Mattey, AP, ford, G, Citoler, J, Baldwin, C, Marshall, J, Pamer, R, thompson, MP, Turner, N, Cosgrove, SC ORCID: https://orcid.org/0000-0001-9541-7201 and Flitsch, S (2021) Production of High Value Amine Intermediates via Biocatalytic Cascades in Continuous Flow. Organic Chemistry. (Unpublished)

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Abstract

<jats:p>A key aim of biocatalysis is to mimic the ability of eukaryotic cells to carry out compartmentalized multistep cascades in a controlled and selective way. As biocatalytic cascades get longer and more complex, reactions become unattainable under typical batch conditions. Here a continuous flow multipoint injection reactor was combined with switching valves to overcome batch incompatibility, thus allowing for successful biocatalytic reaction cascades. As proof-of-principle, several reactive carbonyl intermediates were generated <jats:italic>in situ </jats:italic>using galactose oxidase and engineered choline oxidases, then passed directly to a series of packed-bed modules containing different aminating biocatalysts which accordingly produced a range of structurally distinct amines. The method was expanded to employ a batch incompatible sequential amination cascade <jats:italic>via </jats:italic>an oxidase-transaminase-imine reductase sequence, introducing different amine reagents at each step without cross reactivity. The combined approaches allowed for the biocatalytic synthesis of the natural product alkaloid precursor 4O-methylnorbelladine. The flow biocatalysis platform shown here significantly increases the scope of novel biocatalytic cascades, removing previous limitations due to reaction and reagent batch incompatibility.</jats:p>

Item Type: Article
Additional Information: The final version of this article and all relevant information related to it can be found on the publisher website.
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Divisions: Faculty of Natural Sciences > School of Chemical and Physical Sciences
Depositing User: Symplectic
Date Deposited: 02 Nov 2021 16:38
Last Modified: 02 Nov 2021 16:38
URI: https://eprints.keele.ac.uk/id/eprint/10205

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