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Combined chemoenzymatic strategy for sustainable continuous synthesis of the natural product hordenine†
Stefania Gianolio,David Roura Padrosa,Francesca Paradisi
Green Chemistry Pub Date : 10/12/2022 00:00:00 , DOI:10.1039/D2GC02767D
Abstract

To improve sustainability, safety and cost-efficiency of synthetic methodologies, biocatalysis can be a helpful ally. In this work, a novel chemoenzymatic stategy ensures the rapid synthesis of hordenine, a valuable phenolic phytochemical under mild working conditions. In a two-step cascade, the immobilized tyrosine decarboxylase from Lactobacillus brevis (LbTDC) is here coupled with the chemical reductive amination of tyramine. Starting from the abundant and cost-effective amino acid L-tyrosine, the complete conversion to hordenine is achieved in less than 5 minutes residence time in a fully-automated continuous flow system. Compared to the metal-catalyzed N,N-dimethylation of tyramine, this biocatalytic approach reduces the process environmental impact and improves its STY to 2.68 g L−1 h−1.

Graphical abstract: Combined chemoenzymatic strategy for sustainable continuous synthesis of the natural product hordenine
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