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Lipase-catalyzed regioselective acylation of resorcin[4]arenes

2002; Elsevier BV; Volume: 16; Issue: 5-6 Linguagem: Inglês

10.1016/s1381-1177(01)00068-6

1873-3158

Bruno Botta, Giovanni Zappia, Andrea Tafi, Maurizio Botta, Fabrizio Manetti, E. Cernia, Giuliana Milana, Cleofe Palocci, Simonetta Soro, Giuliano Delle Monache,

Mass Spectrometry Techniques and Applications

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.