Data di Pubblicazione:
2023
Citazione:
Studies on the Oxidation of Aromatic Amines Catalyzed by Trametes versicolor Laccase / I. Bassanini, S. Grosso, C. Tognoli, G. Fronza, S. Riva. - In: INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES. - ISSN 1422-0067. - 24:4(2023 Feb 09), pp. 3524.1-3524.12. [10.3390/ijms24043524]
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.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
biocatalyzed [2 + 2] olefin cycloaddition; T. versicolor laccases; anilines; bio-oxidation; radical chemistry
Elenco autori:
I. Bassanini, S. Grosso, C. Tognoli, G. Fronza, S. Riva
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