Carboxylic Acid Reductase Can Catalyze Ester Synthesis in Aqueous Environments

Most of the well‐known enzymes catalyzing esterification require the minimization of water or activated substrates for activity. This work reports a new reaction catalyzed by carboxylic acid reductase (CAR), an enzyme known to transform a broad spectrum of carboxylic acids into aldehydes, with the u...

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Bibliographic Details
Published in:Angewandte Chemie 2021-03, Vol.133 (11), p.5813-5817
Main Authors: Pongpamorn, Pornkanok, Kiattisewee, Cholpisit, Kittipanukul, Narongyot, Jaroensuk, Juthamas, Trisrivirat, Duangthip, Maenpuen, Somchart, Chaiyen, Pimchai
Format: Article
Language:English
Subjects:
Acyltransferase
Aldehydes
Aqueous environments
biocatalysts
carboxylic acid reductase
Carboxylic acids
Chemical synthesis
Chemistry
Enzymes
Esterification
green chemistry
Imidazole
imidazole buffer
Magnesium
Moisture content
Reductases
Room temperature
Substrates
Sun screens
Water content
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Summary:Most of the well‐known enzymes catalyzing esterification require the minimization of water or activated substrates for activity. This work reports a new reaction catalyzed by carboxylic acid reductase (CAR), an enzyme known to transform a broad spectrum of carboxylic acids into aldehydes, with the use of ATP, Mg2+, and NADPH as co‐substrates. When NADPH was replaced by a nucleophilic alcohol, CAR from Mycobacterium marinum can catalyze esterification under aqueous conditions at room temperature. Addition of imidazole, especially at pH 10.0, significantly enhanced ester production. In comparison to other esterification enzymes such as acyltransferase and lipase, CAR gave higher esterification yields in direct esterification under aqueous conditions. The scalability of CAR catalyzed esterification was demonstrated for the synthesis of cinoxate, an active ingredient in sunscreen. The CAR esterification offers a new method for green esterification under high water content conditions. An efficient and green method is presented for the synthesis of esters using carboxylic acid reductase as a biocatalyst under mild aqueous conditions.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.202013962