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

Gianolio, Stefania; Roura Padrosa, David; Paradisi, Francesca (2022). Combined chemoenzymatic strategy for sustainable continuous synthesis of the natural product hordenine. Green chemistry, 24(21), pp. 8434-8440. Royal Society of Chemistry 10.1039/D2GC02767D

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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·h).

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