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-acylribonucleosi...

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Autores principales:	Zinni, M.A., Iglesias, L.E., Iribarren, A.M.
Formato:	JOUR
Materias:	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
Acceso en línea:	http://hdl.handle.net/20.500.12110/paper_01415492_v24_n12_p979_Zinni
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

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spelling	todo:paper_01415492_v24_n12_p979_Zinni2023-10-03T14:58:39Z Regioselective preparation of 2′, 3′-di-O-acylribonucleosides carrying lipophilic acyl groups through a lipase-catalysed alcoholysis Zinni, M.A. Iglesias, L.E. Iribarren, A.M. 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 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_01415492_v24_n12_p979_Zinni
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	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
spellingShingle	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 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
topic_facet	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
description	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.
format	JOUR
author	Zinni, M.A. Iglesias, L.E. Iribarren, A.M.
author_facet	Zinni, M.A. Iglesias, L.E. Iribarren, A.M.
author_sort	Zinni, M.A.
title	Regioselective preparation of 2′, 3′-di-O-acylribonucleosides carrying lipophilic acyl groups through a lipase-catalysed alcoholysis
title_short	Regioselective preparation of 2′, 3′-di-O-acylribonucleosides carrying lipophilic acyl groups through a lipase-catalysed alcoholysis
title_full	Regioselective preparation of 2′, 3′-di-O-acylribonucleosides carrying lipophilic acyl groups through a lipase-catalysed alcoholysis
title_fullStr	Regioselective preparation of 2′, 3′-di-O-acylribonucleosides carrying lipophilic acyl groups through a lipase-catalysed alcoholysis
title_full_unstemmed	Regioselective preparation of 2′, 3′-di-O-acylribonucleosides carrying lipophilic acyl groups through a lipase-catalysed alcoholysis
title_sort	regioselective preparation of 2′, 3′-di-o-acylribonucleosides carrying lipophilic acyl groups through a lipase-catalysed alcoholysis
url	http://hdl.handle.net/20.500.12110/paper_01415492_v24_n12_p979_Zinni
work_keys_str_mv	AT zinnima regioselectivepreparationof23dioacylribonucleosidescarryinglipophilicacylgroupsthroughalipasecatalysedalcoholysis AT iglesiasle regioselectivepreparationof23dioacylribonucleosidescarryinglipophilicacylgroupsthroughalipasecatalysedalcoholysis AT iribarrenam regioselectivepreparationof23dioacylribonucleosidescarryinglipophilicacylgroupsthroughalipasecatalysedalcoholysis
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Regioselective preparation of 2′, 3′-di-O-acylribonucleosides carrying lipophilic acyl groups through a lipase-catalysed alcoholysis

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