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.

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. - 24:21(2023 Nov 02), pp. e202300477.1-e202300477.6. [10.1002/cbic.202300477]

Caulobacter segnis dioxygenase CsO2: a practical biocatalyst for stilbenoid ozonolysis

V. De Vitis
Primo
;
P. Cannazza
Secondo
;
L. Mattio;D. Romano;A. Pinto;F. Molinari;T. Laurenzi;I. Eberini
Penultimo
;
M.L. Contente
Ultimo
2023

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.
Alkene cleavage reaction; Caulobacter segnis dioxygenase; CsO2; Enzymatic ozonolysis-like reaction; Stilbenoids
Settore CHIM/11 - Chimica e Biotecnologia delle Fermentazioni
Settore CHIM/10 - Chimica degli Alimenti
Settore CHIM/06 - Chimica Organica
Settore BIO/10 - Biochimica
   Metal-containing Radical Enzymes (MetRaZymes)
   MetRaZymes
   EUROPEAN COMMISSION
   101073546

   PIANO DI SOSTEGNO ALLA RICERCA 2015-2017 - TRANSITION GRANT LINEA 1A PROGETTO "UNIMI PARTENARIATI H2020"

   Citrus waste recycling for added value products (CIRCLE)
   CIRCLE
   FONDAZIONE CARIPLO
   2020-1070
2-nov-2023
15-lug-2023
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/997668
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