Reductive amination of ketones with ammonium catalyzed by a newly identified Brevibacterium epidermidis strain for the synthesis of (S)-chiral amines

doi:10.1016/S1872-2067(18)63108-0

Abstract

Abstract:

The asymmetric reductive amination of achiral ketones with ammonia is a particularly attractive reaction for the synthesis of chiral amines. Although several engineered amine dehydrogenases have been developed by protein engineering for the asymmetric reductive amination of ketones, they all display (R)-stereoselectivity. To date, there is no report of an (S)-stereoselective biocatalyst for this reaction. Herein, a microorganism named Brevibacterium epidermidis ECU1015 that catalyzes the (S)-selective reductive amination of ketones with ammonium has been successfully isolated from soil. Using B. epidermidis ECU1015 as the catalyst, the asymmetric reductive amination of a set of phenylacetone derivatives was successfully carried out, yielding the corresponding (S)-chiral amines with moderate conversion and >99% enantiomeric excess.

Key words: Biocatalysis, Reductive amination, Asymmetric synthesis, Prochiral ketones, Chiral amine

Qing-Hua Li, Yuan Dong, Fei-Fei Chen, Lei Liu, Chun-Xiu Li, Jian-He Xu, Gao-Wei Zheng. Reductive amination of ketones with ammonium catalyzed by a newly identified Brevibacterium epidermidis strain for the synthesis of (S)-chiral amines[J]. Chinese Journal of Catalysis, 2018, 39(10): 1625-1632.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(18)63108-0

https://www.cjcatal.com/EN/Y2018/V39/I10/1625

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