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Abstract:

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.

Registro:

Documento: Artículo
Título:Regioselective preparation of 2′, 3′-di-O-acylribonucleosides carrying lipophilic acyl groups through a lipase-catalysed alcoholysis
Autor:Zinni, M.A.; Iglesias, L.E.; Iribarren, A.M.
Filiación:Centro de Estudios e Investigaciones, Universidad Nacional de Quilmes, Roque Sáenz Peña 180, (1876) Bernal, Prov. de Buenos Aires, Argentina
INGEBI (CONICET), Vuelta de Obligado 2490, (1428) Buenos Aires, Argentina
Palabras clave: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
Año:2002
Volumen:24
Número:12
Página de inicio:979
Página de fin:983
DOI: http://dx.doi.org/10.1023/A:1015648508146
Título revista:Biotechnology Letters
Título revista abreviado:Biotechnol. Lett.
ISSN:01415492
CODEN:BILED
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01415492_v24_n12_p979_Zinni

Referencias:

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Citas:

---------- APA ----------
Zinni, M.A., Iglesias, L.E. & Iribarren, A.M. (2002) . Regioselective preparation of 2′, 3′-di-O-acylribonucleosides carrying lipophilic acyl groups through a lipase-catalysed alcoholysis. Biotechnology Letters, 24(12), 979-983.
http://dx.doi.org/10.1023/A:1015648508146
---------- CHICAGO ----------
Zinni, M.A., Iglesias, L.E., Iribarren, A.M. "Regioselective preparation of 2′, 3′-di-O-acylribonucleosides carrying lipophilic acyl groups through a lipase-catalysed alcoholysis" . Biotechnology Letters 24, no. 12 (2002) : 979-983.
http://dx.doi.org/10.1023/A:1015648508146
---------- MLA ----------
Zinni, M.A., Iglesias, L.E., Iribarren, A.M. "Regioselective preparation of 2′, 3′-di-O-acylribonucleosides carrying lipophilic acyl groups through a lipase-catalysed alcoholysis" . Biotechnology Letters, vol. 24, no. 12, 2002, pp. 979-983.
http://dx.doi.org/10.1023/A:1015648508146
---------- VANCOUVER ----------
Zinni, M.A., Iglesias, L.E., Iribarren, A.M. Regioselective preparation of 2′, 3′-di-O-acylribonucleosides carrying lipophilic acyl groups through a lipase-catalysed alcoholysis. Biotechnol. Lett. 2002;24(12):979-983.
http://dx.doi.org/10.1023/A:1015648508146