Regioselective preparation of 2′, 3′-di-O-acylribonucleosides carrying lipophilic acyl groups through a lipase-catalysed alcoholysis

• Main Authors: Zinni, M.A., Iglesias, L.E., Iribarren, A.M.
• Format: Journal/Newspaper
• Language: unknown
• Subjects: 2′; 3′-di-O-acylribonucleosides; Deacylation; Enzymatic alcoholysis; Lipases; Nucleosides; 2',3' di o acylribonucleoside; 2',3' di o dodecanoylinosine; 2',3' di o dodecanoyluridine; 2',3' di o hexanoylinosine; 2',3' di o hexanoyluridine; 2',3',5' tri o dodecanoylinosine; 2',3',5' tri o dodecanoyluridine; 2',3',5' tri o hexanoylinosine; 2',3',5' tri o hexanoyluridine; antivirus agent; inosine derivative; nucleoside analog; ribonucleoside derivative; unclassified drug; uridine derivative; acylation; antiviral activity; article; catalysis; chemical structure; controlled study; enzyme activity; high performance liquid chromatography; hydrolysis; lipophilicity; nonhuman; thin layer chromatography; Candida; Candida antarctica; Antarc*; Antarctica
• Online Access: https://hdl.handle.net/20.500.12110/paper_01415492_v24_n12_p979_Zinni

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.