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Lipase-catalyzed regioselective acylation of resorcin[4]arenes |
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| Authors: | Bruno Botta Giovanni Zappia Andrea Tafi Maurizio Botta Fabrizio Manetti Enrico Cernia Giuliana Milana Cleofe Palocci Simonetta Soro Giuliano Delle Monache |
| Affiliation: | a Dipartimento di Studi di Chimica e Tecnologia delle Sostanze Biologicamente Attive, Università La Sapienza, P. le A. Moro 5, I-00185 Rome, Italy b Dipartimento Farmaco Chimico Tecnologico, Università degli Studi di Siena, Via A. Moro snc, I-53100 Siena, Italy c Dipartimento di Chimica (NEC), Università La Sapienza, P. le A. Moro 5, I-00185 Rome, Italy d Centro Chimica dei Recettori, Università Cattolica del S. Cuore, Largo F. Vito 1, I-00168 Rome, Italy |
| Abstract: | Immobilized lipase from Mucor miehei (RML) catalyzed the regioselective acylation of the C-2 side-chain of the C-alkyl resorcin[4]arene tetra-alcohol 1 in the 1,2-alternate form in organic solvents using vinyl acetate as acylating reagent. The influence of reaction parameters and solvent choice were also studied. Docking simulations allowed the determination of the binding geometry of 1, revealing the importance of Trp88 residue in stabilizing the Michaelis–Menten complex between enzyme and substrate. |
| Keywords: | Resorcinarene Lipase Transesterification Molecular modeling Docking |
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