Selective Electroenzymatic Oxyfunctionalization by Alkane Monooxygenase in a Biofuel Cell

Abstract

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 H2 as a clean fuel source, we have developed and characterized a series of enzymatic fuel cells capable of oxyfunctionalization while simultaneously producing electricity.

Document Details

Document Type
Pub Defense Publication
Publication Date
Apr 06, 2020
Source ID
10.1002/anie.202003032

Entities

People

  • Christian A. Malapit
  • Chun You
  • Hui Chen
  • Matthew J. Kummer
  • Mengwei Yuan
  • Shelley D. Minteer
  • Sofiène Abdellaoui

Organizations

  • National Science Foundation
  • Tianjin Institute of Industrial Biotechnology
  • University of Reims
  • University of Utah

Tags

Fields of Study

  • Chemistry

Readers

  • Microbial Pathology
  • Molecular and Cellular Biochemistry
  • Organic Chemistry

Technology Areas

  • Biotechnology