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Bi‐enzymatic Conversion of Cinnamic Acids to 2‐Arylethylamines
Author(s) -
Weise Nicholas J.,
Thapa Prasansa,
Ahmed Syed T.,
Heath Rachel S.,
Parmeggiani Fabio,
Turner Nicholas J.,
Flitsch Sabine L.
Publication year - 2020
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201902128
Subject(s) - biotransformation , chemistry , cinnamic acid , enzyme , amino acid , organic chemistry , biocatalysis , tandem , carboxylic acid , combinatorial chemistry , ring (chemistry) , organic synthesis , transformation (genetics) , biochemistry , reaction mechanism , catalysis , materials science , composite material , gene
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.