
publisher	KeAi Communications Co. Ltd.
publishDate	2021
url	https://doaj.org/article/bcbca17f03544cf0868c9195bde2c22d
work_keys_str_mv	AT boboli directreductiveaminationofketoneswithaminesbyreductiveaminases AT jingzhang directreductiveaminationofketoneswithaminesbyreductiveaminases AT feifeichen directreductiveaminationofketoneswithaminesbyreductiveaminases AT qichen directreductiveaminationofketoneswithaminesbyreductiveaminases AT jianhexu directreductiveaminationofketoneswithaminesbyreductiveaminases AT gaoweizheng directreductiveaminationofketoneswithaminesbyreductiveaminases
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Direct reductive amination of ketones with amines by reductive aminases

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