Data di Pubblicazione:
2023
Citazione:
Caulobacter segnis dioxygenase CsO2: a practical biocatalyst for stilbenoid ozonolysis / V. De Vitis, P. Cannazza, L. Mattio, D. Romano, A. Pinto, F. Molinari, T. Laurenzi, I. Eberini, M.L. Contente. - In: CHEMBIOCHEM. - ISSN 1439-4227. - (2023), pp. e202300477.1-e202300477.6. [Epub ahead of print] [10.1002/cbic.202300477]
Abstract:
Ozonolysis is a useful as well as dangerous reaction for performing alkene cleavage. On the other hand, enzymes are considered a more sustainable and safer alternative. Among them, Caulobacter segnis dioxygenase (CsO2) known so far for its ability to catalyze the coenzyme-free oxidation of vinylguaiacol into vanillin, was selected and its substrate scope evaluated towards diverse natural and synthetic stilbenoids. Under optimized conditions, CsO2 catalyzed the oxidative cleavage of the C=C double bonds of various trans-stilbenes, providing that a hydroxyl moiety was necessary in para-position of the phenyl group (e.g., resveratrol and its derivatives) for the reaction to take place, which was confirmed by modelling studies. The reactions occurred rapidly (0.5-3 h) with high conversions (95-99%) and without formation of by-products. The resveratrol biotransformation was carried out on 50-mL scale thus confirming the feasibility of the biocatalytic system as a preparative method.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
Alkene cleavage reaction; Caulobacter segnis dioxygenase; CsO2; Enzymatic ozonolysis-like reaction; Stilbenoids
Elenco autori:
V. De Vitis, P. Cannazza, L. Mattio, D. Romano, A. Pinto, F. Molinari, T. Laurenzi, I. Eberini, M.L. Contente
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