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Abstract
A key aim of biocatalysis is to mimic the ability of eukaryotic cells to carry out multistep cascades in a controlled and selective way. As biocatalytic cascades get more complex, reactions become unattainable under typical batch conditions. Here a number of continuous flow systems were used to overcome batch incompatibility, thus allowing for successful biocatalytic cascades. As proof‐of‐principle, reactive carbonyl intermediates were generated in situ using alcohol 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 via 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 4O‐methylnorbelladine.
Highlights
Multi-step synthesis in biocatalysis has been made more efficient through the utilization of enzymatic cascades
Another advantage is that continuous flow systems can be composed of different modules, which can enable the combination of a broad range of chemistries that are incompatible under batch conditions (Figure 1).[9]
As aldehydes are versatile yet unstable intermediates, it was thought a continuous flow system that generated this group in situ at high concentrations could allow for a range of subsequent enzymatic modifications
Summary
Multi-step synthesis in biocatalysis has been made more efficient through the utilization of enzymatic cascades. Flow chemistry has seen rapid development in recent years, with the potential to improve about 50 % of chemical processes.[6] Small scale flow systems can be translated into larger scale production with minimal optimization as the systems can be run for longer to increase productivity, a luxury not afforded in batch processes which need to be scaled up.[7,8] Another advantage is that continuous flow systems can be composed of different modules (different reactor types), which can enable the combination of a broad range of chemistries that are incompatible under batch conditions (Figure 1).[9] Further to this, the utilization of continuous flow systems facilitates the integration of several reaction steps resulting in telescoped synthetic sequences.[10]. Tabelle 1: Representation of the MPIR-packed bed continuous flow system for the biocatalytic synthesis of amines from alcohols.[a]
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