Studies on the Oxidation of Aromatic Amines Catalyzed by <i>Trametes versicolor</i> Laccase
The bio-oxidation of a series of aromatic amines catalyzed by <i>T. versicolor</i> laccase has been investigated exploiting either commercially available nitrogenous substrates [(<i>E</i>)-4-vinyl aniline and diphenyl amine] or ad hoc synthetized ones [(<i>E</i>)-...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2023-02-01
|
| Series: | International Journal of Molecular Sciences |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1422-0067/24/4/3524 |
| Summary: | The bio-oxidation of a series of aromatic amines catalyzed by <i>T. versicolor</i> laccase has been investigated exploiting either commercially available nitrogenous substrates [(<i>E</i>)-4-vinyl aniline and diphenyl amine] or ad hoc synthetized ones [(<i>E</i>)-4-styrylaniline, (<i>E</i>)-4-(prop-1-en-1-yl)aniline and (<i>E</i>)-4-(((4-methoxyphenyl)imino)methyl)phenol]. At variance to their phenolic equivalents, the investigated aromatic amines were not converted into the expected cyclic dimeric structures under <i>T. versicolor</i> catalysis. The formation of complex oligomeric/polymeric or decomposition by-products was mainly observed, with the exception of the isolation of two interesting but unexpected chemical skeletons. Specifically, the biooxidation of diphenylamine resulted in an oxygenated quinone-like product, while, to our surprise, in the presence of <i>T. versicolor</i> laccase (<i>E</i>)-4-vinyl aniline was converted into a 1,2-substited cyclobutane ring. To the best of our knowledge, this is the first example of an enzymatically triggered [2 + 2] olefin cycloaddition. Possible reaction mechanisms to explain the formation of these products are also reported. |
|---|---|
| ISSN: | 1661-6596 1422-0067 |