Enzymatic regioselective and complete deacetylation of two arabinonucleosides
Candida antarctica lipase B (CAL-B)-catalysed regioselective deacetylation of 2′,3′,5′-tri- O-acetyl-1-β- d-arabinofuranosyluracil (1) and 2′,3′,5′-tri- O-acetyl-9-β- d-arabinofuranosyladenine (2) was studied. The choice of the reaction medium allowed the regioselective formation of products bearing...
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ftconicet:oai:ri.conicet.gov.ar:11336/190764 2023-10-09T21:47:06+02:00 Enzymatic regioselective and complete deacetylation of two arabinonucleosides Sabaini, María Belén Zinni, María A. Mohorčič, Martina Friedrich, Jožefa Iribarren, Adolfo Marcelo Iglesias, Luis Emilio application/pdf http://hdl.handle.net/11336/190764 eng eng Elsevier Science info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1381117709002641 info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molcatb.2009.10.011 http://hdl.handle.net/11336/190764 Sabaini, María Belén; Zinni, María A.; Mohorčič, Martina; Friedrich, Jožefa; Iribarren, Adolfo Marcelo; et al.; Enzymatic regioselective and complete deacetylation of two arabinonucleosides; Elsevier Science; Journal of Molecular Catalysis B: Enzymatic; 62; 3-4; 3-2010; 225-229 1381-1177 CONICET Digital CONICET info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ KERATINASE LIPASE NUCLEOSIDES PRODRUGS REGIOSELECTIVITY https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 info:eu-repo/semantics/article info:ar-repo/semantics/artículo info:eu-repo/semantics/publishedVersion ftconicet https://doi.org/10.1016/j.molcatb.2009.10.011 2023-09-24T20:05:59Z Candida antarctica lipase B (CAL-B)-catalysed regioselective deacetylation of 2′,3′,5′-tri- O-acetyl-1-β- d-arabinofuranosyluracil (1) and 2′,3′,5′-tri- O-acetyl-9-β- d-arabinofuranosyladenine (2) was studied. The choice of the reaction medium allowed the regioselective formation of products bearing different degree of acetylation: in isopropanol, CAL-B catalysed the formation of the corresponding 2′- O-acetylated arabinonucleosides, while hydrolyses afforded the 2′,3′-di- O-acetylated products. In particular, the procedure herein described allows a simple and efficient preparation of the reported vidarabine prodrug 2′,3′-di- O-acetyl-9-β- d-arabinofuranosyladenine, avoiding the utilisation of protective groups. Moreover, to achieve full deacetylation of the assayed substrates, a set of commercial hydrolases and fungal keratinases from Doratomyces microsporus (DMK) and Paecilomyces marquandii (PMK) were tested. While only PMK and DMK catalysed the quantitative complete deacetylation of 1, DMK accomplished full deacetylation of 2 in shorter time than the other assayed enzymes. Fil: Sabaini, María Belén. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina Fil: Zinni, María A. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina Fil: Mohorčič, Martina. National Institute Of Chemistry; Eslovenia Fil: Friedrich, Jožefa. National Institute Of Chemistry; Eslovenia Fil: Iribarren, Adolfo Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Ingeniería Genética y Biología Molecular "Dr. Héctor N. Torres"; Argentina. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina Fil: Iglesias, Luis Emilio. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina Article in Journal/Newspaper Antarc* Antarctica CONICET Digital (Consejo Nacional de Investigaciones Científicas y Técnicas) Argentina Martina ENVELOPE(-75.217,-75.217,-69.783,-69.783) Quilmes ENVELOPE(-55.617,-55.617,-63.233,-63.233) Journal of Molecular Catalysis B: Enzymatic 62 3-4 225 229 |
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Open Polar |
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CONICET Digital (Consejo Nacional de Investigaciones Científicas y Técnicas) |
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ftconicet |
language |
English |
topic |
KERATINASE LIPASE NUCLEOSIDES PRODRUGS REGIOSELECTIVITY https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
spellingShingle |
KERATINASE LIPASE NUCLEOSIDES PRODRUGS REGIOSELECTIVITY https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 Sabaini, María Belén Zinni, María A. Mohorčič, Martina Friedrich, Jožefa Iribarren, Adolfo Marcelo Iglesias, Luis Emilio Enzymatic regioselective and complete deacetylation of two arabinonucleosides |
topic_facet |
KERATINASE LIPASE NUCLEOSIDES PRODRUGS REGIOSELECTIVITY https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
description |
Candida antarctica lipase B (CAL-B)-catalysed regioselective deacetylation of 2′,3′,5′-tri- O-acetyl-1-β- d-arabinofuranosyluracil (1) and 2′,3′,5′-tri- O-acetyl-9-β- d-arabinofuranosyladenine (2) was studied. The choice of the reaction medium allowed the regioselective formation of products bearing different degree of acetylation: in isopropanol, CAL-B catalysed the formation of the corresponding 2′- O-acetylated arabinonucleosides, while hydrolyses afforded the 2′,3′-di- O-acetylated products. In particular, the procedure herein described allows a simple and efficient preparation of the reported vidarabine prodrug 2′,3′-di- O-acetyl-9-β- d-arabinofuranosyladenine, avoiding the utilisation of protective groups. Moreover, to achieve full deacetylation of the assayed substrates, a set of commercial hydrolases and fungal keratinases from Doratomyces microsporus (DMK) and Paecilomyces marquandii (PMK) were tested. While only PMK and DMK catalysed the quantitative complete deacetylation of 1, DMK accomplished full deacetylation of 2 in shorter time than the other assayed enzymes. Fil: Sabaini, María Belén. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina Fil: Zinni, María A. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina Fil: Mohorčič, Martina. National Institute Of Chemistry; Eslovenia Fil: Friedrich, Jožefa. National Institute Of Chemistry; Eslovenia Fil: Iribarren, Adolfo Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Ingeniería Genética y Biología Molecular "Dr. Héctor N. Torres"; Argentina. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina Fil: Iglesias, Luis Emilio. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Quilmes. Departamento de Ciencia y Tecnología; Argentina |
format |
Article in Journal/Newspaper |
author |
Sabaini, María Belén Zinni, María A. Mohorčič, Martina Friedrich, Jožefa Iribarren, Adolfo Marcelo Iglesias, Luis Emilio |
author_facet |
Sabaini, María Belén Zinni, María A. Mohorčič, Martina Friedrich, Jožefa Iribarren, Adolfo Marcelo Iglesias, Luis Emilio |
author_sort |
Sabaini, María Belén |
title |
Enzymatic regioselective and complete deacetylation of two arabinonucleosides |
title_short |
Enzymatic regioselective and complete deacetylation of two arabinonucleosides |
title_full |
Enzymatic regioselective and complete deacetylation of two arabinonucleosides |
title_fullStr |
Enzymatic regioselective and complete deacetylation of two arabinonucleosides |
title_full_unstemmed |
Enzymatic regioselective and complete deacetylation of two arabinonucleosides |
title_sort |
enzymatic regioselective and complete deacetylation of two arabinonucleosides |
publisher |
Elsevier Science |
url |
http://hdl.handle.net/11336/190764 |
long_lat |
ENVELOPE(-75.217,-75.217,-69.783,-69.783) ENVELOPE(-55.617,-55.617,-63.233,-63.233) |
geographic |
Argentina Martina Quilmes |
geographic_facet |
Argentina Martina Quilmes |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1381117709002641 info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molcatb.2009.10.011 http://hdl.handle.net/11336/190764 Sabaini, María Belén; Zinni, María A.; Mohorčič, Martina; Friedrich, Jožefa; Iribarren, Adolfo Marcelo; et al.; Enzymatic regioselective and complete deacetylation of two arabinonucleosides; Elsevier Science; Journal of Molecular Catalysis B: Enzymatic; 62; 3-4; 3-2010; 225-229 1381-1177 CONICET Digital CONICET |
op_rights |
info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
op_doi |
https://doi.org/10.1016/j.molcatb.2009.10.011 |
container_title |
Journal of Molecular Catalysis B: Enzymatic |
container_volume |
62 |
container_issue |
3-4 |
container_start_page |
225 |
op_container_end_page |
229 |
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1779309837790740480 |