Bi‐enzymatic Conversion of Cinnamic Acids to 2‐Arylethylamines. Issue 4 (2nd January 2020)

• Record Type: Journal Article
• Authors: Weise, Nicholas J.; Thapa, Prasansa; Ahmed, Syed T.; Heath, Rachel S.; Parmeggiani, Fabio; Turner, Nicholas J.; Flitsch, Sabine L.
• Is Part Of: ChemCatChem. Volume 12:Issue 4(2020)
• Page Start: 995
• Page End: 998
• Publication Date: 2020-01-02
• Subjects: arylethylamines -- biocatalysis -- enzyme cascades -- ammonia lyases -- decarboxylases; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201902128
• Languages: English
• ISSNs: 1867-3880

Abstract

Abstract: The conversion of carboxylic acids, such as acrylic acids, to amines is a transformation that remains challenging in synthetic organic chemistry. Despite the ubiquity of similar moieties in natural metabolic pathways, biocatalytic routes seem to have been overlooked for this purpose. Herein we present the conception and optimisation of a two‐enzyme system, allowing the synthesis of β‐phenylethylamine derivatives from readily‐available ring‐substituted cinnamic acids. After characterisation of both parts of the reaction in a two‐step approach, a set of conditions allowing the one‐pot biotransformation was optimised. This combination of a reversible deaminating and irreversible decarboxylating enzyme, both specific for the amino acid intermediate in tandem, represents a general method by which new strategies for the conversion of carboxylic acids to amines could be designed. Abstract : Biocatalysis : A combination of phenylalanine ammonia lyase and decarboxylase enzymes allows the conversion of aromatic acrylic acids to the corresponding ethylamines. The reaction can be performed either as a tandem reaction with facile work up in between or as a biocatalytic cascade in a common reaction medium. A variety of ring‐substituted cinnamic acid derivatives can serve as starting materials with varying conversion.