Biocatalyzed flow oxidation of tyrosol to hydroxytyrosol and efficient production of their acetate esters
Articolo
Data di Pubblicazione:
2021
Citazione:
Biocatalyzed flow oxidation of tyrosol to hydroxytyrosol and efficient production of their acetate esters / F. Annunziata, M.L. Contente, C. Pinna, L. Tamborini, A. Pinto. - In: ANTIOXIDANTS. - ISSN 2076-3921. - 10:7(2021 Jul), pp. 1142.1-1142.8. [10.3390/antiox10071142]
Abstract:
Tyrosol (Ty) and hydroxytyrosol (HTy) are valuable dietary phenolic compounds present in olive oil and wine, widely used for food, nutraceutical and cosmetic applications. Ty and HTy are endowed with a number of health-related biological activities, including antioxidant, antimicrobial and anti-inflammatory properties. In this work, we developed a sustainable, biocatalyzed flow protocol for the chemo-and regio-selective oxidation of Ty into HTy catalyzed by free tyrosinase from Agaricus bisporus in a gas/liquid biphasic system. The aqueous flow stream was then in-line extracted to recirculate the water medium containing the biocatalyst and the excess ascorbic acid, thus improving the cost-efficiency of the process and creating a self-sufficient closed-loop system. The organic layer was purified in-line through a catch-and-release procedure using supported boronic acid that was able to trap HTy and leave the unreacted Ty in solution. Moreover, the acetate derivatives (TyAc and HTyAc) were produced by exploiting a bioreactor packed with an immobilized acyltransferase from Mycobacterium smegmatis (MsAcT), able to selectively act on the primary alcohol. Under optimized conditions, high-value HTy was obtained in 75% yield, whereas TyAc and HTyAc were isolated in yields of up to 80% in only 10 min of residence time.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
Acetate derivatives; Biocatalysis; Flow chemistry; Hydroxytyrosol; Oxidation; tyrosol
Elenco autori:
F. Annunziata, M.L. Contente, C. Pinna, L. Tamborini, A. Pinto
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