Food-derived phenolic compounds are well known for their antioxidant and antimicrobial effects1. Because of their hydrophilic nature and their intrinsic stability and bioavailability issues, their use as active ingredients is limited. Lipophilization of phenolic derivatives is a valid strategy to obtain amphiphilic compounds that can be used as multifunctional additives in the pharmaceutical, nutraceutical, and cosmetic fields2. In particular, the synthesis of carbonates and carbamates is an attractive strategy to increase the lipophilicity of phenolic derivatives. However, their classic synthesis requires the employment of toxic acylating agents, unsafe solvents and experimental conditions. In this context, we developed a reproducible, green, and scalable chemo-enzymatic flow process for the obtainment of a series of lipophilic carbonate and carbamate derivatives (Scheme 1) of natural tyrosol (Ty) and hydroxytyrosol (HTy)3,4. Immobilized CaLB was used in a packed bed reactor for the selective carbonation of the primary alcohol of Ty and HTy in a non-conventional green solvent as tert-amyl alcohol. Then, two selected carbonates were reacted in flow with the appropriate amine to obtain the desired carbamates. A telescoped two-step process was set up allowing to reduce the manual handling, time, and costs of the process. All compounds were tested as antimicrobials and radical scavengers and they showed similar or even better activity compared to the parent compound, with a significant increase in their lipophilicity.
Chemo-enzymatic flow synthesis of nature-inspired phenolic carbonates and carbamates as antimicrobial and antiradical agents / F. Annunziata, S. Vicinanza, L. Mombelli, S. Donzella, G. Meroni, C. Borsari, M.L. Contente, P.A. Martino, P. Conti, A. Pinto, S. Dallavalle, L. Tamborini. ((Intervento presentato al 28. convegno National Congress SCI : Chemistry Elements of Future : 26-30 august tenutosi a Milano nel 2024.
Chemo-enzymatic flow synthesis of nature-inspired phenolic carbonates and carbamates as antimicrobial and antiradical agents
F. Annunziata;S. Vicinanza;L. Mombelli;S. Donzella;G. Meroni;C. Borsari;M.L. Contente;P.A. Martino;P. Conti;A. Pinto;S. Dallavalle;L. Tamborini
2024
Abstract
Food-derived phenolic compounds are well known for their antioxidant and antimicrobial effects1. Because of their hydrophilic nature and their intrinsic stability and bioavailability issues, their use as active ingredients is limited. Lipophilization of phenolic derivatives is a valid strategy to obtain amphiphilic compounds that can be used as multifunctional additives in the pharmaceutical, nutraceutical, and cosmetic fields2. In particular, the synthesis of carbonates and carbamates is an attractive strategy to increase the lipophilicity of phenolic derivatives. However, their classic synthesis requires the employment of toxic acylating agents, unsafe solvents and experimental conditions. In this context, we developed a reproducible, green, and scalable chemo-enzymatic flow process for the obtainment of a series of lipophilic carbonate and carbamate derivatives (Scheme 1) of natural tyrosol (Ty) and hydroxytyrosol (HTy)3,4. Immobilized CaLB was used in a packed bed reactor for the selective carbonation of the primary alcohol of Ty and HTy in a non-conventional green solvent as tert-amyl alcohol. Then, two selected carbonates were reacted in flow with the appropriate amine to obtain the desired carbamates. A telescoped two-step process was set up allowing to reduce the manual handling, time, and costs of the process. All compounds were tested as antimicrobials and radical scavengers and they showed similar or even better activity compared to the parent compound, with a significant increase in their lipophilicity.File | Dimensione | Formato | |
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