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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ftunibueairesbd:todo:paper_01415492_v24_n12_p979_Zinni 2023-10-29T02:31:55+01:00 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. https://hdl.handle.net/20.500.12110/paper_01415492_v24_n12_p979_Zinni unknown http://hdl.handle.net/20.500.12110/paper_01415492_v24_n12_p979_Zinni info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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 JOUR ftunibueairesbd https://doi.org/20.500.12110/paper_01415492_v24_n12_p979_Zinni 2023-10-05T01:41:35Z 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. Journal/Newspaper Antarc* Antarctica Biblioteca Digital FCEN-UBA (Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires) |
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Open Polar |
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Biblioteca Digital FCEN-UBA (Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires) |
op_collection_id |
ftunibueairesbd |
language |
unknown |
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 |
Journal/Newspaper |
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 |
https://hdl.handle.net/20.500.12110/paper_01415492_v24_n12_p979_Zinni |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
http://hdl.handle.net/20.500.12110/paper_01415492_v24_n12_p979_Zinni |
op_rights |
info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar |
op_doi |
https://doi.org/20.500.12110/paper_01415492_v24_n12_p979_Zinni |
_version_ |
1781052800870907904 |