Studies on the Oxidation of Aromatic Amines Catalyzed by Trametes versicolor Laccase
| Autor: | Ivan Bassanini, Simone Grosso, Chiara Tognoli, Giovanni Fronza, Sergio Riva |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2023 |
| Předmět: |
biocatalyzed [2 + 2] olefin cycloaddition
T. versicolor laccases anilines bio-oxidation radical chemistry Organic Chemistry General Medicine Settore CHIM/08 - Chimica Farmaceutica Catalysis Computer Science Applications Inorganic Chemistry Physical and Theoretical Chemistry Molecular Biology Spectroscopy |
| Zdroj: | International Journal of Molecular Sciences Volume 24 Issue 4 Pages: 3524 |
| Popis: | The bio-oxidation of a series of aromatic amines catalyzed by T. versicolor laccase has been investigated exploiting either commercially available nitrogenous substrates [(E)-4-vinyl aniline and diphenyl amine] or ad hoc synthetized ones [(E)-4-styrylaniline, (E)-4-(prop-1-en-1-yl)aniline and (E)-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 T. versicolor 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 T. versicolor laccase (E)-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. |
| Databáze: | OpenAIRE |
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