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Rational Engineering of a Flavoprotein Oxidase for Improved Direct Oxidation of Alcohols to Carboxylic Acids
Open accessAbstract
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.
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Cited by
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Gan, B. H., Gaynord, J., Rowe, S. M., Deingruber, T., & Spring, D. R. (2021) · Chemical Society Reviews · doi:10.1039/d0cs00729c · Cited by 511
Badmus, S. O., Amusa, H. K., Oyehan, T. A., & Saleh, T. A. (2021) · Environmental Science and Pollution Research · doi:10.1007/s11356-021-16483-w · Cited by 459
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Metadata
- Authors
- Pickl, M., Winkler, C., Glueck, S., Fraaije, M., & Faber, K.
- Venue
- Molecules
- Publisher
- MDPI AG
- Published
- 2017-12-12
- Volume
- 22
- Issue
- 12
- Pages
- 2205
- ISSN
- 1420-3049 (ISSN-L)
- OpenAlex
- W2773553108
- Cited by
- 274
- References
- 0
- FWCI
- 16.69
- Type
- journal article
- Language
- en
- Open access
- gold
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- Pickl, M., Winkler, C., Glueck, S., Fraaije, M., & Faber, K. (2017). Rational Engineering of a Flavoprotein Oxidase for Improved Direct Oxidation of Alcohols to Carboxylic Acids. Molecules. https://doi.org/10.3390/molecules22122205
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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