Deprotection of peracetylated methyl D-ribosides through enzymatic alcoholysis: Different recognition of the anomers

Autores
Iñigo, Sabrina; Taverna Porro, Marisa Lia; Montserrat, Javier Marcelo; Iglesias, Luis Emilio; Iribarren, Adolfo Marcelo
Año de publicación
2005
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The anomers methyl 2,3,5-tri-O-acetyl-α-d-ribofuranoside and methyl 2,3,5-tri-O-acetyl-β-d-ribofuranoside showed a different behaviour in the Candida antarctica B lipase-catalysed alcoholysis. While the enzymatic deprotection of the former proceeded regioselectively affording methyl 2,3-di-O-acetyl-α-d-ribofuranoside in 81% yield in 3 h at 45°C showing no further transformation, the alcoholysis of the β-diasteromer was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the α epimer, full deacetylated methyl β-d-ribofuranoside was quantitatively formed at long reaction times (5 days).
Fil: Iñigo, Sabrina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Quilmes; Argentina
Fil: Taverna Porro, Marisa Lia. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Ingeniería Genética y Biología Molecular "Dr. Héctor N. Torres"; Argentina
Fil: Montserrat, Javier 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 General Sarmiento. Instituto de Ciencias; Argentina
Fil: Iglesias, Luis Emilio. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Quilmes; Argentina
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; Argentina
Materia
Deacetylation
Enzymatic Alcoholysis
Lipases
Regioselectivity
Ribosides
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/80102
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Deprotection of peracetylated methyl D-ribosides through enzymatic alcoholysis: Different recognition of the anomersIñigo, SabrinaTaverna Porro, Marisa LiaMontserrat, Javier MarceloIglesias, Luis EmilioIribarren, Adolfo MarceloDeacetylationEnzymatic AlcoholysisLipasesRegioselectivityRibosideshttps://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1The anomers methyl 2,3,5-tri-O-acetyl-α-d-ribofuranoside and methyl 2,3,5-tri-O-acetyl-β-d-ribofuranoside showed a different behaviour in the Candida antarctica B lipase-catalysed alcoholysis. While the enzymatic deprotection of the former proceeded regioselectively affording methyl 2,3-di-O-acetyl-α-d-ribofuranoside in 81% yield in 3 h at 45°C showing no further transformation, the alcoholysis of the β-diasteromer was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the α epimer, full deacetylated methyl β-d-ribofuranoside was quantitatively formed at long reaction times (5 days).Fil: Iñigo, Sabrina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Quilmes; ArgentinaFil: Taverna Porro, Marisa Lia. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Ingeniería Genética y Biología Molecular "Dr. Héctor N. Torres"; ArgentinaFil: Montserrat, Javier 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 General Sarmiento. Instituto de Ciencias; ArgentinaFil: Iglesias, Luis Emilio. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Quilmes; ArgentinaFil: 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; ArgentinaElsevier Science2005-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/80102Iñigo, Sabrina; Taverna Porro, Marisa Lia; Montserrat, Javier Marcelo; Iglesias, Luis Emilio; Iribarren, Adolfo Marcelo; Deprotection of peracetylated methyl D-ribosides through enzymatic alcoholysis: Different recognition of the anomers; Elsevier Science; Journal of Molecular Catalysis B: Enzymatic; 35; 1-3; 8-2005; 70-731381-1177CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1381117705000809info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molcatb.2005.05.010info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:47:46Zoai:ri.conicet.gov.ar:11336/80102instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-03 09:47:46.918CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Deprotection of peracetylated methyl D-ribosides through enzymatic alcoholysis: Different recognition of the anomers
title Deprotection of peracetylated methyl D-ribosides through enzymatic alcoholysis: Different recognition of the anomers
spellingShingle Deprotection of peracetylated methyl D-ribosides through enzymatic alcoholysis: Different recognition of the anomers
Iñigo, Sabrina
Deacetylation
Enzymatic Alcoholysis
Lipases
Regioselectivity
Ribosides
title_short Deprotection of peracetylated methyl D-ribosides through enzymatic alcoholysis: Different recognition of the anomers
title_full Deprotection of peracetylated methyl D-ribosides through enzymatic alcoholysis: Different recognition of the anomers
title_fullStr Deprotection of peracetylated methyl D-ribosides through enzymatic alcoholysis: Different recognition of the anomers
title_full_unstemmed Deprotection of peracetylated methyl D-ribosides through enzymatic alcoholysis: Different recognition of the anomers
title_sort Deprotection of peracetylated methyl D-ribosides through enzymatic alcoholysis: Different recognition of the anomers
dc.creator.none.fl_str_mv Iñigo, Sabrina
Taverna Porro, Marisa Lia
Montserrat, Javier Marcelo
Iglesias, Luis Emilio
Iribarren, Adolfo Marcelo
author Iñigo, Sabrina
author_facet Iñigo, Sabrina
Taverna Porro, Marisa Lia
Montserrat, Javier Marcelo
Iglesias, Luis Emilio
Iribarren, Adolfo Marcelo
author_role author
author2 Taverna Porro, Marisa Lia
Montserrat, Javier Marcelo
Iglesias, Luis Emilio
Iribarren, Adolfo Marcelo
author2_role author
author
author
author
dc.subject.none.fl_str_mv Deacetylation
Enzymatic Alcoholysis
Lipases
Regioselectivity
Ribosides
topic Deacetylation
Enzymatic Alcoholysis
Lipases
Regioselectivity
Ribosides
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The anomers methyl 2,3,5-tri-O-acetyl-α-d-ribofuranoside and methyl 2,3,5-tri-O-acetyl-β-d-ribofuranoside showed a different behaviour in the Candida antarctica B lipase-catalysed alcoholysis. While the enzymatic deprotection of the former proceeded regioselectively affording methyl 2,3-di-O-acetyl-α-d-ribofuranoside in 81% yield in 3 h at 45°C showing no further transformation, the alcoholysis of the β-diasteromer was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the α epimer, full deacetylated methyl β-d-ribofuranoside was quantitatively formed at long reaction times (5 days).
Fil: Iñigo, Sabrina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Quilmes; Argentina
Fil: Taverna Porro, Marisa Lia. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Ingeniería Genética y Biología Molecular "Dr. Héctor N. Torres"; Argentina
Fil: Montserrat, Javier 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 General Sarmiento. Instituto de Ciencias; Argentina
Fil: Iglesias, Luis Emilio. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Quilmes; Argentina
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; Argentina
description The anomers methyl 2,3,5-tri-O-acetyl-α-d-ribofuranoside and methyl 2,3,5-tri-O-acetyl-β-d-ribofuranoside showed a different behaviour in the Candida antarctica B lipase-catalysed alcoholysis. While the enzymatic deprotection of the former proceeded regioselectively affording methyl 2,3-di-O-acetyl-α-d-ribofuranoside in 81% yield in 3 h at 45°C showing no further transformation, the alcoholysis of the β-diasteromer was less selective. For this anomer, mixtures of partially acetylated products were formed, but contrasting to the α epimer, full deacetylated methyl β-d-ribofuranoside was quantitatively formed at long reaction times (5 days).
publishDate 2005
dc.date.none.fl_str_mv 2005-08
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/80102
Iñigo, Sabrina; Taverna Porro, Marisa Lia; Montserrat, Javier Marcelo; Iglesias, Luis Emilio; Iribarren, Adolfo Marcelo; Deprotection of peracetylated methyl D-ribosides through enzymatic alcoholysis: Different recognition of the anomers; Elsevier Science; Journal of Molecular Catalysis B: Enzymatic; 35; 1-3; 8-2005; 70-73
1381-1177
CONICET Digital
CONICET
url http://hdl.handle.net/11336/80102
identifier_str_mv Iñigo, Sabrina; Taverna Porro, Marisa Lia; Montserrat, Javier Marcelo; Iglesias, Luis Emilio; Iribarren, Adolfo Marcelo; Deprotection of peracetylated methyl D-ribosides through enzymatic alcoholysis: Different recognition of the anomers; Elsevier Science; Journal of Molecular Catalysis B: Enzymatic; 35; 1-3; 8-2005; 70-73
1381-1177
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1381117705000809
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molcatb.2005.05.010
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.13397

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