NDLI: Studies on the Oxidation of Aromatic Amines Catalyzed by <i>Trametes versicolor</i> Laccase.

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Studies on the Oxidation of Aromatic Amines Catalyzed by Trametes versicolor Laccase.

Content Provider	Europe PMC
Author	Bassanini, Ivan Grosso, Simone Tognoli, Chiara Fronza, Giovanni Riva, Sergio
Editor	Pogni, Rebecca Baratto, Maria Camilla
Copyright Year	2023
Abstract	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.
Journal	International Journal of Molecular Sciences [Int J Mol Sci]
Volume Number	24
DOI	10.3390/ijms24043524
PubMed Central reference number	PMC9963649
Issue Number	4
PubMed reference number	36834934
e-ISSN	14220067
Language	English
Publisher	Molecular Diversity Preservation International (MDPI)
Publisher Date	2023-02-09
Access Restriction	Open
Subject Keyword	biocatalyzed [2 + 2] olefin cycloaddition T. versicolor laccases anilines bio-oxidation radical chemistry
Content Type	Text
Resource Type	Article
Subject	Physical and Theoretical Chemistry Molecular Biology Spectroscopy Catalysis Computer Science Applications Medicine Inorganic Chemistry Organic Chemistry

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