386263-87-2Relevant articles and documents
Enantioselective CO2 Fixation Via a Heck-Coupling/Carboxylation Cascade Catalyzed by Nickel
Cerveri, Alessandro,Giovanelli, Riccardo,Sella, Davide,Pedrazzani, Riccardo,Monari, Magda,Nieto Faza, Olalla,López, Carlos Silva,Bandini, Marco
supporting information, p. 7657 - 7662 (2021/05/03)
A novel asymmetric nickel-based procedure has been developed in which CO2 fixation is achieved as a second step of a truncated Heck coupling. For this, a new chiral ligand has been prepared and shown to achieve enantiomeric excesses up to 99 %. The overall process efficiently furnishes chiral 2,3-dihydrobenzofuran-3-ylacetic acids, an important class of bioactive products, from easy to prepare starting materials. A combined experimental and computational effort revealed the key steps of the catalytic cycle and suggested the unexpected participation of Ni(I) species in the coupling event.
Cutinase from Fusarium oxysporum catalyzes the acylation of tyrosol in an aqueous medium: Optimization and thermodynamic study of the reaction
Nikolaivits, Efstratios,Norra, Giannis-Florjan,Voutsas, Epaminondas,Topakas, Evangelos
, p. 29 - 36 (2016/04/20)
Recently, tyrosol has gained attention as a result of its many pharmacological properties and due to the fact that it can be isolated from cheap and abundant resources. Lipophilic tyrosyl esters, which are scarce in nature, have proven in certain cases to acquire improved biological activity compared to tyrosol itself, increasing their potential use in the food and cosmeceutical industries. The enzymatic approach for the synthesis of such esters has prevailed, as it is "green", compared to chemical practices. We hereby report the enzymatic synthesis of tyrosyl esters of various aliphatic fatty acids performed by a recombinant cutinase from Fusarium oxysporum (FoCut5a). The reaction system used consists of an aqueous phase saturated with the corresponding fatty-acid vinyl ester, which played the role of the acyl donor. We also proceeded to the study of several parameters on the yield of the tyrosyl butyrate ester synthesis. The maximum yield achieved was 60.7% after 4 h at 20 °C, in pH 7.0, with initial tyrosol concentration of 12.5 mM and using 5 μg FoCut5a mL-1 reaction as catalyst. The optimum reaction conditions can be considered mild, highlighting the environmentally friendly nature of this reaction, along with the fact that there are not any harmful reagents involved. Additionally, the use of two thermodynamic models, Conductor-like Screening Model for Real Solvents (COSMO-RS) and UNIquac Functional-group Activity Coefficients (UNIFAC), were employed for the prediction of reactants' and products' solubilities and their distribution in the reaction biphasic system, aiming to correlate the reaction yields with these important thermodynamic quantities and understand the ability of this enzymatic reaction in synthesizing tyrosyl esters.
Tyrosinase and Layer-by-Layer supported tyrosinases in the synthesis of lipophilic catechols with antiinfluenza activity
Bozzini, Tiziana,Botta, Giorgia,Delfino, Michela,Onofri, Silvano,Saladino, Raffaele,Amatore, Donatella,Sgarbanti, Rossella,Nencioni, Lucia,Palamara, Anna Teresa
, p. 7699 - 7708 (2014/01/06)
Catechol derivatives with lipophilic properties have been selectively synthesized by tyrosinase in high yield avoiding long and tedious protection/deprotection steps usually required in traditional procedures. The synthesis was effective also with immobilized tyrosinase able to perform for more runs. The novel catechols were evaluated against influenza A virus, that continue to represent a severe threat worldwide. A significant antiviral activity was observed in derivatives characterized by antioxidant activity and long carbon alkyl side-chains, suggesting the possibility of a new inhibition mechanism based on both redox and lipophilic properties.
