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Selective Electroenzymatic Oxyfunctionalization by Alkane Monooxygenase in a Biofuel Cell
Author(s) -
Yuan Mengwei,
Abdellaoui Sofiene,
Chen Hui,
Kummer Matthew J.,
Malapit Christian A.,
You Chun,
Minteer Shelley D.
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202003032
Subject(s) - alkb , alkane , chemistry , monooxygenase , hydroxylation , pseudomonas putida , organic chemistry , methane monooxygenase , combinatorial chemistry , catalysis , enzyme , biochemistry , cytochrome p450 , dna repair , gene
Aliphatic synthetic intermediates with high added value are generally produced from alkane sources (e.g., petroleum) by inert carbon–hydrogen (C−H) bond activation using classical chemical methods (i.e. high temperature, rare metals). As an alternative approach for these reactions, alkane monooxygenase from Pseudomonas putida (alkB) is able to catalyze the difficult terminal oxyfunctionalization of alkanes selectively and under mild conditions. Herein, we report an electrosynthetic system using an alkB biocathode which produces alcohols, epoxides, and sulfoxides through bioelectrochemical hydroxylation, epoxidation, sulfoxidation, and demethylation. The capacity of the alkB binding pocket to protect internal functional groups is also demonstrated. By coupling our alkB biocathode with a hydrogenase bioanode and using H 2 as a clean fuel source, we have developed and characterized a series of enzymatic fuel cells capable of oxyfunctionalization while simultaneously producing electricity.