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A highly efficient one-enzyme protocol using ω-transaminase and an amino donor enabling equilibrium displacement assisted by molecular oxygen

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Abstract

We describe a highly efficient one-enzyme procedure using ω-transaminase in the absence of expensive cofactor (NAD(P)H)-dependent enzymes used for a by-product removal process. The aromatic amino donor benzylamine, enabling its acceptance by transaminases with either (R)- or (S)-enantioselectivity, was used, allowing reactions to proceed in excellent conversions using only 3 equivalents of the amino donor. During the transamination reaction, the generated co-product aldehyde was irreversibly converted to its corresponding carboxylic acid assisted by aerobic oxidation with 1 atmosphere of oxygen, therefore the equilibrium was successfully pushed to the product side. The aerobic oxidation promoted transamination, and the corresponding method was compatible with a wide spectrum of ω-transaminases. The amino donor used here is easily and commercially obtainable, and is suitable for low-cost and scalable preparations, representing a promising pathway for clean synthesis of high value-added chiral amines.

Graphical abstract: A highly efficient one-enzyme protocol using ω-transaminase and an amino donor enabling equilibrium displacement assisted by molecular oxygen

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Publication details

The article was received on 30 Jan 2018, accepted on 21 Mar 2018 and first published on 21 Mar 2018


Article type: Research Article
DOI: 10.1039/C8QO00100F
Citation: Org. Chem. Front., 2018, Advance Article
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    A highly efficient one-enzyme protocol using ω-transaminase and an amino donor enabling equilibrium displacement assisted by molecular oxygen

    Y. Cheng, Q. Shan, Y. Zhang, Z. Quan, K. Zhang and B. Wang, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO00100F

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