Biotechnology Letters, Vol.24, No.12, 979-983, 2002
Regioselective preparation of 2',3'-di-O-acylribonucleosides carrying lipophilic acyl groups through a lipase-catalysed alcoholysis
Candida antarctica B lipase-catalysed alcoholysis of 2', 3', 5'-tri-O-hexanoyluridine (1a), 2', 3', 5'-tri-O-dodecanoyluridine (1b), 2', 3', 5'-tri-O-hexanoylinosine (1c) and 2', 3', 5'-tri-O-dodecanoylinosine (1d) proceeded regioselectively to produce the corresponding 2', 3'-di-O-acylribonucleosides 2a-d, providing a simple and efficient access to these new lipophilic compounds. Contrasting to the alcoholysis, enzymatic hydrolysis of 1a-d using different enzymes and experimental conditions did not proceed regioselectively.