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

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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-acylribonucleosi...

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Detalles Bibliográficos
Autor principal: Zinni, M.A
Otros Autores: Iglesias, L.E, Iribarren, A.M
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2002
Acceso en línea:Registro en Scopus
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Registro en la Biblioteca Digital
Aporte de:Registro referencial: Solicitar el recurso aquí
Biblioteca Central Dr. Luis F. Leloir (FCEN) de Universidad de Buenos Aires
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030 |a BILED 
100 1 |a Zinni, M.A. 
245 1 0 |a Regioselective preparation of 2′, 3′-di-O-acylribonucleosides carrying lipophilic acyl groups through a lipase-catalysed alcoholysis 
260 |c 2002 
270 1 0 |m Iglesias, L.E.; Centro de Estudios e Investigaciones, Universidad Nacional de Quilmes, Roque Saenz Pena 180-(1876) Bernal, Provincia de Buenos Aires, Argentina; email: leiglesias@unq.edu.ar 
506 |2 openaire  |e Política editorial 
504 |a Baker, D.C., Haskell, T.H., Putt, S.R., Sloan, B.J., Prodrugs of 9-(β-D-arabino-furanosyl) adenine 2. Synthesis and evaluation of a number of 2′, 3′- and 3′, 5′-di-O-acylderivatives (1979) J. Med. Chem., 22, pp. 273-279 
504 |a Bornscheuer, U.T., Kazlauskas, R.J., Chemo- and regioselective lipase-catalyzed reactions (1999) Hydrolases in Organic Synthesis, pp. 138-144. , Weinheim: Wiley-VCH 
504 |a Chamberlain, S.D., Moorman, A.R., Jones, L.A., De Miranda, P., Reynolds, D.J., Kozalka, G.W., Krenitsky, T.A., 2′-ester prodrugs of the varicella-zoster antiviral agent, 6-methoxypurine arabinoside (1992) Antiviral Chem. Chemother., 3, pp. 371-378 
504 |a Ciuffreda, P., Casati, S., Santaniello, E., Lipase-catalysed protection of the hydroxy groups of the nucleosides inosine and 2′-deoxyinosine: A new chemoenzymatic synthesis of the antiviral drug 2′, 3′-dideoxyinosine (1999) Bioorg. Med. Chem. Lett., 9, pp. 1577-1582 
504 |a Ciuffreda, P., Casati, S., Santaniello, E., The action of adenosine deaminase (E.C. 3.5.4.4.) on adenosine and deoxyadenosine acetates: The crucial role of the 5′-hydroxy group for the enzyme activity (2000) Tetrahedron, 56, pp. 3239-3243 
504 |a Ferrero, M., Gotor, V., Biocatalytic selective modifications of conventional nucleosides, carbocyclic nucleosides and C-nucleosides (2000) Chem. Rev., 100, pp. 4319-4347 
504 |a Iglesias, L.E., Zinni, M.A., Gallo, M., Iribarren, A.M., Complete and regioselective deacetylation of peracetylated uridines using a lipase (2000) Biotechnol. Lett., 22, pp. 361-365 
504 |a Jones, L.A., Moorman, A.R., Chamberlain, S.D., De Miranda, P., Reynolds, D.J., Bums, C.L., Krenitsky, T.A., Di-and triester prodrugs of the varicella-zoster antiviral agent, 6-methoxypurine arabinoside (1992) J. Med. Chem., 35, pp. 56-63 
504 |a Kim, D., Lee, N., Ryu, D., Kim, Y., Kim, J., Chang, K., Im, G., Locarnini, S., Synthesis and evaluation of 2-amino-9-(3-acyloxy-methyl-4-alkoxy-carbonyloxybut-1-yl)purines and 2-amino-9-(3-alkoxycarbonyloxymethyl-4-alkoxy-carbonyloxybut-1-yl)purines as potential prodrugs of penciclovir (1999) Bioorg. Med. Chem., 7, pp. 1715-1725 
504 |a Mahmoudian, M., Biocatalytic production of chiral pharmaceutical intermediates (2000) Biocat. Biotrans., 18, pp. 105-118 
504 |a Manfredini, S., Baraldi, P.G., Bazzanini, R., Bortolotti, F., Vertuani, S., Ashida, N., Machida, H., Enzymatic synthesis of 2′-O-acyl prodrugs of 1-(β-D-arabinofuranosyl)-5 (E)-(2-bromovinyl)uracil and 2′-O-acyl-araU, -araC and -araA (1998) Antiviral Chem. Chemother., 9, pp. 25-31 
504 |a Périgaud, C., Gosselin, G., Imbach, J.L., Nucleoside analogues as chemotherapeutic agents: A review (1992) Nucleos. Nucleot., 11, pp. 903-945 
504 |a Prasad, A.K., Wengel, J., Enzyme-mediated protecting group chemistry on the hydroxyl groups of nucleosides (1996) Nucleos. Nucleot., 15, pp. 1347-1359 
504 |a Rando, R.F., Nguyen-Ba, N., Development of novel nucleoside analogues for use against drug resistant strains of HIV-1 (2000) Drug Discov. Today, 5, pp. 465-476 
504 |a Roncaglia, D.I., Schmidt, A.M., Iglesias, L.E., Iribarren, A.M., A simple and efficient enzymatic procedure for the deprotection of two base-labile chlorinated purine ribosides (2001) Biotechnol. Lett., 23, pp. 1439-1443 
504 |a Singh, H.K., Cote, G.L., Sikorski, R.S., Enzymatic regioselective deacetylation of 2′, 3′, 5′-tri-O-acylribonucleosides: Enzymatic synthesis of 2′, 3′-di-O-acylribonucleosides (1993) Tetrahedron Lett., 34, pp. 5201-5204 
520 3 |a 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.  |l eng 
536 |a Detalles de la financiación: Universidad Nacional de Quilmes 
536 |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas 
536 |a Detalles de la financiación: We thank UNQ, CONICET and SEPCyT for partial financial support. AMI is research member of CON-ICET. We are grateful to Novo Nordisk (Denmark) for the generous gift of CAL. 
593 |a Centro de Estudios e Investigaciones, Universidad Nacional de Quilmes, Roque Sáenz Peña 180, (1876) Bernal, Prov. de Buenos Aires, Argentina 
593 |a INGEBI (CONICET), Vuelta de Obligado 2490, (1428) Buenos Aires, Argentina 
690 1 0 |a 2′, 3′-DI-O-ACYLRIBONUCLEOSIDES 
690 1 0 |a DEACYLATION 
690 1 0 |a ENZYMATIC ALCOHOLYSIS 
690 1 0 |a LIPASES 
690 1 0 |a NUCLEOSIDES 
690 1 0 |a 2',3' DI O ACYLRIBONUCLEOSIDE 
690 1 0 |a 2',3' DI O DODECANOYLINOSINE 
690 1 0 |a 2',3' DI O DODECANOYLURIDINE 
690 1 0 |a 2',3' DI O HEXANOYLINOSINE 
690 1 0 |a 2',3' DI O HEXANOYLURIDINE 
690 1 0 |a 2',3',5' TRI O DODECANOYLINOSINE 
690 1 0 |a 2',3',5' TRI O DODECANOYLURIDINE 
690 1 0 |a 2',3',5' TRI O HEXANOYLINOSINE 
690 1 0 |a 2',3',5' TRI O HEXANOYLURIDINE 
690 1 0 |a ANTIVIRUS AGENT 
690 1 0 |a INOSINE DERIVATIVE 
690 1 0 |a NUCLEOSIDE ANALOG 
690 1 0 |a RIBONUCLEOSIDE DERIVATIVE 
690 1 0 |a UNCLASSIFIED DRUG 
690 1 0 |a URIDINE DERIVATIVE 
690 1 0 |a ACYLATION 
690 1 0 |a ANTIVIRAL ACTIVITY 
690 1 0 |a ARTICLE 
690 1 0 |a CATALYSIS 
690 1 0 |a CHEMICAL STRUCTURE 
690 1 0 |a CONTROLLED STUDY 
690 1 0 |a ENZYME ACTIVITY 
690 1 0 |a HIGH PERFORMANCE LIQUID CHROMATOGRAPHY 
690 1 0 |a HYDROLYSIS 
690 1 0 |a LIPOPHILICITY 
690 1 0 |a NONHUMAN 
690 1 0 |a THIN LAYER CHROMATOGRAPHY 
690 1 0 |a CANDIDA 
690 1 0 |a CANDIDA ANTARCTICA 
700 1 |a Iglesias, L.E. 
700 1 |a Iribarren, A.M. 
773 0 |d 2002  |g v. 24  |h pp. 979-983  |k n. 12  |p Biotechnol. Lett.  |x 01415492  |w (AR-BaUEN)CENRE-148  |t Biotechnology Letters 
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856 4 0 |u https://doi.org/10.1023/A:1015648508146  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_01415492_v24_n12_p979_Zinni  |y Handle 
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999 |c 81290 

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