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Molecules 2017, 22(12), 2205; https://doi.org/10.3390/molecules22122205

Rational Engineering of a Flavoprotein Oxidase for Improved Direct Oxidation of Alcohols to Carboxylic Acids

1
Department of Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria
2
Austrian Centre of Industrial Biotechnology, ACIB GmbH c/o Department of Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria
3
Molecular Enzymology Group, Groningen Biomolecular Sciences and Biotechnology Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands
*
Author to whom correspondence should be addressed.
Received: 21 November 2017 / Revised: 6 December 2017 / Accepted: 8 December 2017 / Published: 12 December 2017
(This article belongs to the Special Issue Flavoenzymes)
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Abstract

The oxidation of alcohols to the corresponding carbonyl or carboxyl compounds represents a convenient strategy for the selective introduction of electrophilic carbon centres into carbohydrate-based starting materials. The O2-dependent oxidation of prim-alcohols by flavin-containing alcohol oxidases often yields mixtures of aldehyde and carboxylic acid, which is due to “over-oxidation” of the aldehyde hydrate intermediate. In order to directly convert alcohols into carboxylic acids, rational engineering of 5-(hydroxymethyl)furfural oxidase was performed. In an attempt to improve the binding of the aldehyde hydrate in the active site to boost aldehyde-oxidase activity, two active-site residues were exchanged for hydrogen-bond-donating and -accepting amino acids. Enhanced over-oxidation was demonstrated and Michaelis–Menten kinetics were performed to corroborate these findings. View Full-Text
Keywords: biocatalysis; alcohol oxidation; aldehyde oxidation; flavoprotein oxidase; protein design biocatalysis; alcohol oxidation; aldehyde oxidation; flavoprotein oxidase; protein design
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Pickl, M.; Winkler, C.K.; Glueck, S.M.; Fraaije, M.W.; Faber, K. Rational Engineering of a Flavoprotein Oxidase for Improved Direct Oxidation of Alcohols to Carboxylic Acids. Molecules 2017, 22, 2205.

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